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Old page wikitext, before the edit (old_wikitext ) | '{{short description|Any molecule with a cyano group (–C≡N)}}
{{About|the class of chemical compounds}}
{{distinguish|Nitrile}}
{{Chembox
| ImageFile = Cyanide-montage.png
| ImageAlt = Space-filling model of the cyanide anion: carbon bound to smaller nitrogen atom
| Name=Cyanide anion
| PIN = Cyanide
| SystematicName = Nitridocarbonate(II)
| IUPACName =
| OtherNames =
|Section1 = {{Chembox Identifiers
| CASNo = 57-12-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = OXN4E7L11K
| PubChem = 5975
| ChEBI = 17514
| SMILES = [C-]#N
| ChemSpiderID = 5755
| InChI = 1S/CN/c1-2/q-1
| InChIKey = XFXPMWWXUTWYJX-UHFFFAOYSA-N
}}
|Section2 = {{Chembox Properties
| Formula = {{chem2|CN−}}
| C=1|N=1
| Appearance =
| Solubility =
| ConjugateAcid = [[Hydrogen cyanide]]}}
|Section3 = {{Chembox Hazards
| MainHazards = The cyanide ion {{chem2|CN−}} is one of the most poisonous chemicals. It may cause death in minutes.
| FlashPt =
| AutoignitionPt = }}
}}
In [[chemistry]], '''cyanide''' ({{ety|el|kyanos|[[Prussian blue|dark blue]]}}) is a [[chemical compound]] that contains a {{chem2|C\tN}} [[functional group]]. This group, known as the '''cyano group''', consists of a [[carbon]] atom [[triple-bond]]ed to a [[nitrogen]] atom.<ref>{{cite journal|url=http://goldbook.iupac.org/C01486.html |title=cyanides|website=[[IUPAC Gold Book]] |date=2014 |doi=10.1351/goldbook.C01486 |doi-access=free }}</ref>
In [[Inorganic compound|inorganic]] cyanides, the cyanide group is present as the cyanide anion {{chem2|−C\tN}}. This anion is [[Cyanide poisoning|extremely poisonous]]. Soluble [[Salt (chemistry)|salts]] such as [[sodium cyanide]] (NaCN) and [[potassium cyanide]] (KCN) are highly toxic.<ref name="CMC">{{Cite web| url=http://www.cyanidecode.org/cyanide_environmental.php| title=Environmental and Health Effects of Cyanide| publisher=International Cyanide Management Institute| year=2006| access-date=4 August 2009| archive-date=30 November 2012| archive-url=https://web.archive.org/web/20121130094124/http://www.cyanidecode.org/cyanide_environmental.php| url-status=dead}}</ref> [[Hydrocyanic acid]], also known as hydrogen cyanide, or HCN, is a highly [[Volatility (chemistry)|volatile]] liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.
[[Organic compound|Organic]] cyanides are usually called [[nitrile]]s. In nitriles, the {{chem2|\sC\tN}} group is linked by a single [[covalent bond]] to carbon. For example, in [[acetonitrile]] ({{chem2|CH3\sC\tN}}), the cyanide group is bonded to [[methyl]] ({{chem2|\sCH3}}). Although nitriles generally do not release cyanide ions, the [[cyanohydrin]]s do and are thus toxic.
==Bonding==
The cyanide ion {{chem2|−C\tN}} is [[isoelectronic]] with [[carbon monoxide]] {{chem2|-C\tO+}} and with molecular [[nitrogen]] N≡N. A triple bond exists between C and N. The negative charge is concentrated on [[carbon]] C.<ref>Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. {{ISBN|0-7506-3365-4}}.{{page needed|date=July 2015}}</ref><ref>G. L. Miessler and D. A. Tarr "Inorganic Chemistry" 3rd Ed, Pearson/Prentice Hall publisher, {{ISBN|0-13-035471-6}}.{{page needed|date=July 2015}}</ref>
==Occurrence==
===In nature===
[[File:Removal of cyanide poison from cassava.jpg|thumb|left|Removal of cyanide from [[cassava]] in [[Nigeria]].]]
Cyanides are produced by certain [[bacterium|bacteria]], [[fungi]], and [[algae]]. It is an [[antifeedant]] in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of [[bitter almond]]s, [[apricot]]s, [[apple]]s, and [[peach]]es.<ref>{{Cite web|url=https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=71&tid=19 |title=ToxFAQs for Cyanide |access-date=2008-06-28 |date = July 2006|publisher=[[Agency for Toxic Substances and Disease Registry]]}}</ref> Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to [[sugar]] molecules in the form of cyanogenic [[glycoside]]s and defend the plant against [[herbivore]]s. [[Cassava]] roots (also called manioc), an important [[potato]]-like food grown in tropical countries (and the base from which [[tapioca]] is made), also contain cyanogenic glycosides.<ref>{{Cite journal|first=J. |last=Vetter |title=Plant cyanogenic glycosides |journal=Toxicon |year=2000 |volume=38 |pages=11–36 |doi=10.1016/S0041-0101(99)00128-2 |pmid=10669009 |issue=1}}</ref><ref name=jones>{{Cite journal|first=D. A. |last=Jones |title= Why are so many food plants cyanogenic? |journal=[[Phytochemistry (journal)|Phytochemistry]] |year=1998 |volume=47 |pages=155–162 |doi=10.1016/S0031-9422(97)00425-1 |pmid=9431670 |issue=2|bibcode=1998PChem..47..155J }}</ref>
The [[Madagascar]] bamboo ''[[Cathariostachys madagascariensis]]'' produces cyanide as a deterrent to grazing. In response, the [[golden bamboo lemur]], which eats the bamboo, has developed a high tolerance to cyanide.
The [[hydrogenase]] enzymes contain cyanide [[ligand]]s attached to iron in their active sites. The biosynthesis of cyanide in the [[NiFe hydrogenase]]s proceeds from [[carbamoyl phosphate]], which converts to [[cystein]]yl [[thiocyanate]], the {{chem2|CN−}} donor.<ref>{{cite journal |last1=Reissmann |first1=Stefanie |last2=Hochleitner |first2=Elisabeth |last3=Wang |first3=Haofan |last4=Paschos |first4=Athanasios |last5=Lottspeich |first5=Friedrich |last6=Glass |first6=Richard S. |last7=Böck |first7=August |title=Taming of a Poison: Biosynthesis of the NiFe-Hydrogenase Cyanide Ligands |journal=Science |volume=299 |issue=5609 |pages=1067–1070 |year=2003 |pmid=12586941 |doi=10.1126/science.1080972 |bibcode=2003Sci...299.1067R |s2cid=20488694 |url=http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf |archive-url=https://web.archive.org/web/20201123134841/http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf |archive-date=2020-11-23 |url-status=live }}</ref>
===Interstellar medium===
The [[cyanide radical]] <sup>•</sup>CN has been identified in [[interstellar space]].<ref>{{Cite journal |last=Pieniazek |first=Piotr A. |author2=Bradforth, Stephen E. |author3=Krylov, Anna I. |title=Spectroscopy of the Cyano Radical in an Aqueous Environment |date=2005-12-07 |pages=4854–4865 |issue=14 |volume=110 |url=http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf |journal=The Journal of Physical Chemistry A |pmid=16599455 |doi=10.1021/jp0545952 |bibcode=2006JPCA..110.4854P |access-date=2008-08-23 |archive-url=https://web.archive.org/web/20080911131555/http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf |archive-date=2008-09-11 |url-status=dead }}</ref> [[Cyanogen]], {{chem2|(CN)2}}, is used to measure the temperature of [[Molecular cloud|interstellar gas clouds]].<ref>{{cite journal |title = Interstellar Cyanogen and the Temperature of the Cosmic Microwave Background Radiation |author1=Roth, K. C. |author2=Meyer, D. M. |author3=Hawkins, I.|author3-link=Isabel Hawkins |journal = The Astrophysical Journal |year = 1993 |volume = 413 |issue = 2 |pages = L67–L71 |doi = 10.1086/186961 |bibcode = 1993ApJ...413L..67R |url = http://articles.adsabs.harvard.edu/cgi-bin/nph-iarticle_query?1993ApJ...413L..67R&data_type=PDF_HIGH&whole_paper=YES&type=PRINTER&filetype=.pdf }}</ref>
===Pyrolysis and combustion product===
Hydrogen cyanide is produced by the combustion or [[pyrolysis]] of certain materials under oxygen-deficient conditions. For example, it can be detected in the [[exhaust gas|exhaust]] of [[internal combustion engine]]s and [[tobacco]] smoke. Certain [[plastic]]s, especially those derived from [[acrylonitrile]], release hydrogen cyanide when heated or burnt.<ref name="CDC"/>
===Organic derivatives===
{{Main|Nitriles}}
{{see also|Isocyanide}}
In [[IUPAC nomenclature of organic chemistry|IUPAC nomenclature]], [[organic compound]]s that have a {{chem2|\sC\tN}} [[functional group]] are called [[nitrile]]s.<ref>[[IUPAC Gold Book]] [http://goldbook.iupac.org/N04151.html ''nitriles'']</ref><ref>NCBI-MeSH [https://www.ncbi.nlm.nih.gov/mesh/68009570 ''Nitriles'']</ref> An example of a nitrile is [[acetonitrile]], {{chem2|CH3\sC\tN}}. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl {{chem2|\sOH}} and cyanide {{chem2|\sCN}} bonded to the same carbon atom is called [[cyanohydrin]] ({{chem2|R2C(OH)CN}}). Unlike nitriles, cyanohydrins do release poisonous [[hydrogen cyanide]].
==Reactions==
===Protonation===
Cyanide is basic. The p''K''<sub>a</sub> of hydrogen cyanide is 9.21. Thus, addition of [[acids]] stronger than hydrogen cyanide to solutions of cyanide salts releases [[hydrogen cyanide]].
===Hydrolysis===
Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes [[hydrolysis]] to give [[ammonia]] and [[formate]], which are far less toxic than cyanide:<ref name=Ullmann/>
:{{chem2|CN- + 2 H2O → HCO2- + NH3}}
[[Cyanide hydrolase]] is an [[enzyme]] that catalyzes this reaction.
===Alkylation===
Because of the cyanide anion's high [[nucleophile|nucleophilicity]], cyano groups are readily introduced into organic molecules by displacement of a [[halide]] group (e.g., the [[chloride]] on [[methyl chloride]]). In general, organic cyanides are called nitriles. In organic synthesis, cyanide is a C-1 [[synthon]]; i.e., it can be used to lengthen a carbon chain by one, while retaining the ability to be [[wiktionary:functionalize|functionalized]].<ref>{{Ullmann|doi=10.1002/14356007.a17_363|title=Nitriles|year=2000|last1=Pollak|first1=Peter|last2=Romeder|first2=Gérard|last3=Hagedorn|first3=Ferdinand|last4=Gelbke|first4=Heinz-Peter|isbn=3-527-30673-0}}</ref>
:{{chem2|RX + CN- → RCN + X-}}
===Redox===
The cyanide ion is a [[reducing agent|reductant]] and is [[oxidation|oxidized]] by strong [[oxidizing agent]]s such as molecular [[chlorine]] ({{chem2|Cl2}}), [[hypochlorite]] ({{chem2|ClO-}}), and [[hydrogen peroxide]] ({{chem2|H2O2}}). These oxidizers are used to destroy cyanides in [[effluent]]s from [[gold mining]].<ref name="Young_1995">Young, C. A., & Jordan, T. S. (1995, May). Cyanide remediation: current and past technologies. In: Proceedings of the 10th Annual Conference on Hazardous Waste Research (pp. 104–129). Kansas State University: Manhattan, KS. https://engg.ksu.edu/HSRC/95Proceed/young.pdf</ref><ref name="SRK">{{Cite web |title=Cyanide Destruction {{!}} SRK Consulting |author=Dmitry Yermakov |work=srk.com |date= |access-date=2 March 2021 |url= https://www.srk.com/en/publications/cyanide-destruction |language=English}}</ref><ref name="Botz">Botz Michael M. Overview of cyanide treatment methods. Elbow Creek Engineering, Inc. http://www.botz.com/MEMCyanideTreatment.pdf</ref>
===Metal complexation===
The cyanide anion reacts with [[transition metals]] to form [[Cyanometalate|M-CN bonds]]. This reaction is the basis of cyanide's toxicity.<ref>Sharpe, A. G. The Chemistry of Cyano Complexes of the Transition Metals; Academic Press: London, 1976{{page needed|date=July 2015}}</ref> The high affinities of metals for this [[anion]] can be attributed to its negative charge, compactness, and ability to engage in π-bonding.
Among the most important cyanide coordination compounds are the [[potassium ferrocyanide]] and the pigment [[Prussian blue]], which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.<ref name=Holl>{{ cite book |author1=Holleman, A. F. |author2=Wiberg, E. | title = Inorganic Chemistry | publisher = Academic Press | location = San Diego | year = 2001 | isbn = 978-0-12-352651-9 }}</ref>
Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to [[blueprints]], [[bluing (fabric)|bluing]], and [[cyanotype]]s.
==Manufacture==
{{main|Hydrogen cyanide#Production and synthesis}}
The principal process used to manufacture cyanides is the [[Andrussow process]] in which gaseous [[hydrogen cyanide]] is produced from [[methane]] and [[ammonia]] in the presence of [[oxygen]] and a [[platinum]] [[catalyst]].<ref>{{cite journal
|title=Über die schnell verlaufenden katalytischen Prozesse in strömenden Gasen und die Ammoniak-Oxydation (V) |trans-title=About the quicka catalytic processes in flowing gases and the ammonia oxidation (V) |language=de |author-link1=Leonid Andrussow |first1=Leonid |last1=Andrussow |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=60 |issue=8 |pages=2005–2018 |year=1927 |doi=10.1002/cber.19270600857 }}</ref><ref>{{cite journal |title=Über die katalytische Oxydation von Ammoniak-Methan-Gemischen zu Blausäure |trans-title=About the catalytic oxidation of ammonia-methane mixtures to cyanide |language=de |first1=L. |last1=Andrussow |journal=[[Angewandte Chemie]] |volume=48 |issue=37 |pages=593–595 |year=1935 |doi=10.1002/ange.19350483702 |bibcode=1935AngCh..48..593A }}</ref>
:{{chem2|2 CH4 + 2 NH3 + 3 O2 → 2 HCN + 6 H2O}}
Sodium cyanide, the precursor to most cyanides, is produced by treating [[hydrogen cyanide]] with [[sodium hydroxide]]:<ref name=Ullmann />
:{{chem2|HCN + NaOH → NaCN + H2O}}
==Toxicity==
{{Main|Cyanide poisoning}}
Many cyanides are highly toxic. The cyanide anion is an [[enzyme inhibitor|inhibitor]] of the [[enzyme]] [[cytochrome c oxidase]] (also known as aa<sub>3</sub>), the fourth complex of the [[electron transport chain]] found in the [[Inner mitochondrial membrane|inner membrane]] of the [[mitochondria]] of [[Eukaryote|eukaryotic]] cells. It attaches to the iron within this protein. The binding of cyanide to this enzyme prevents transport of electrons from [[cytochrome c]] to oxygen. As a result, the electron transport chain is disrupted, meaning that the cell can no longer aerobically produce [[adenosine triphosphate|ATP]] for energy.<ref>{{cite book|last1=Nelson|first1=David L.|last2=Cox|first2=Michael M.|title=Lehniger Principles of Biochemistry|publisher=[[Worth Publishers]]|year=2000|location=New York|edition=3rd|isbn=978-1-57259-153-0|pages=[https://archive.org/details/lehningerprincip01lehn/page/668 668,670–71,676]|url=https://archive.org/details/lehningerprincip01lehn/page/668}}</ref> Tissues that depend highly on [[aerobic respiration]], such as the [[central nervous system]] and the [[heart]], are particularly affected. This is an example of [[histotoxic hypoxia]].<ref name=Biller>{{cite book
|title=Interface of neurology and internal medicine
|edition=illustrated
|first1=José
|last1=Biller
|publisher=Lippincott Williams & Wilkins
|year=2007
|isbn=978-0-7817-7906-7
|chapter=163
|page=939
|chapter-url=https://books.google.com/books?id=SRIvmTVcYBwC&pg=PA939}}
</ref>
The most hazardous compound is [[hydrogen cyanide]], which is a gas and kills by inhalation. For this reason, an air respirator supplied by an external oxygen source must be worn when working with hydrogen cyanide.<ref name="CDC">{{Cite web|url=https://emergency.cdc.gov/agent/cyanide/basics/facts.asp|title=Facts about cyanide:Where cyanide is found and how it is used|last=Anon|date=June 27, 2013|work=CDC Emergency preparedness and response|publisher=Centers for Disease Control and Prevention|access-date=10 December 2016}}</ref> Hydrogen cyanide is produced by adding acid to a solution containing a cyanide salt. Alkaline solutions of cyanide are safer to use because they do not evolve hydrogen cyanide gas. Hydrogen cyanide may be produced in the combustion of [[polyurethane]]s; for this reason, polyurethanes are not recommended for use in domestic and aircraft furniture. Oral ingestion of a small quantity of solid cyanide or a cyanide solution of as little as 200 mg, or exposure to airborne cyanide of 270 [[parts per million|ppm]], is sufficient to cause death within minutes.<ref name=Biller/>
Organic [[nitrile]]s do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as [[trimethylsilyl cyanide]] {{chem2|(CH3)3SiCN}} readily release HCN or the cyanide ion upon contact with water.<ref>{{cite web |url=https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf |archive-url=https://ghostarchive.org/archive/20221010/https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf |archive-date=2022-10-10 |url-status=live |title=MSDS of trimethylsilyl cyanide |publisher=Gelest Inc |date=2008 |access-date=2022-08-16}}</ref>
===Antidote===
[[Hydroxocobalamin]] reacts with cyanide to form [[cyanocobalamin]], which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.<ref>{{EMedicine|article|814287|Cyanide Toxicity|treatment}}</ref>
An older cyanide antidote kit included administration of three substances: [[amyl nitrite]] pearls (administered by inhalation), [[sodium nitrite]], and [[sodium thiosulfate]]. The goal of the antidote was to generate a large pool of [[ferric]] iron ({{chem2|Fe(3+)}}) to compete for cyanide with cytochrome a<sub>3</sub> (so that cyanide will bind to the antidote rather than the enzyme). The [[nitrite]]s [[oxidize]] [[hemoglobin]] to [[methemoglobin]], which competes with cytochrome oxidase for the cyanide ion. Cyanmethemoglobin is formed and the [[cytochrome oxidase]] enzyme is restored. The major mechanism to remove the cyanide from the body is by enzymatic conversion to [[thiocyanate]] by the [[mitochondrial]] enzyme [[rhodanese]]. Thiocyanate is a relatively non-toxic molecule and is excreted by the kidneys. To accelerate this detoxification, sodium thiosulfate is administered to provide a sulfur donor for [[rhodanese]], needed in order to produce thiocyanate.<ref>{{cite journal | last1 = Chaudhary | first1 = M. | last2 = Gupta | first2 = R. | year = 2012 | title = Cyanide Detoxifying Enzyme: Rhodanese | journal = Current Biotechnology | volume = 1 | issue = 4 | pages = 327–335 | doi = 10.2174/2211550111201040327 }}</ref>
===Sensitivity===
Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, [[asthma]], or [[bronchitis]]. MRLs may be revised after sufficient data accumulates.<ref>{{cite report|title=Toxicological Profile for Cyanide |publisher=U.S. Department of Health and Human Services |date=2006 |url=https://www.atsdr.cdc.gov/toxprofiles/tp8.pdf |archive-url=https://web.archive.org/web/20040331014808/http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf |archive-date=2004-03-31 |url-status=live |pages=18–19}}</ref>
==Applications==
===Mining===
{{Main|Gold cyanidation}}
Cyanide is mainly produced for the [[mining]] of [[silver]] and [[gold]]: It helps dissolve these metals allowing separation from the other solids. In the ''[[cyanide process]]'', finely ground high-grade ore is mixed with the cyanide (at a ratio of about 1:500 parts NaCN to ore); low-grade ores are stacked into heaps and sprayed with a cyanide solution (at a ratio of about 1:1000 parts NaCN to ore). The precious metals are complexed by the cyanide [[anion]]s to form soluble derivatives, e.g., {{chem2|[Ag(CN)2]-}} (dicyanoargentate(I)) and {{chem2|[Au(CN)2]-}} (dicyanoaurate(I)).<ref name=Ullmann>{{Ullmann |first1=Andreas |last1=Rubo |first2=Raf |last2=Kellens |first3=Jay |last3=Reddy |first4=Norbert |last4=Steier |first5=Wolfgang |last5=Hasenpusch |title=Alkali Metal Cyanides |year=2006 |doi=10.1002/14356007.i01_i01}}</ref> Silver is less [[Noble metal|"noble"]] than gold and often occurs as the sulfide, in which case redox is not invoked (no {{chem2|O2}} is required). Instead, a displacement reaction occurs:
:<chem>Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH</chem>
:<chem>4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH</chem>
The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a [[tailing pond]] or spent heap, the recoverable gold having been removed. The metal is recovered from the "pregnant solution" by reduction with [[zinc]] dust or by [[adsorption]] onto [[activated carbon]]. This process can result in environmental and health problems. A number of [[List of gold mining disasters|environmental disasters]] have followed the overflow of tailing ponds at gold mines. Cyanide contamination of waterways has resulted in numerous cases of human and aquatic species mortality.<ref>{{cite journal |last1=Kumar |first1=Rahul |last2=Saha |first2=Shouvik |last3=Sarita |first3=Dhaka |last4=Mayur B. |first4=Kurade |last5=Kang |first5=Chan Ung |last6=Baek |first6=Seung Han |last7=Jeong |first7=Byong-Hun |title=Remediation of cyanide-contaminated environments through microbes and plants: a review of current knowledge and future perspectives |journal=Geosystem Engineering |date=2016 |volume=70 |issue=1 |pages=28–40 |doi=10.1080/12269328.2016.1218303 |s2cid=132571397 |url=https://www.tandfonline.com/doi/full/10.1080/12269328.2016.1218303 |access-date=24 April 2022}}</ref>
Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to [[iron pyrite]] (fool's gold), wherein half of the sulfur atoms are replaced by [[arsenic]]. Gold-containing arsenopyrite ores are similarly reactive toward inorganic cyanide.{{citation needed|date=July 2015}}
===Industrial organic chemistry===
The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles. [[Acyl cyanide]]s are produced from acyl chlorides and cyanide. [[Cyanogen]], [[cyanogen chloride]], and the trimer [[cyanuric chloride]] are derived from alkali metal cyanides.
===Medical uses===
The cyanide compound [[sodium nitroprusside]] is used mainly in [[clinical chemistry]] to measure [[urine]] [[ketone bodies]] mainly as a follow-up to [[diabetic]] patients. On occasion, it is used in emergency medical situations to produce a rapid decrease in [[blood pressure]] in humans; it is also used as a [[vasodilator]] in vascular research. The cobalt in artificial [[Vitamin B12|vitamin B<sub>12</sub>]] contains a cyanide ligand as an artifact of the purification process; this must be removed by the body before the vitamin molecule can be activated for biochemical use. During [[World War I]], a copper cyanide compound was briefly used by [[Japan]]ese physicians for the treatment of [[tuberculosis]] and [[leprosy]].<ref>{{Cite journal|last=Takano |first=R. |date=August 1916 |title=The treatment of leprosy with cyanocuprol |journal=The Journal of Experimental Medicine |volume=24 |issue= 2|pages=207–211 |url=http://www.jem.org/cgi/content/abstract/24/2/207 |access-date=2008-06-28 |doi=10.1084/jem.24.2.207 |pmc=2125457 |pmid=19868035}}</ref>
===Illegal fishing and poaching===
{{Main|Cyanide fishing}}
Cyanides are illegally used to capture live fish near [[coral reef]]s for the [[aquarium]] and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.<ref name="crc">Dzombak, David A; Ghosh, Rajat S; Wong-Chong, George M. ''Cyanide in Water and Soil''. [[CRC Press]], 2006, Chapter 11.2: "Use of Cyanide for Capturing Live Reef Fish".</ref>
Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.<ref>[http://www.abc.net.au/news/2013-09-25/zimbabwe-poachers-kill-80-elephants-with-cyanide/4981372 Poachers kill 80 elephants with cyanide in Zimbabwe] ''ABC News'', 25 September 2013. Retrieved 30 October 2015.</ref>
===Pest control===
[[M44 (cyanide device)|M44 cyanide devices]] are used in the United States to kill [[coyote]]s and other canids.<ref>{{cite journal|doi=10.1002/wsb.361|title=Animal attendance at M-44 sodium cyanide ejector sites for coyotes|journal=Wildlife Society Bulletin|volume=38|pages=217–220|year=2014|last1=Shivik|first1=John A.|last2=Mastro|first2=Lauren|last3=Young|first3=Julie K. |issue=1 |bibcode=2014WSBu...38..217S |url=http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=2419&context=icwdm_usdanwrc}}</ref> Cyanide is also used for pest control in [[New Zealand]], particularly for [[Common Brushtail Possum in New Zealand|possums]], an [[Invasive species in New Zealand|introduced marsupial that threatens the conservation of native species]] and spreads [[tuberculosis]] amongst cattle. Possums can become bait shy but the use of pellets containing the cyanide reduces bait shyness. Cyanide has been known to kill native birds, including the endangered [[Kiwi (bird)|kiwi]].<ref>{{cite web |last = Green| first = Wren |title =The use of 1080 for pest control |publisher = New Zealand Department of Conservation |date = July 2004 |url =http://www.doc.govt.nz/upload/documents/conservation/threats-and-impacts/animal-pests/use-of-1080-04.pdf| access-date = 8 June 2011}}</ref> Cyanide is also effective for controlling the [[dama wallaby]], another introduced marsupial pest in New Zealand.<ref>{{cite journal|last=Shapiro|first=Lee|date=21 March 2011|title=Effectiveness of cyanide pellets for control of dama wallabies (Macropus eugenii)|journal=New Zealand Journal of Ecology |volume=35 |issue=3 |url=http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf |archive-url=https://web.archive.org/web/20150203010818/http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf |archive-date=2015-02-03 |url-status=live |display-authors=etal}}</ref> A licence is required to store, handle and use cyanide in New Zealand.
Cyanides are used as [[insecticide]]s for fumigating ships.<ref>{{cite web|title=Sodium Cyanide|url=https://pubchem.ncbi.nlm.nih.gov/compound/sodium_cyanide|website=PubChem|publisher=National Center for Biotechnology Information|access-date=2 September 2016|date=2016|quote=Cyanide and hydrogen cyanide are used in electroplating, metallurgy, organic chemicals production, photographic developing, manufacture of plastics, fumigation of ships, and some mining processes.}}</ref> Cyanide salts are used for killing ants,<ref name="EPAReg1994">{{cite web|title=Reregistration Eligibility Decision (RED) Sodium Cyanide|url=https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf |archive-url=https://ghostarchive.org/archive/20221010/https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf |archive-date=2022-10-10 |url-status=live|website=EPA.gov|access-date=2 September 2016|page=7|date=1 September 1994|quote=Sodium cyanide was initially registered as a pesticide on December 23, 1947, to control ants on uncultivated agricultural and non-agricultural areas.}}</ref> and have in some places been used as rat poison<ref name="TariffInfo1921">{{cite web|title=Tariff Information, 1921: Hearings on General Tariff Revision Before the Committee on Ways and Means, House of Representatives|url=http://www.abebooks.com/servlet/SearchResults?tn=Tariff+Information,+1921|website=AbeBooks.com|publisher=US Congress, House Committee on Ways and Means, US Government Printing Office|access-date=2 September 2016|page=3987|date=1921|quote=Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin – especially in the fight against typhus.}}</ref> (the less toxic poison [[arsenic]] is more common).<ref name="PlanetDeadly2013">{{cite web|title=Deadliest Poisons Used by Man|url=http://www.planetdeadly.com/human/deadliest-poisons-man|website=PlanetDeadly.com|access-date=2 September 2016|archive-url=https://web.archive.org/web/20160511033535/http://www.planetdeadly.com/human/deadliest-poisons-man|archive-date=11 May 2016|date=18 November 2013}}</ref>
===Niche uses===
[[Potassium ferrocyanide]] is used to achieve a blue color on cast [[bronze sculpture]]s during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry.
Cyanide is also used in [[jewelry]]-making and certain kinds of [[photography]] such as [[sepia toning]].
Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.<ref>{{Cite journal|doi=10.1104/pp.52.1.23 |last1=Taylorson |first1=R. |last2=Hendricks |year=1973 |first2=SB |title=Promotion of Seed Germination by Cyanide |journal=Plant Physiol. |volume=52 |issue=1 |pages=23–27 |pmid=16658492 |pmc=366431}}</ref><ref>{{Cite journal|last1=Mullick |first1=P. |year=1967 |last2=Chatterji |first2=U. N. |title=Effect of sodium cyanide on germination of two leguminous seeds |journal=Plant Systematics and Evolution |volume=114 |pages=88–91|doi=10.1007/BF01373937|s2cid=2533762 }}</ref>
====Human poisoning====
{{main|Cyanide poisoning}}
Deliberate cyanide poisoning of humans has occurred many times throughout history.<ref>{{Cite book
|title=Medical Management of Chemical Casualties Handbook
|edition=4th
|last1=Bernan
|publisher=Government Printing Off
|year=2008
|isbn=978-0-16-081320-7
|page=41
|url=https://books.google.com/books?id=oiw2ZzsBvsoC}}, [https://books.google.com/books?id=oiw2ZzsBvsoC&pg=PA41 Extract p. 41]
</ref>
Common salts such as [[sodium cyanide]] are involatile but water-soluble, so are poisonous by ingestion. [[Hydrogen cyanide]] is a gas, making it more indiscriminately dangerous, however it is lighter than air and rapidly disperses up into the atmosphere, which makes it ineffective as a [[chemical weapon]]. Poisoning by hydrogen cyanide is more effective in an enclosed space, such as a [[gas chamber]]. Most significantly, hydrogen cyanide released from pellets of [[Zyklon-B]] was used extensively in the [[extermination camp]]s of [[the Holocaust]].
====Food additive====
Because of the high stability of their complexation with [[iron]], ferrocyanides ([[Sodium ferrocyanide]] E535, [[Potassium ferrocyanide]] E536, and Calcium ferrocyanide E538<ref>{{cite book
|title=Benders' dictionary of nutrition and food technology
|edition=7th
|first1=David A.
|last1=Bender
|first2=Arnold Eric
|last2=Bender
|publisher=Woodhead Publishing
|year=1997
|isbn=978-1-85573-475-3
|page=459
|url=https://books.google.com/books?id=IrYfDEl7XPYC}} [https://books.google.com/books?id=IrYfDEl7XPYC&pg=PA459 Extract of page 459]
</ref>) do not decompose to lethal levels in the human body and are used in the food industry as, e.g., an [[anticaking agent]] in [[table salt]].<ref>{{cite book
|title=Geochemical processes in soil and groundwater: measurement – modelling – upscaling
|first1=Horst D.
|last1=Schulz
|first2=Astrid
|last2=Hadeler
|author3=Deutsche Forschungsgemeinschaft
|publisher=Wiley-VCH
|year=2003
|isbn=978-3-527-27766-7
|page=67
|doi=10.1002/9783527609703
|url=http://onlinelibrary.wiley.com/doi/10.1002/9783527609703}}
</ref>
==Chemical tests for cyanide==
Cyanide is quantified by [[potentiometric titration]], a method widely used in gold mining. It can also be determined by titration with silver ion.
Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.<ref>{{Ullmann|doi=10.1002/14356007.a08_159.pub2|title=Cyano Compounds, Inorganic|year=2004|last1=Gail|first1=Ernst|last2=Gos|first2=Stephen|last3=Kulzer|first3=Rupprecht|last4=Lorösch|first4=Jürgen|last5=Rubo|first5=Andreas|last6=Sauer|first6=Manfred}}</ref>
===Qualitative tests===
Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of [[ferricyanide]].<ref>{{Ullmann |author1=Schwenecke, H. |author2=Mayer, D. | title = Benzidine and Benzidine Derivatives | year = 2005 | doi = 10.1002/14356007.a03_539 }}</ref> [[Iron(II) sulfate]] added to a solution of cyanide, such as the filtrate from the [[sodium fusion test]], gives [[prussian blue]]. A solution of [[1,4-Benzoquinone|''para''-benzoquinone]] in [[dimethyl sulfoxide|DMSO]] reacts with inorganic cyanide to form a cyano[[phenol]], which is [[fluorescent]]. Illumination with a [[UV light]] gives a green/blue glow if the test is positive.<ref>{{Cite journal| doi = 10.1016/0041-008X(80)90225-2 |pmid = 7423496 |title = Fluorometric determination of cyanide in biological fluids with p-benzoquinone*1 |first4 = JL |last4 = Way |first3 = RL |last3 = Morgan |first2 = GE |year = 1980 |last2 = Isom |last1 = Ganjeloo |first1 = A |journal = [[Toxicology and Applied Pharmacology]] |volume = 55 |issue = 1 |pages = 103–107 }}</ref>
==References==
{{Reflist}}
==External links==
{{EB1911 Poster|Cyanide}}
{{Commons category|Cyanides}}
*[https://web.archive.org/web/20100528070140/http://www.atsdr.cdc.gov/MMG/MMG.asp?id=1073&tid=19 ATSDR medical management guidelines for cyanide poisoning (US)]
*[http://www.hse.gov.uk/pubns/firindex.htm HSE recommendations for first aid treatment of cyanide poisoning (UK)]
*[http://www.inchem.org/documents/cicads/cicads/cicad61.htm Hydrogen cyanide and cyanides] ([[CICAD]] 61)
*[http://www.inchem.org/documents/antidote/antidote/ant02.htm#SubSectionNumber:1.13.1 IPCS/CEC Evaluation of antidotes for poisoning by cyanides]
*[https://web.archive.org/web/20060517035532/http://www.npi.gov.au/database/substance-info/profiles/29.html National Pollutant Inventory – Cyanide compounds fact sheet]
*[http://www.snopes.com/food/warnings/apples.asp#add Eating apple seeds is safe despite the small amount of cyanide]
*[http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, July 2006]
;Safety data (French)
* Institut national de recherche et de sécurité (1997). "[https://web.archive.org/web/20060220084315/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf Cyanure d'hydrogène et solutions aqueuses]". ''Fiche toxicologique n° 4'', Paris: INRS, 5 pp. (PDF file, {{in lang|fr}})
* Institut national de recherche et de sécurité (1997). "[https://web.archive.org/web/20060220084330/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/48145297F4EF18BBC1256CE8005A9FC2/$File/ft111.pdf Cyanure de sodium. Cyanure de potassium]". ''Fiche toxicologique n° 111'', Paris: INRS, 6 pp. (PDF file, {{in lang|fr}})
{{Cyanides}}
{{Inorganic compounds of carbon}}
{{Nitrogen compounds}}
{{Rodenticides}}
{{Consumer Food Safety}}
{{Authority control}}
[[Category:Cyanides]]
[[Category:Anions]]
[[Category:Blood agents]]
[[Category:Nitrogen(−III) compounds]]
[[Category:Toxicology]]' |
New page wikitext, after the edit (new_wikitext ) | '{{short description|Any molecule with a cyano group (–C≡N)}}
{{About|the class of chemical compounds}}
Cyanide is good
Good cyanide
[[Organic compound|Organic]] cyanides are usually called [[nitrile]]s. In nitriles, the {{chem2|\sC\tN}} group is linked by a single [[covalent bond]] to carbon. For example, in [[acetonitrile]] ({{chem2|CH3\sC\tN}}), the cyanide group is bonded to [[methyl]] ({{chem2|\sCH3}}). Although nitriles generally do not release cyanide ions, the [[cyanohydrin]]s do and are thus toxic.
==Bonding==
The cyanide ion {{chem2|−C\tN}} is [[isoelectronic]] with [[carbon monoxide]] {{chem2|-C\tO+}} and with molecular [[nitrogen]] N≡N. A triple bond exists between C and N. The negative charge is concentrated on [[carbon]] C.<ref>Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. {{ISBN|0-7506-3365-4}}.{{page needed|date=July 2015}}</ref><ref>G. L. Miessler and D. A. Tarr "Inorganic Chemistry" 3rd Ed, Pearson/Prentice Hall publisher, {{ISBN|0-13-035471-6}}.{{page needed|date=July 2015}}</ref>
==Occurrence==
===In nature===
[[File:Removal of cyanide poison from cassava.jpg|thumb|left|Removal of cyanide from [[cassava]] in [[Nigeria]].]]
Cyanides are produced by certain [[bacterium|bacteria]], [[fungi]], and [[algae]]. It is an [[antifeedant]] in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of [[bitter almond]]s, [[apricot]]s, [[apple]]s, and [[peach]]es.<ref>{{Cite web|url=https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=71&tid=19 |title=ToxFAQs for Cyanide |access-date=2008-06-28 |date = July 2006|publisher=[[Agency for Toxic Substances and Disease Registry]]}}</ref> Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to [[sugar]] molecules in the form of cyanogenic [[glycoside]]s and defend the plant against [[herbivore]]s. [[Cassava]] roots (also called manioc), an important [[potato]]-like food grown in tropical countries (and the base from which [[tapioca]] is made), also contain cyanogenic glycosides.<ref>{{Cite journal|first=J. |last=Vetter |title=Plant cyanogenic glycosides |journal=Toxicon |year=2000 |volume=38 |pages=11–36 |doi=10.1016/S0041-0101(99)00128-2 |pmid=10669009 |issue=1}}</ref><ref name=jones>{{Cite journal|first=D. A. |last=Jones |title= Why are so many food plants cyanogenic? |journal=[[Phytochemistry (journal)|Phytochemistry]] |year=1998 |volume=47 |pages=155–162 |doi=10.1016/S0031-9422(97)00425-1 |pmid=9431670 |issue=2|bibcode=1998PChem..47..155J }}</ref>
The [[Madagascar]] bamboo ''[[Cathariostachys madagascariensis]]'' produces cyanide as a deterrent to grazing. In response, the [[golden bamboo lemur]], which eats the bamboo, has developed a high tolerance to cyanide.
The [[hydrogenase]] enzymes contain cyanide [[ligand]]s attached to iron in their active sites. The biosynthesis of cyanide in the [[NiFe hydrogenase]]s proceeds from [[carbamoyl phosphate]], which converts to [[cystein]]yl [[thiocyanate]], the {{chem2|CN−}} donor.<ref>{{cite journal |last1=Reissmann |first1=Stefanie |last2=Hochleitner |first2=Elisabeth |last3=Wang |first3=Haofan |last4=Paschos |first4=Athanasios |last5=Lottspeich |first5=Friedrich |last6=Glass |first6=Richard S. |last7=Böck |first7=August |title=Taming of a Poison: Biosynthesis of the NiFe-Hydrogenase Cyanide Ligands |journal=Science |volume=299 |issue=5609 |pages=1067–1070 |year=2003 |pmid=12586941 |doi=10.1126/science.1080972 |bibcode=2003Sci...299.1067R |s2cid=20488694 |url=http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf |archive-url=https://web.archive.org/web/20201123134841/http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf |archive-date=2020-11-23 |url-status=live }}</ref>
===Interstellar medium===
The [[cyanide radical]] <sup>•</sup>CN has been identified in [[interstellar space]].<ref>{{Cite journal |last=Pieniazek |first=Piotr A. |author2=Bradforth, Stephen E. |author3=Krylov, Anna I. |title=Spectroscopy of the Cyano Radical in an Aqueous Environment |date=2005-12-07 |pages=4854–4865 |issue=14 |volume=110 |url=http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf |journal=The Journal of Physical Chemistry A |pmid=16599455 |doi=10.1021/jp0545952 |bibcode=2006JPCA..110.4854P |access-date=2008-08-23 |archive-url=https://web.archive.org/web/20080911131555/http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf |archive-date=2008-09-11 |url-status=dead }}</ref> [[Cyanogen]], {{chem2|(CN)2}}, is used to measure the temperature of [[Molecular cloud|interstellar gas clouds]].<ref>{{cite journal |title = Interstellar Cyanogen and the Temperature of the Cosmic Microwave Background Radiation |author1=Roth, K. C. |author2=Meyer, D. M. |author3=Hawkins, I.|author3-link=Isabel Hawkins |journal = The Astrophysical Journal |year = 1993 |volume = 413 |issue = 2 |pages = L67–L71 |doi = 10.1086/186961 |bibcode = 1993ApJ...413L..67R |url = http://articles.adsabs.harvard.edu/cgi-bin/nph-iarticle_query?1993ApJ...413L..67R&data_type=PDF_HIGH&whole_paper=YES&type=PRINTER&filetype=.pdf }}</ref>
===Pyrolysis and combustion product===
Hydrogen cyanide is produced by the combustion or [[pyrolysis]] of certain materials under oxygen-deficient conditions. For example, it can be detected in the [[exhaust gas|exhaust]] of [[internal combustion engine]]s and [[tobacco]] smoke. Certain [[plastic]]s, especially those derived from [[acrylonitrile]], release hydrogen cyanide when heated or burnt.<ref name="CDC"/>
===Organic derivatives===
{{Main|Nitriles}}
{{see also|Isocyanide}}
In [[IUPAC nomenclature of organic chemistry|IUPAC nomenclature]], [[organic compound]]s that have a {{chem2|\sC\tN}} [[functional group]] are called [[nitrile]]s.<ref>[[IUPAC Gold Book]] [http://goldbook.iupac.org/N04151.html ''nitriles'']</ref><ref>NCBI-MeSH [https://www.ncbi.nlm.nih.gov/mesh/68009570 ''Nitriles'']</ref> An example of a nitrile is [[acetonitrile]], {{chem2|CH3\sC\tN}}. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl {{chem2|\sOH}} and cyanide {{chem2|\sCN}} bonded to the same carbon atom is called [[cyanohydrin]] ({{chem2|R2C(OH)CN}}). Unlike nitriles, cyanohydrins do release poisonous [[hydrogen cyanide]].
==Reactions==
===Protonation===
Cyanide is basic. The p''K''<sub>a</sub> of hydrogen cyanide is 9.21. Thus, addition of [[acids]] stronger than hydrogen cyanide to solutions of cyanide salts releases [[hydrogen cyanide]].
===Hydrolysis===
Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes [[hydrolysis]] to give [[ammonia]] and [[formate]], which are far less toxic than cyanide:<ref name=Ullmann/>
:{{chem2|CN- + 2 H2O → HCO2- + NH3}}
[[Cyanide hydrolase]] is an [[enzyme]] that catalyzes this reaction.
===Alkylation===
Because of the cyanide anion's high [[nucleophile|nucleophilicity]], cyano groups are readily introduced into organic molecules by displacement of a [[halide]] group (e.g., the [[chloride]] on [[methyl chloride]]). In general, organic cyanides are called nitriles. In organic synthesis, cyanide is a C-1 [[synthon]]; i.e., it can be used to lengthen a carbon chain by one, while retaining the ability to be [[wiktionary:functionalize|functionalized]].<ref>{{Ullmann|doi=10.1002/14356007.a17_363|title=Nitriles|year=2000|last1=Pollak|first1=Peter|last2=Romeder|first2=Gérard|last3=Hagedorn|first3=Ferdinand|last4=Gelbke|first4=Heinz-Peter|isbn=3-527-30673-0}}</ref>
:{{chem2|RX + CN- → RCN + X-}}
===Redox===
The cyanide ion is a [[reducing agent|reductant]] and is [[oxidation|oxidized]] by strong [[oxidizing agent]]s such as molecular [[chlorine]] ({{chem2|Cl2}}), [[hypochlorite]] ({{chem2|ClO-}}), and [[hydrogen peroxide]] ({{chem2|H2O2}}). These oxidizers are used to destroy cyanides in [[effluent]]s from [[gold mining]].<ref name="Young_1995">Young, C. A., & Jordan, T. S. (1995, May). Cyanide remediation: current and past technologies. In: Proceedings of the 10th Annual Conference on Hazardous Waste Research (pp. 104–129). Kansas State University: Manhattan, KS. https://engg.ksu.edu/HSRC/95Proceed/young.pdf</ref><ref name="SRK">{{Cite web |title=Cyanide Destruction {{!}} SRK Consulting |author=Dmitry Yermakov |work=srk.com |date= |access-date=2 March 2021 |url= https://www.srk.com/en/publications/cyanide-destruction |language=English}}</ref><ref name="Botz">Botz Michael M. Overview of cyanide treatment methods. Elbow Creek Engineering, Inc. http://www.botz.com/MEMCyanideTreatment.pdf</ref>
===Metal complexation===
The cyanide anion reacts with [[transition metals]] to form [[Cyanometalate|M-CN bonds]]. This reaction is the basis of cyanide's toxicity.<ref>Sharpe, A. G. The Chemistry of Cyano Complexes of the Transition Metals; Academic Press: London, 1976{{page needed|date=July 2015}}</ref> The high affinities of metals for this [[anion]] can be attributed to its negative charge, compactness, and ability to engage in π-bonding.
Among the most important cyanide coordination compounds are the [[potassium ferrocyanide]] and the pigment [[Prussian blue]], which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.<ref name=Holl>{{ cite book |author1=Holleman, A. F. |author2=Wiberg, E. | title = Inorganic Chemistry | publisher = Academic Press | location = San Diego | year = 2001 | isbn = 978-0-12-352651-9 }}</ref>
Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to [[blueprints]], [[bluing (fabric)|bluing]], and [[cyanotype]]s.
==Manufacture==
{{main|Hydrogen cyanide#Production and synthesis}}
The principal process used to manufacture cyanides is the [[Andrussow process]] in which gaseous [[hydrogen cyanide]] is produced from [[methane]] and [[ammonia]] in the presence of [[oxygen]] and a [[platinum]] [[catalyst]].<ref>{{cite journal
|title=Über die schnell verlaufenden katalytischen Prozesse in strömenden Gasen und die Ammoniak-Oxydation (V) |trans-title=About the quicka catalytic processes in flowing gases and the ammonia oxidation (V) |language=de |author-link1=Leonid Andrussow |first1=Leonid |last1=Andrussow |journal=Berichte der Deutschen Chemischen Gesellschaft |volume=60 |issue=8 |pages=2005–2018 |year=1927 |doi=10.1002/cber.19270600857 }}</ref><ref>{{cite journal |title=Über die katalytische Oxydation von Ammoniak-Methan-Gemischen zu Blausäure |trans-title=About the catalytic oxidation of ammonia-methane mixtures to cyanide |language=de |first1=L. |last1=Andrussow |journal=[[Angewandte Chemie]] |volume=48 |issue=37 |pages=593–595 |year=1935 |doi=10.1002/ange.19350483702 |bibcode=1935AngCh..48..593A }}</ref>
:{{chem2|2 CH4 + 2 NH3 + 3 O2 → 2 HCN + 6 H2O}}
Sodium cyanide, the precursor to most cyanides, is produced by treating [[hydrogen cyanide]] with [[sodium hydroxide]]:<ref name=Ullmann />
:{{chem2|HCN + NaOH → NaCN + H2O}}
==Toxicity==
{{Main|Cyanide poisoning}}
Many cyanides are highly toxic. The cyanide anion is an [[enzyme inhibitor|inhibitor]] of the [[enzyme]] [[cytochrome c oxidase]] (also known as aa<sub>3</sub>), the fourth complex of the [[electron transport chain]] found in the [[Inner mitochondrial membrane|inner membrane]] of the [[mitochondria]] of [[Eukaryote|eukaryotic]] cells. It attaches to the iron within this protein. The binding of cyanide to this enzyme prevents transport of electrons from [[cytochrome c]] to oxygen. As a result, the electron transport chain is disrupted, meaning that the cell can no longer aerobically produce [[adenosine triphosphate|ATP]] for energy.<ref>{{cite book|last1=Nelson|first1=David L.|last2=Cox|first2=Michael M.|title=Lehniger Principles of Biochemistry|publisher=[[Worth Publishers]]|year=2000|location=New York|edition=3rd|isbn=978-1-57259-153-0|pages=[https://archive.org/details/lehningerprincip01lehn/page/668 668,670–71,676]|url=https://archive.org/details/lehningerprincip01lehn/page/668}}</ref> Tissues that depend highly on [[aerobic respiration]], such as the [[central nervous system]] and the [[heart]], are particularly affected. This is an example of [[histotoxic hypoxia]].<ref name=Biller>{{cite book
|title=Interface of neurology and internal medicine
|edition=illustrated
|first1=José
|last1=Biller
|publisher=Lippincott Williams & Wilkins
|year=2007
|isbn=978-0-7817-7906-7
|chapter=163
|page=939
|chapter-url=https://books.google.com/books?id=SRIvmTVcYBwC&pg=PA939}}
</ref>
The most hazardous compound is [[hydrogen cyanide]], which is a gas and kills by inhalation. For this reason, an air respirator supplied by an external oxygen source must be worn when working with hydrogen cyanide.<ref name="CDC">{{Cite web|url=https://emergency.cdc.gov/agent/cyanide/basics/facts.asp|title=Facts about cyanide:Where cyanide is found and how it is used|last=Anon|date=June 27, 2013|work=CDC Emergency preparedness and response|publisher=Centers for Disease Control and Prevention|access-date=10 December 2016}}</ref> Hydrogen cyanide is produced by adding acid to a solution containing a cyanide salt. Alkaline solutions of cyanide are safer to use because they do not evolve hydrogen cyanide gas. Hydrogen cyanide may be produced in the combustion of [[polyurethane]]s; for this reason, polyurethanes are not recommended for use in domestic and aircraft furniture. Oral ingestion of a small quantity of solid cyanide or a cyanide solution of as little as 200 mg, or exposure to airborne cyanide of 270 [[parts per million|ppm]], is sufficient to cause death within minutes.<ref name=Biller/>
Organic [[nitrile]]s do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as [[trimethylsilyl cyanide]] {{chem2|(CH3)3SiCN}} readily release HCN or the cyanide ion upon contact with water.<ref>{{cite web |url=https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf |archive-url=https://ghostarchive.org/archive/20221010/https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf |archive-date=2022-10-10 |url-status=live |title=MSDS of trimethylsilyl cyanide |publisher=Gelest Inc |date=2008 |access-date=2022-08-16}}</ref>
===Antidote===
[[Hydroxocobalamin]] reacts with cyanide to form [[cyanocobalamin]], which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.<ref>{{EMedicine|article|814287|Cyanide Toxicity|treatment}}</ref>
An older cyanide antidote kit included administration of three substances: [[amyl nitrite]] pearls (administered by inhalation), [[sodium nitrite]], and [[sodium thiosulfate]]. The goal of the antidote was to generate a large pool of [[ferric]] iron ({{chem2|Fe(3+)}}) to compete for cyanide with cytochrome a<sub>3</sub> (so that cyanide will bind to the antidote rather than the enzyme). The [[nitrite]]s [[oxidize]] [[hemoglobin]] to [[methemoglobin]], which competes with cytochrome oxidase for the cyanide ion. Cyanmethemoglobin is formed and the [[cytochrome oxidase]] enzyme is restored. The major mechanism to remove the cyanide from the body is by enzymatic conversion to [[thiocyanate]] by the [[mitochondrial]] enzyme [[rhodanese]]. Thiocyanate is a relatively non-toxic molecule and is excreted by the kidneys. To accelerate this detoxification, sodium thiosulfate is administered to provide a sulfur donor for [[rhodanese]], needed in order to produce thiocyanate.<ref>{{cite journal | last1 = Chaudhary | first1 = M. | last2 = Gupta | first2 = R. | year = 2012 | title = Cyanide Detoxifying Enzyme: Rhodanese | journal = Current Biotechnology | volume = 1 | issue = 4 | pages = 327–335 | doi = 10.2174/2211550111201040327 }}</ref>
===Sensitivity===
Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, [[asthma]], or [[bronchitis]]. MRLs may be revised after sufficient data accumulates.<ref>{{cite report|title=Toxicological Profile for Cyanide |publisher=U.S. Department of Health and Human Services |date=2006 |url=https://www.atsdr.cdc.gov/toxprofiles/tp8.pdf |archive-url=https://web.archive.org/web/20040331014808/http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf |archive-date=2004-03-31 |url-status=live |pages=18–19}}</ref>
==Applications==
===Mining===
{{Main|Gold cyanidation}}
Cyanide is mainly produced for the [[mining]] of [[silver]] and [[gold]]: It helps dissolve these metals allowing separation from the other solids. In the ''[[cyanide process]]'', finely ground high-grade ore is mixed with the cyanide (at a ratio of about 1:500 parts NaCN to ore); low-grade ores are stacked into heaps and sprayed with a cyanide solution (at a ratio of about 1:1000 parts NaCN to ore). The precious metals are complexed by the cyanide [[anion]]s to form soluble derivatives, e.g., {{chem2|[Ag(CN)2]-}} (dicyanoargentate(I)) and {{chem2|[Au(CN)2]-}} (dicyanoaurate(I)).<ref name=Ullmann>{{Ullmann |first1=Andreas |last1=Rubo |first2=Raf |last2=Kellens |first3=Jay |last3=Reddy |first4=Norbert |last4=Steier |first5=Wolfgang |last5=Hasenpusch |title=Alkali Metal Cyanides |year=2006 |doi=10.1002/14356007.i01_i01}}</ref> Silver is less [[Noble metal|"noble"]] than gold and often occurs as the sulfide, in which case redox is not invoked (no {{chem2|O2}} is required). Instead, a displacement reaction occurs:
:<chem>Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH</chem>
:<chem>4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH</chem>
The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a [[tailing pond]] or spent heap, the recoverable gold having been removed. The metal is recovered from the "pregnant solution" by reduction with [[zinc]] dust or by [[adsorption]] onto [[activated carbon]]. This process can result in environmental and health problems. A number of [[List of gold mining disasters|environmental disasters]] have followed the overflow of tailing ponds at gold mines. Cyanide contamination of waterways has resulted in numerous cases of human and aquatic species mortality.<ref>{{cite journal |last1=Kumar |first1=Rahul |last2=Saha |first2=Shouvik |last3=Sarita |first3=Dhaka |last4=Mayur B. |first4=Kurade |last5=Kang |first5=Chan Ung |last6=Baek |first6=Seung Han |last7=Jeong |first7=Byong-Hun |title=Remediation of cyanide-contaminated environments through microbes and plants: a review of current knowledge and future perspectives |journal=Geosystem Engineering |date=2016 |volume=70 |issue=1 |pages=28–40 |doi=10.1080/12269328.2016.1218303 |s2cid=132571397 |url=https://www.tandfonline.com/doi/full/10.1080/12269328.2016.1218303 |access-date=24 April 2022}}</ref>
Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to [[iron pyrite]] (fool's gold), wherein half of the sulfur atoms are replaced by [[arsenic]]. Gold-containing arsenopyrite ores are similarly reactive toward inorganic cyanide.{{citation needed|date=July 2015}}
===Industrial organic chemistry===
The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles. [[Acyl cyanide]]s are produced from acyl chlorides and cyanide. [[Cyanogen]], [[cyanogen chloride]], and the trimer [[cyanuric chloride]] are derived from alkali metal cyanides.
===Medical uses===
The cyanide compound [[sodium nitroprusside]] is used mainly in [[clinical chemistry]] to measure [[urine]] [[ketone bodies]] mainly as a follow-up to [[diabetic]] patients. On occasion, it is used in emergency medical situations to produce a rapid decrease in [[blood pressure]] in humans; it is also used as a [[vasodilator]] in vascular research. The cobalt in artificial [[Vitamin B12|vitamin B<sub>12</sub>]] contains a cyanide ligand as an artifact of the purification process; this must be removed by the body before the vitamin molecule can be activated for biochemical use. During [[World War I]], a copper cyanide compound was briefly used by [[Japan]]ese physicians for the treatment of [[tuberculosis]] and [[leprosy]].<ref>{{Cite journal|last=Takano |first=R. |date=August 1916 |title=The treatment of leprosy with cyanocuprol |journal=The Journal of Experimental Medicine |volume=24 |issue= 2|pages=207–211 |url=http://www.jem.org/cgi/content/abstract/24/2/207 |access-date=2008-06-28 |doi=10.1084/jem.24.2.207 |pmc=2125457 |pmid=19868035}}</ref>
===Illegal fishing and poaching===
{{Main|Cyanide fishing}}
Cyanides are illegally used to capture live fish near [[coral reef]]s for the [[aquarium]] and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.<ref name="crc">Dzombak, David A; Ghosh, Rajat S; Wong-Chong, George M. ''Cyanide in Water and Soil''. [[CRC Press]], 2006, Chapter 11.2: "Use of Cyanide for Capturing Live Reef Fish".</ref>
Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.<ref>[http://www.abc.net.au/news/2013-09-25/zimbabwe-poachers-kill-80-elephants-with-cyanide/4981372 Poachers kill 80 elephants with cyanide in Zimbabwe] ''ABC News'', 25 September 2013. Retrieved 30 October 2015.</ref>
===Pest control===
[[M44 (cyanide device)|M44 cyanide devices]] are used in the United States to kill [[coyote]]s and other canids.<ref>{{cite journal|doi=10.1002/wsb.361|title=Animal attendance at M-44 sodium cyanide ejector sites for coyotes|journal=Wildlife Society Bulletin|volume=38|pages=217–220|year=2014|last1=Shivik|first1=John A.|last2=Mastro|first2=Lauren|last3=Young|first3=Julie K. |issue=1 |bibcode=2014WSBu...38..217S |url=http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=2419&context=icwdm_usdanwrc}}</ref> Cyanide is also used for pest control in [[New Zealand]], particularly for [[Common Brushtail Possum in New Zealand|possums]], an [[Invasive species in New Zealand|introduced marsupial that threatens the conservation of native species]] and spreads [[tuberculosis]] amongst cattle. Possums can become bait shy but the use of pellets containing the cyanide reduces bait shyness. Cyanide has been known to kill native birds, including the endangered [[Kiwi (bird)|kiwi]].<ref>{{cite web |last = Green| first = Wren |title =The use of 1080 for pest control |publisher = New Zealand Department of Conservation |date = July 2004 |url =http://www.doc.govt.nz/upload/documents/conservation/threats-and-impacts/animal-pests/use-of-1080-04.pdf| access-date = 8 June 2011}}</ref> Cyanide is also effective for controlling the [[dama wallaby]], another introduced marsupial pest in New Zealand.<ref>{{cite journal|last=Shapiro|first=Lee|date=21 March 2011|title=Effectiveness of cyanide pellets for control of dama wallabies (Macropus eugenii)|journal=New Zealand Journal of Ecology |volume=35 |issue=3 |url=http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf |archive-url=https://web.archive.org/web/20150203010818/http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf |archive-date=2015-02-03 |url-status=live |display-authors=etal}}</ref> A licence is required to store, handle and use cyanide in New Zealand.
Cyanides are used as [[insecticide]]s for fumigating ships.<ref>{{cite web|title=Sodium Cyanide|url=https://pubchem.ncbi.nlm.nih.gov/compound/sodium_cyanide|website=PubChem|publisher=National Center for Biotechnology Information|access-date=2 September 2016|date=2016|quote=Cyanide and hydrogen cyanide are used in electroplating, metallurgy, organic chemicals production, photographic developing, manufacture of plastics, fumigation of ships, and some mining processes.}}</ref> Cyanide salts are used for killing ants,<ref name="EPAReg1994">{{cite web|title=Reregistration Eligibility Decision (RED) Sodium Cyanide|url=https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf |archive-url=https://ghostarchive.org/archive/20221010/https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf |archive-date=2022-10-10 |url-status=live|website=EPA.gov|access-date=2 September 2016|page=7|date=1 September 1994|quote=Sodium cyanide was initially registered as a pesticide on December 23, 1947, to control ants on uncultivated agricultural and non-agricultural areas.}}</ref> and have in some places been used as rat poison<ref name="TariffInfo1921">{{cite web|title=Tariff Information, 1921: Hearings on General Tariff Revision Before the Committee on Ways and Means, House of Representatives|url=http://www.abebooks.com/servlet/SearchResults?tn=Tariff+Information,+1921|website=AbeBooks.com|publisher=US Congress, House Committee on Ways and Means, US Government Printing Office|access-date=2 September 2016|page=3987|date=1921|quote=Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin – especially in the fight against typhus.}}</ref> (the less toxic poison [[arsenic]] is more common).<ref name="PlanetDeadly2013">{{cite web|title=Deadliest Poisons Used by Man|url=http://www.planetdeadly.com/human/deadliest-poisons-man|website=PlanetDeadly.com|access-date=2 September 2016|archive-url=https://web.archive.org/web/20160511033535/http://www.planetdeadly.com/human/deadliest-poisons-man|archive-date=11 May 2016|date=18 November 2013}}</ref>
===Niche uses===
[[Potassium ferrocyanide]] is used to achieve a blue color on cast [[bronze sculpture]]s during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry.
Cyanide is also used in [[jewelry]]-making and certain kinds of [[photography]] such as [[sepia toning]].
Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.<ref>{{Cite journal|doi=10.1104/pp.52.1.23 |last1=Taylorson |first1=R. |last2=Hendricks |year=1973 |first2=SB |title=Promotion of Seed Germination by Cyanide |journal=Plant Physiol. |volume=52 |issue=1 |pages=23–27 |pmid=16658492 |pmc=366431}}</ref><ref>{{Cite journal|last1=Mullick |first1=P. |year=1967 |last2=Chatterji |first2=U. N. |title=Effect of sodium cyanide on germination of two leguminous seeds |journal=Plant Systematics and Evolution |volume=114 |pages=88–91|doi=10.1007/BF01373937|s2cid=2533762 }}</ref>
====Human poisoning====
{{main|Cyanide poisoning}}
Deliberate cyanide poisoning of humans has occurred many times throughout history.<ref>{{Cite book
|title=Medical Management of Chemical Casualties Handbook
|edition=4th
|last1=Bernan
|publisher=Government Printing Off
|year=2008
|isbn=978-0-16-081320-7
|page=41
|url=https://books.google.com/books?id=oiw2ZzsBvsoC}}, [https://books.google.com/books?id=oiw2ZzsBvsoC&pg=PA41 Extract p. 41]
</ref>
Common salts such as [[sodium cyanide]] are involatile but water-soluble, so are poisonous by ingestion. [[Hydrogen cyanide]] is a gas, making it more indiscriminately dangerous, however it is lighter than air and rapidly disperses up into the atmosphere, which makes it ineffective as a [[chemical weapon]]. Poisoning by hydrogen cyanide is more effective in an enclosed space, such as a [[gas chamber]]. Most significantly, hydrogen cyanide released from pellets of [[Zyklon-B]] was used extensively in the [[extermination camp]]s of [[the Holocaust]].
====Food additive====
Because of the high stability of their complexation with [[iron]], ferrocyanides ([[Sodium ferrocyanide]] E535, [[Potassium ferrocyanide]] E536, and Calcium ferrocyanide E538<ref>{{cite book
|title=Benders' dictionary of nutrition and food technology
|edition=7th
|first1=David A.
|last1=Bender
|first2=Arnold Eric
|last2=Bender
|publisher=Woodhead Publishing
|year=1997
|isbn=978-1-85573-475-3
|page=459
|url=https://books.google.com/books?id=IrYfDEl7XPYC}} [https://books.google.com/books?id=IrYfDEl7XPYC&pg=PA459 Extract of page 459]
</ref>) do not decompose to lethal levels in the human body and are used in the food industry as, e.g., an [[anticaking agent]] in [[table salt]].<ref>{{cite book
|title=Geochemical processes in soil and groundwater: measurement – modelling – upscaling
|first1=Horst D.
|last1=Schulz
|first2=Astrid
|last2=Hadeler
|author3=Deutsche Forschungsgemeinschaft
|publisher=Wiley-VCH
|year=2003
|isbn=978-3-527-27766-7
|page=67
|doi=10.1002/9783527609703
|url=http://onlinelibrary.wiley.com/doi/10.1002/9783527609703}}
</ref>
==Chemical tests for cyanide==
Cyanide is quantified by [[potentiometric titration]], a method widely used in gold mining. It can also be determined by titration with silver ion.
Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.<ref>{{Ullmann|doi=10.1002/14356007.a08_159.pub2|title=Cyano Compounds, Inorganic|year=2004|last1=Gail|first1=Ernst|last2=Gos|first2=Stephen|last3=Kulzer|first3=Rupprecht|last4=Lorösch|first4=Jürgen|last5=Rubo|first5=Andreas|last6=Sauer|first6=Manfred}}</ref>
===Qualitative tests===
Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of [[ferricyanide]].<ref>{{Ullmann |author1=Schwenecke, H. |author2=Mayer, D. | title = Benzidine and Benzidine Derivatives | year = 2005 | doi = 10.1002/14356007.a03_539 }}</ref> [[Iron(II) sulfate]] added to a solution of cyanide, such as the filtrate from the [[sodium fusion test]], gives [[prussian blue]]. A solution of [[1,4-Benzoquinone|''para''-benzoquinone]] in [[dimethyl sulfoxide|DMSO]] reacts with inorganic cyanide to form a cyano[[phenol]], which is [[fluorescent]]. Illumination with a [[UV light]] gives a green/blue glow if the test is positive.<ref>{{Cite journal| doi = 10.1016/0041-008X(80)90225-2 |pmid = 7423496 |title = Fluorometric determination of cyanide in biological fluids with p-benzoquinone*1 |first4 = JL |last4 = Way |first3 = RL |last3 = Morgan |first2 = GE |year = 1980 |last2 = Isom |last1 = Ganjeloo |first1 = A |journal = [[Toxicology and Applied Pharmacology]] |volume = 55 |issue = 1 |pages = 103–107 }}</ref>
==References==
{{Reflist}}
==External links==
{{EB1911 Poster|Cyanide}}
{{Commons category|Cyanides}}
*[https://web.archive.org/web/20100528070140/http://www.atsdr.cdc.gov/MMG/MMG.asp?id=1073&tid=19 ATSDR medical management guidelines for cyanide poisoning (US)]
*[http://www.hse.gov.uk/pubns/firindex.htm HSE recommendations for first aid treatment of cyanide poisoning (UK)]
*[http://www.inchem.org/documents/cicads/cicads/cicad61.htm Hydrogen cyanide and cyanides] ([[CICAD]] 61)
*[http://www.inchem.org/documents/antidote/antidote/ant02.htm#SubSectionNumber:1.13.1 IPCS/CEC Evaluation of antidotes for poisoning by cyanides]
*[https://web.archive.org/web/20060517035532/http://www.npi.gov.au/database/substance-info/profiles/29.html National Pollutant Inventory – Cyanide compounds fact sheet]
*[http://www.snopes.com/food/warnings/apples.asp#add Eating apple seeds is safe despite the small amount of cyanide]
*[http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, July 2006]
;Safety data (French)
* Institut national de recherche et de sécurité (1997). "[https://web.archive.org/web/20060220084315/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf Cyanure d'hydrogène et solutions aqueuses]". ''Fiche toxicologique n° 4'', Paris: INRS, 5 pp. (PDF file, {{in lang|fr}})
* Institut national de recherche et de sécurité (1997). "[https://web.archive.org/web/20060220084330/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/48145297F4EF18BBC1256CE8005A9FC2/$File/ft111.pdf Cyanure de sodium. Cyanure de potassium]". ''Fiche toxicologique n° 111'', Paris: INRS, 6 pp. (PDF file, {{in lang|fr}})
{{Cyanides}}
{{Inorganic compounds of carbon}}
{{Nitrogen compounds}}
{{Rodenticides}}
{{Consumer Food Safety}}
{{Authority control}}
[[Category:Cyanides]]
[[Category:Anions]]
[[Category:Blood agents]]
[[Category:Nitrogen(−III) compounds]]
[[Category:Toxicology]]' |
Unified diff of changes made by edit (edit_diff ) | '@@ -1,39 +1,7 @@
{{short description|Any molecule with a cyano group (–C≡N)}}
{{About|the class of chemical compounds}}
-{{distinguish|Nitrile}}
-{{Chembox
-| ImageFile = Cyanide-montage.png
-| ImageAlt = Space-filling model of the cyanide anion: carbon bound to smaller nitrogen atom
-| Name=Cyanide anion
-| PIN = Cyanide
-| SystematicName = Nitridocarbonate(II)
-| IUPACName =
-| OtherNames =
-|Section1 = {{Chembox Identifiers
-| CASNo = 57-12-5
-| UNII_Ref = {{fdacite|correct|FDA}}
-| UNII = OXN4E7L11K
-| PubChem = 5975
-| ChEBI = 17514
-| SMILES = [C-]#N
-| ChemSpiderID = 5755
-| InChI = 1S/CN/c1-2/q-1
-| InChIKey = XFXPMWWXUTWYJX-UHFFFAOYSA-N
-}}
-|Section2 = {{Chembox Properties
-| Formula = {{chem2|CN−}}
-| C=1|N=1
-| Appearance =
-| Solubility =
-| ConjugateAcid = [[Hydrogen cyanide]]}}
-|Section3 = {{Chembox Hazards
-| MainHazards = The cyanide ion {{chem2|CN−}} is one of the most poisonous chemicals. It may cause death in minutes.
-| FlashPt =
-| AutoignitionPt = }}
-}}
+Cyanide is good
-In [[chemistry]], '''cyanide''' ({{ety|el|kyanos|[[Prussian blue|dark blue]]}}) is a [[chemical compound]] that contains a {{chem2|C\tN}} [[functional group]]. This group, known as the '''cyano group''', consists of a [[carbon]] atom [[triple-bond]]ed to a [[nitrogen]] atom.<ref>{{cite journal|url=http://goldbook.iupac.org/C01486.html |title=cyanides|website=[[IUPAC Gold Book]] |date=2014 |doi=10.1351/goldbook.C01486 |doi-access=free }}</ref>
-
-In [[Inorganic compound|inorganic]] cyanides, the cyanide group is present as the cyanide anion {{chem2|−C\tN}}. This anion is [[Cyanide poisoning|extremely poisonous]]. Soluble [[Salt (chemistry)|salts]] such as [[sodium cyanide]] (NaCN) and [[potassium cyanide]] (KCN) are highly toxic.<ref name="CMC">{{Cite web| url=http://www.cyanidecode.org/cyanide_environmental.php| title=Environmental and Health Effects of Cyanide| publisher=International Cyanide Management Institute| year=2006| access-date=4 August 2009| archive-date=30 November 2012| archive-url=https://web.archive.org/web/20121130094124/http://www.cyanidecode.org/cyanide_environmental.php| url-status=dead}}</ref> [[Hydrocyanic acid]], also known as hydrogen cyanide, or HCN, is a highly [[Volatility (chemistry)|volatile]] liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.
+Good cyanide
[[Organic compound|Organic]] cyanides are usually called [[nitrile]]s. In nitriles, the {{chem2|\sC\tN}} group is linked by a single [[covalent bond]] to carbon. For example, in [[acetonitrile]] ({{chem2|CH3\sC\tN}}), the cyanide group is bonded to [[methyl]] ({{chem2|\sCH3}}). Although nitriles generally do not release cyanide ions, the [[cyanohydrin]]s do and are thus toxic.
' |
New page size (new_size ) | 32965 |
Old page size (old_size ) | 35128 |
Size change in edit (edit_delta ) | -2163 |
Lines added in edit (added_lines ) | [
0 => 'Cyanide is good',
1 => 'Good cyanide'
] |
Lines removed in edit (removed_lines ) | [
0 => '{{distinguish|Nitrile}}',
1 => '{{Chembox',
2 => '| ImageFile = Cyanide-montage.png',
3 => '| ImageAlt = Space-filling model of the cyanide anion: carbon bound to smaller nitrogen atom',
4 => '| Name=Cyanide anion',
5 => '| PIN = Cyanide',
6 => '| SystematicName = Nitridocarbonate(II)',
7 => '| IUPACName =',
8 => '| OtherNames =',
9 => '|Section1 = {{Chembox Identifiers',
10 => '| CASNo = 57-12-5',
11 => '| UNII_Ref = {{fdacite|correct|FDA}}',
12 => '| UNII = OXN4E7L11K',
13 => '| PubChem = 5975',
14 => '| ChEBI = 17514',
15 => '| SMILES = [C-]#N',
16 => '| ChemSpiderID = 5755',
17 => '| InChI = 1S/CN/c1-2/q-1',
18 => '| InChIKey = XFXPMWWXUTWYJX-UHFFFAOYSA-N',
19 => '}}',
20 => '|Section2 = {{Chembox Properties',
21 => '| Formula = {{chem2|CN−}}',
22 => '| C=1|N=1',
23 => '| Appearance =',
24 => '| Solubility =',
25 => '| ConjugateAcid = [[Hydrogen cyanide]]}}',
26 => '|Section3 = {{Chembox Hazards',
27 => '| MainHazards = The cyanide ion {{chem2|CN−}} is one of the most poisonous chemicals. It may cause death in minutes.',
28 => '| FlashPt =',
29 => '| AutoignitionPt = }}',
30 => '}}',
31 => 'In [[chemistry]], '''cyanide''' ({{ety|el|kyanos|[[Prussian blue|dark blue]]}}) is a [[chemical compound]] that contains a {{chem2|C\tN}} [[functional group]]. This group, known as the '''cyano group''', consists of a [[carbon]] atom [[triple-bond]]ed to a [[nitrogen]] atom.<ref>{{cite journal|url=http://goldbook.iupac.org/C01486.html |title=cyanides|website=[[IUPAC Gold Book]] |date=2014 |doi=10.1351/goldbook.C01486 |doi-access=free }}</ref>',
32 => '',
33 => 'In [[Inorganic compound|inorganic]] cyanides, the cyanide group is present as the cyanide anion {{chem2|−C\tN}}. This anion is [[Cyanide poisoning|extremely poisonous]]. Soluble [[Salt (chemistry)|salts]] such as [[sodium cyanide]] (NaCN) and [[potassium cyanide]] (KCN) are highly toxic.<ref name="CMC">{{Cite web| url=http://www.cyanidecode.org/cyanide_environmental.php| title=Environmental and Health Effects of Cyanide| publisher=International Cyanide Management Institute| year=2006| access-date=4 August 2009| archive-date=30 November 2012| archive-url=https://web.archive.org/web/20121130094124/http://www.cyanidecode.org/cyanide_environmental.php| url-status=dead}}</ref> [[Hydrocyanic acid]], also known as hydrogen cyanide, or HCN, is a highly [[Volatility (chemistry)|volatile]] liquid that is produced on a large scale industrially. It is obtained by acidification of cyanide salts.'
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Parsed HTML source of the new revision (new_html ) | '<div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Any molecule with a cyano group (–C≡N)</div>
<style data-mw-deduplicate="TemplateStyles:r1033289096">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the class of chemical compounds. For other uses, see <a href="/wiki/Cyanide_(disambiguation)" class="mw-disambig" title="Cyanide (disambiguation)">Cyanide (disambiguation)</a>.</div>
<p>Cyanide is good
</p><p>Good cyanide
</p><p><a href="/wiki/Organic_compound" title="Organic compound">Organic</a> cyanides are usually called <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>. In nitriles, the <style data-mw-deduplicate="TemplateStyles:r1123817410">.mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-align:-0.35em}.mw-parser-output .template-chem2-su>span{display:block;text-align:left}.mw-parser-output sub.template-chem2-sub{font-size:80%;vertical-align:-0.35em}.mw-parser-output sup.template-chem2-sup{font-size:80%;vertical-align:0.65em}</style><span class="chemf nowrap">−C≡N</span> group is linked by a single <a href="/wiki/Covalent_bond" title="Covalent bond">covalent bond</a> to carbon. For example, in <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C≡N</span>), the cyanide group is bonded to <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CH<sub class="template-chem2-sub">3</sub></span>). Although nitriles generally do not release cyanide ions, the <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrins</a> do and are thus toxic.
</p>
<div id="toc" class="toc" role="navigation" aria-labelledby="mw-toc-heading"><input type="checkbox" role="button" id="toctogglecheckbox" class="toctogglecheckbox" style="display:none" /><div class="toctitle" lang="en" dir="ltr"><h2 id="mw-toc-heading">Contents</h2><span class="toctogglespan"><label class="toctogglelabel" for="toctogglecheckbox"></label></span></div>
<ul>
<li class="toclevel-1 tocsection-1"><a href="#Bonding"><span class="tocnumber">1</span> <span class="toctext">Bonding</span></a></li>
<li class="toclevel-1 tocsection-2"><a href="#Occurrence"><span class="tocnumber">2</span> <span class="toctext">Occurrence</span></a>
<ul>
<li class="toclevel-2 tocsection-3"><a href="#In_nature"><span class="tocnumber">2.1</span> <span class="toctext">In nature</span></a></li>
<li class="toclevel-2 tocsection-4"><a href="#Interstellar_medium"><span class="tocnumber">2.2</span> <span class="toctext">Interstellar medium</span></a></li>
<li class="toclevel-2 tocsection-5"><a href="#Pyrolysis_and_combustion_product"><span class="tocnumber">2.3</span> <span class="toctext">Pyrolysis and combustion product</span></a></li>
<li class="toclevel-2 tocsection-6"><a href="#Organic_derivatives"><span class="tocnumber">2.4</span> <span class="toctext">Organic derivatives</span></a></li>
</ul>
</li>
<li class="toclevel-1 tocsection-7"><a href="#Reactions"><span class="tocnumber">3</span> <span class="toctext">Reactions</span></a>
<ul>
<li class="toclevel-2 tocsection-8"><a href="#Protonation"><span class="tocnumber">3.1</span> <span class="toctext">Protonation</span></a></li>
<li class="toclevel-2 tocsection-9"><a href="#Hydrolysis"><span class="tocnumber">3.2</span> <span class="toctext">Hydrolysis</span></a></li>
<li class="toclevel-2 tocsection-10"><a href="#Alkylation"><span class="tocnumber">3.3</span> <span class="toctext">Alkylation</span></a></li>
<li class="toclevel-2 tocsection-11"><a href="#Redox"><span class="tocnumber">3.4</span> <span class="toctext">Redox</span></a></li>
<li class="toclevel-2 tocsection-12"><a href="#Metal_complexation"><span class="tocnumber">3.5</span> <span class="toctext">Metal complexation</span></a></li>
</ul>
</li>
<li class="toclevel-1 tocsection-13"><a href="#Manufacture"><span class="tocnumber">4</span> <span class="toctext">Manufacture</span></a></li>
<li class="toclevel-1 tocsection-14"><a href="#Toxicity"><span class="tocnumber">5</span> <span class="toctext">Toxicity</span></a>
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<li class="toclevel-2 tocsection-15"><a href="#Antidote"><span class="tocnumber">5.1</span> <span class="toctext">Antidote</span></a></li>
<li class="toclevel-2 tocsection-16"><a href="#Sensitivity"><span class="tocnumber">5.2</span> <span class="toctext">Sensitivity</span></a></li>
</ul>
</li>
<li class="toclevel-1 tocsection-17"><a href="#Applications"><span class="tocnumber">6</span> <span class="toctext">Applications</span></a>
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<li class="toclevel-2 tocsection-18"><a href="#Mining"><span class="tocnumber">6.1</span> <span class="toctext">Mining</span></a></li>
<li class="toclevel-2 tocsection-19"><a href="#Industrial_organic_chemistry"><span class="tocnumber">6.2</span> <span class="toctext">Industrial organic chemistry</span></a></li>
<li class="toclevel-2 tocsection-20"><a href="#Medical_uses"><span class="tocnumber">6.3</span> <span class="toctext">Medical uses</span></a></li>
<li class="toclevel-2 tocsection-21"><a href="#Illegal_fishing_and_poaching"><span class="tocnumber">6.4</span> <span class="toctext">Illegal fishing and poaching</span></a></li>
<li class="toclevel-2 tocsection-22"><a href="#Pest_control"><span class="tocnumber">6.5</span> <span class="toctext">Pest control</span></a></li>
<li class="toclevel-2 tocsection-23"><a href="#Niche_uses"><span class="tocnumber">6.6</span> <span class="toctext">Niche uses</span></a>
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<li class="toclevel-3 tocsection-24"><a href="#Human_poisoning"><span class="tocnumber">6.6.1</span> <span class="toctext">Human poisoning</span></a></li>
<li class="toclevel-3 tocsection-25"><a href="#Food_additive"><span class="tocnumber">6.6.2</span> <span class="toctext">Food additive</span></a></li>
</ul>
</li>
</ul>
</li>
<li class="toclevel-1 tocsection-26"><a href="#Chemical_tests_for_cyanide"><span class="tocnumber">7</span> <span class="toctext">Chemical tests for cyanide</span></a>
<ul>
<li class="toclevel-2 tocsection-27"><a href="#Qualitative_tests"><span class="tocnumber">7.1</span> <span class="toctext">Qualitative tests</span></a></li>
</ul>
</li>
<li class="toclevel-1 tocsection-28"><a href="#References"><span class="tocnumber">8</span> <span class="toctext">References</span></a></li>
<li class="toclevel-1 tocsection-29"><a href="#External_links"><span class="tocnumber">9</span> <span class="toctext">External links</span></a></li>
</ul>
</div>
<div class="mw-heading mw-heading2"><h2 id="Bonding">Bonding</h2><span class="mw-editsection">
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<p>The cyanide ion <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><sup class="template-chem2-sup">−</sup>C≡N</span> is <a href="/wiki/Isoelectronic" class="mw-redirect" title="Isoelectronic">isoelectronic</a> with <a href="/wiki/Carbon_monoxide" title="Carbon monoxide">carbon monoxide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap"><sup class="template-chem2-sup">−</sup>C≡O<sup class="template-chem2-sup">+</sup></span> and with molecular <a href="/wiki/Nitrogen" title="Nitrogen">nitrogen</a> N≡N. A triple bond exists between C and N. The negative charge is concentrated on <a href="/wiki/Carbon" title="Carbon">carbon</a> C.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1">[1]</a></sup><sup id="cite_ref-2" class="reference"><a href="#cite_note-2">[2]</a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Occurrence">Occurrence</h2><span class="mw-editsection">
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<div class="mw-heading mw-heading3"><h3 id="In_nature">In nature</h3><span class="mw-editsection">
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<figure class="mw-default-size mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Removal_of_cyanide_poison_from_cassava.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/220px-Removal_of_cyanide_poison_from_cassava.jpg" decoding="async" width="220" height="148" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/330px-Removal_of_cyanide_poison_from_cassava.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/1b/Removal_of_cyanide_poison_from_cassava.jpg/440px-Removal_of_cyanide_poison_from_cassava.jpg 2x" data-file-width="2896" data-file-height="1944" /></a><figcaption>Removal of cyanide from <a href="/wiki/Cassava" title="Cassava">cassava</a> in <a href="/wiki/Nigeria" title="Nigeria">Nigeria</a>.</figcaption></figure>
<p>Cyanides are produced by certain <a href="/wiki/Bacterium" class="mw-redirect" title="Bacterium">bacteria</a>, <a href="/wiki/Fungi" class="mw-redirect" title="Fungi">fungi</a>, and <a href="/wiki/Algae" title="Algae">algae</a>. It is an <a href="/wiki/Antifeedant" title="Antifeedant">antifeedant</a> in a number of plants. Cyanides are found in substantial amounts in certain seeds and fruit stones, e.g., those of <a href="/wiki/Bitter_almond" class="mw-redirect" title="Bitter almond">bitter almonds</a>, <a href="/wiki/Apricot" title="Apricot">apricots</a>, <a href="/wiki/Apple" title="Apple">apples</a>, and <a href="/wiki/Peach" title="Peach">peaches</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3">[3]</a></sup> Chemical compounds that can release cyanide are known as cyanogenic compounds. In plants, cyanides are usually bound to <a href="/wiki/Sugar" title="Sugar">sugar</a> molecules in the form of cyanogenic <a href="/wiki/Glycoside" title="Glycoside">glycosides</a> and defend the plant against <a href="/wiki/Herbivore" title="Herbivore">herbivores</a>. <a href="/wiki/Cassava" title="Cassava">Cassava</a> roots (also called manioc), an important <a href="/wiki/Potato" title="Potato">potato</a>-like food grown in tropical countries (and the base from which <a href="/wiki/Tapioca" title="Tapioca">tapioca</a> is made), also contain cyanogenic glycosides.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4">[4]</a></sup><sup id="cite_ref-jones_5-0" class="reference"><a href="#cite_note-jones-5">[5]</a></sup>
</p><p>The <a href="/wiki/Madagascar" title="Madagascar">Madagascar</a> bamboo <i><a href="/wiki/Cathariostachys_madagascariensis" title="Cathariostachys madagascariensis">Cathariostachys madagascariensis</a></i> produces cyanide as a deterrent to grazing. In response, the <a href="/wiki/Golden_bamboo_lemur" title="Golden bamboo lemur">golden bamboo lemur</a>, which eats the bamboo, has developed a high tolerance to cyanide.
</p><p>The <a href="/wiki/Hydrogenase" title="Hydrogenase">hydrogenase</a> enzymes contain cyanide <a href="/wiki/Ligand" title="Ligand">ligands</a> attached to iron in their active sites. The biosynthesis of cyanide in the <a href="/wiki/NiFe_hydrogenase" title="NiFe hydrogenase">NiFe hydrogenases</a> proceeds from <a href="/wiki/Carbamoyl_phosphate" title="Carbamoyl phosphate">carbamoyl phosphate</a>, which converts to <a href="/wiki/Cystein" class="mw-redirect" title="Cystein">cysteinyl</a> <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a>, the <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup></span> donor.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6">[6]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Interstellar_medium">Interstellar medium</h3><span class="mw-editsection">
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<p>The <a href="/wiki/Cyanide_radical" class="mw-redirect" title="Cyanide radical">cyanide radical</a> <sup>•</sup>CN has been identified in <a href="/wiki/Interstellar_space" class="mw-redirect" title="Interstellar space">interstellar space</a>.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7">[7]</a></sup> <a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CN)<sub class="template-chem2-sub">2</sub></span>, is used to measure the temperature of <a href="/wiki/Molecular_cloud" title="Molecular cloud">interstellar gas clouds</a>.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8">[8]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Pyrolysis_and_combustion_product">Pyrolysis and combustion product</h3><span class="mw-editsection">
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<p>Hydrogen cyanide is produced by the combustion or <a href="/wiki/Pyrolysis" title="Pyrolysis">pyrolysis</a> of certain materials under oxygen-deficient conditions. For example, it can be detected in the <a href="/wiki/Exhaust_gas" title="Exhaust gas">exhaust</a> of <a href="/wiki/Internal_combustion_engine" title="Internal combustion engine">internal combustion engines</a> and <a href="/wiki/Tobacco" title="Tobacco">tobacco</a> smoke. Certain <a href="/wiki/Plastic" title="Plastic">plastics</a>, especially those derived from <a href="/wiki/Acrylonitrile" title="Acrylonitrile">acrylonitrile</a>, release hydrogen cyanide when heated or burnt.<sup id="cite_ref-CDC_9-0" class="reference"><a href="#cite_note-CDC-9">[9]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Organic_derivatives">Organic derivatives</h3><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Nitriles" class="mw-redirect" title="Nitriles">Nitriles</a></div>
<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Isocyanide" title="Isocyanide">Isocyanide</a></div>
<p>In <a href="/wiki/IUPAC_nomenclature_of_organic_chemistry" title="IUPAC nomenclature of organic chemistry">IUPAC nomenclature</a>, <a href="/wiki/Organic_compound" title="Organic compound">organic compounds</a> that have a <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−C≡N</span> <a href="/wiki/Functional_group" title="Functional group">functional group</a> are called <a href="/wiki/Nitrile" title="Nitrile">nitriles</a>.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10">[10]</a></sup><sup id="cite_ref-11" class="reference"><a href="#cite_note-11">[11]</a></sup> An example of a nitrile is <a href="/wiki/Acetonitrile" title="Acetonitrile">acetonitrile</a>, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CH<sub class="template-chem2-sub">3</sub>−C≡N</span>. Nitriles usually do not release cyanide ions. A functional group with a hydroxyl <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−OH</span> and cyanide <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">−CN</span> bonded to the same carbon atom is called <a href="/wiki/Cyanohydrin" title="Cyanohydrin">cyanohydrin</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">R<sub class="template-chem2-sub">2</sub>C(OH)CN</span>). Unlike nitriles, cyanohydrins do release poisonous <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>.
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<div class="mw-heading mw-heading2"><h2 id="Reactions">Reactions</h2><span class="mw-editsection">
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<div class="mw-heading mw-heading3"><h3 id="Protonation">Protonation</h3><span class="mw-editsection">
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<p>Cyanide is basic. The p<i>K</i><sub>a</sub> of hydrogen cyanide is 9.21. Thus, addition of <a href="/wiki/Acids" class="mw-redirect" title="Acids">acids</a> stronger than hydrogen cyanide to solutions of cyanide salts releases <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>.
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<div class="mw-heading mw-heading3"><h3 id="Hydrolysis">Hydrolysis</h3><span class="mw-editsection">
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<p>Cyanide is unstable in water, but the reaction is slow until about 170 °C. It undergoes <a href="/wiki/Hydrolysis" title="Hydrolysis">hydrolysis</a> to give <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> and <a href="/wiki/Formate" title="Formate">formate</a>, which are far less toxic than cyanide:<sup id="cite_ref-Ullmann_12-0" class="reference"><a href="#cite_note-Ullmann-12">[12]</a></sup>
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<dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">CN<sup class="template-chem2-sup">−</sup> + 2 H<sub class="template-chem2-sub">2</sub>O → HCO<span class="template-chem2-su"><span>−</span><span>2</span></span> + NH<sub class="template-chem2-sub">3</sub></span></dd></dl>
<p><a href="/w/index.php?title=Cyanide_hydrolase&action=edit&redlink=1" class="new" title="Cyanide hydrolase (page does not exist)">Cyanide hydrolase</a> is an <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> that catalyzes this reaction.
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<div class="mw-heading mw-heading3"><h3 id="Alkylation">Alkylation</h3><span class="mw-editsection">
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<p>Because of the cyanide anion's high <a href="/wiki/Nucleophile" title="Nucleophile">nucleophilicity</a>, cyano groups are readily introduced into organic molecules by displacement of a <a href="/wiki/Halide" title="Halide">halide</a> group (e.g., the <a href="/wiki/Chloride" title="Chloride">chloride</a> on <a href="/wiki/Methyl_chloride" class="mw-redirect" title="Methyl chloride">methyl chloride</a>). In general, organic cyanides are called nitriles. In organic synthesis, cyanide is a C-1 <a href="/wiki/Synthon" title="Synthon">synthon</a>; i.e., it can be used to lengthen a carbon chain by one, while retaining the ability to be <a href="https://en.wiktionary.org/wiki/functionalize" class="extiw" title="wiktionary:functionalize">functionalized</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13">[13]</a></sup>
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<dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">RX + CN<sup class="template-chem2-sup">−</sup> → RCN + X<sup class="template-chem2-sup">−</sup></span></dd></dl>
<div class="mw-heading mw-heading3"><h3 id="Redox">Redox</h3><span class="mw-editsection">
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<p>The cyanide ion is a <a href="/wiki/Reducing_agent" title="Reducing agent">reductant</a> and is <a href="/wiki/Oxidation" class="mw-redirect" title="Oxidation">oxidized</a> by strong <a href="/wiki/Oxidizing_agent" title="Oxidizing agent">oxidizing agents</a> such as molecular <a href="/wiki/Chlorine" title="Chlorine">chlorine</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cl<sub class="template-chem2-sub">2</sub></span>), <a href="/wiki/Hypochlorite" title="Hypochlorite">hypochlorite</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">ClO<sup class="template-chem2-sup">−</sup></span>), and <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">H<sub class="template-chem2-sub">2</sub>O<sub class="template-chem2-sub">2</sub></span>). These oxidizers are used to destroy cyanides in <a href="/wiki/Effluent" title="Effluent">effluents</a> from <a href="/wiki/Gold_mining" title="Gold mining">gold mining</a>.<sup id="cite_ref-Young_1995_14-0" class="reference"><a href="#cite_note-Young_1995-14">[14]</a></sup><sup id="cite_ref-SRK_15-0" class="reference"><a href="#cite_note-SRK-15">[15]</a></sup><sup id="cite_ref-Botz_16-0" class="reference"><a href="#cite_note-Botz-16">[16]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Metal_complexation">Metal complexation</h3><span class="mw-editsection">
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<p>The cyanide anion reacts with <a href="/wiki/Transition_metals" class="mw-redirect" title="Transition metals">transition metals</a> to form <a href="/wiki/Cyanometalate" title="Cyanometalate">M-CN bonds</a>. This reaction is the basis of cyanide's toxicity.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17">[17]</a></sup> The high affinities of metals for this <a href="/wiki/Anion" class="mw-redirect" title="Anion">anion</a> can be attributed to its negative charge, compactness, and ability to engage in π-bonding.
</p><p>Among the most important cyanide coordination compounds are the <a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">potassium ferrocyanide</a> and the pigment <a href="/wiki/Prussian_blue" title="Prussian blue">Prussian blue</a>, which are both essentially nontoxic due to the tight binding of the cyanides to a central iron atom.<sup id="cite_ref-Holl_18-0" class="reference"><a href="#cite_note-Holl-18">[18]</a></sup>
Prussian blue was first accidentally made around 1706, by heating substances containing iron and carbon and nitrogen, and other cyanides made subsequently (and named after it). Among its many uses, Prussian blue gives the blue color to <a href="/wiki/Blueprints" class="mw-redirect" title="Blueprints">blueprints</a>, <a href="/wiki/Bluing_(fabric)" title="Bluing (fabric)">bluing</a>, and <a href="/wiki/Cyanotype" title="Cyanotype">cyanotypes</a>.
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<div class="mw-heading mw-heading2"><h2 id="Manufacture">Manufacture</h2><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Hydrogen_cyanide#Production_and_synthesis" title="Hydrogen cyanide">Hydrogen cyanide § Production and synthesis</a></div>
<p>The principal process used to manufacture cyanides is the <a href="/wiki/Andrussow_process" title="Andrussow process">Andrussow process</a> in which gaseous <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> is produced from <a href="/wiki/Methane" title="Methane">methane</a> and <a href="/wiki/Ammonia" title="Ammonia">ammonia</a> in the presence of <a href="/wiki/Oxygen" title="Oxygen">oxygen</a> and a <a href="/wiki/Platinum" title="Platinum">platinum</a> <a href="/wiki/Catalyst" class="mw-redirect" title="Catalyst">catalyst</a>.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19">[19]</a></sup><sup id="cite_ref-20" class="reference"><a href="#cite_note-20">[20]</a></sup>
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<dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">2 CH<sub class="template-chem2-sub">4</sub> + 2 NH<sub class="template-chem2-sub">3</sub> + 3 O<sub class="template-chem2-sub">2</sub> → 2 HCN + 6 H<sub class="template-chem2-sub">2</sub>O</span></dd></dl>
<p>Sodium cyanide, the precursor to most cyanides, is produced by treating <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a> with <a href="/wiki/Sodium_hydroxide" title="Sodium hydroxide">sodium hydroxide</a>:<sup id="cite_ref-Ullmann_12-1" class="reference"><a href="#cite_note-Ullmann-12">[12]</a></sup>
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<dl><dd><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">HCN + NaOH → NaCN + H<sub class="template-chem2-sub">2</sub>O</span></dd></dl>
<div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</a></div>
<p>Many cyanides are highly toxic. The cyanide anion is an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of the <a href="/wiki/Enzyme" title="Enzyme">enzyme</a> <a href="/wiki/Cytochrome_c_oxidase" title="Cytochrome c oxidase">cytochrome c oxidase</a> (also known as aa<sub>3</sub>), the fourth complex of the <a href="/wiki/Electron_transport_chain" title="Electron transport chain">electron transport chain</a> found in the <a href="/wiki/Inner_mitochondrial_membrane" title="Inner mitochondrial membrane">inner membrane</a> of the <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a> of <a href="/wiki/Eukaryote" title="Eukaryote">eukaryotic</a> cells. It attaches to the iron within this protein. The binding of cyanide to this enzyme prevents transport of electrons from <a href="/wiki/Cytochrome_c" title="Cytochrome c">cytochrome c</a> to oxygen. As a result, the electron transport chain is disrupted, meaning that the cell can no longer aerobically produce <a href="/wiki/Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> for energy.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21">[21]</a></sup> Tissues that depend highly on <a href="/wiki/Aerobic_respiration" class="mw-redirect" title="Aerobic respiration">aerobic respiration</a>, such as the <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a> and the <a href="/wiki/Heart" title="Heart">heart</a>, are particularly affected. This is an example of <a href="/wiki/Histotoxic_hypoxia" title="Histotoxic hypoxia">histotoxic hypoxia</a>.<sup id="cite_ref-Biller_22-0" class="reference"><a href="#cite_note-Biller-22">[22]</a></sup>
</p><p>The most hazardous compound is <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">hydrogen cyanide</a>, which is a gas and kills by inhalation. For this reason, an air respirator supplied by an external oxygen source must be worn when working with hydrogen cyanide.<sup id="cite_ref-CDC_9-1" class="reference"><a href="#cite_note-CDC-9">[9]</a></sup> Hydrogen cyanide is produced by adding acid to a solution containing a cyanide salt. Alkaline solutions of cyanide are safer to use because they do not evolve hydrogen cyanide gas. Hydrogen cyanide may be produced in the combustion of <a href="/wiki/Polyurethane" title="Polyurethane">polyurethanes</a>; for this reason, polyurethanes are not recommended for use in domestic and aircraft furniture. Oral ingestion of a small quantity of solid cyanide or a cyanide solution of as little as 200 mg, or exposure to airborne cyanide of 270 <a href="/wiki/Parts_per_million" class="mw-redirect" title="Parts per million">ppm</a>, is sufficient to cause death within minutes.<sup id="cite_ref-Biller_22-1" class="reference"><a href="#cite_note-Biller-22">[22]</a></sup>
</p><p>Organic <a href="/wiki/Nitrile" title="Nitrile">nitriles</a> do not readily release cyanide ions, and so have low toxicities. By contrast, compounds such as <a href="/wiki/Trimethylsilyl_cyanide" title="Trimethylsilyl cyanide">trimethylsilyl cyanide</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>SiCN</span> readily release HCN or the cyanide ion upon contact with water.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23">[23]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Antidote">Antidote</h3><span class="mw-editsection">
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<p><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a> reacts with cyanide to form <a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">cyanocobalamin</a>, which can be safely eliminated by the kidneys. This method has the advantage of avoiding the formation of methemoglobin (see below). This antidote kit is sold under the brand name Cyanokit and was approved by the U.S. FDA in 2006.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24">[24]</a></sup>
</p><p>An older cyanide antidote kit included administration of three substances: <a href="/wiki/Amyl_nitrite" title="Amyl nitrite">amyl nitrite</a> pearls (administered by inhalation), <a href="/wiki/Sodium_nitrite" title="Sodium nitrite">sodium nitrite</a>, and <a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a>. The goal of the antidote was to generate a large pool of <a href="/wiki/Ferric" title="Ferric">ferric</a> iron (<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Fe<sup>3+</sup></span>) to compete for cyanide with cytochrome a<sub>3</sub> (so that cyanide will bind to the antidote rather than the enzyme). The <a href="/wiki/Nitrite" title="Nitrite">nitrites</a> <a href="/wiki/Oxidize" class="mw-redirect" title="Oxidize">oxidize</a> <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> to <a href="/wiki/Methemoglobin" title="Methemoglobin">methemoglobin</a>, which competes with cytochrome oxidase for the cyanide ion. Cyanmethemoglobin is formed and the <a href="/wiki/Cytochrome_oxidase" class="mw-redirect" title="Cytochrome oxidase">cytochrome oxidase</a> enzyme is restored. The major mechanism to remove the cyanide from the body is by enzymatic conversion to <a href="/wiki/Thiocyanate" title="Thiocyanate">thiocyanate</a> by the <a href="/wiki/Mitochondrial" class="mw-redirect" title="Mitochondrial">mitochondrial</a> enzyme <a href="/wiki/Rhodanese" title="Rhodanese">rhodanese</a>. Thiocyanate is a relatively non-toxic molecule and is excreted by the kidneys. To accelerate this detoxification, sodium thiosulfate is administered to provide a sulfur donor for <a href="/wiki/Rhodanese" title="Rhodanese">rhodanese</a>, needed in order to produce thiocyanate.<sup id="cite_ref-25" class="reference"><a href="#cite_note-25">[25]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Sensitivity">Sensitivity</h3><span class="mw-editsection">
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<p>Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, <a href="/wiki/Asthma" title="Asthma">asthma</a>, or <a href="/wiki/Bronchitis" title="Bronchitis">bronchitis</a>. MRLs may be revised after sufficient data accumulates.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26">[26]</a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection">
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<div class="mw-heading mw-heading3"><h3 id="Mining">Mining</h3><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Gold_cyanidation" title="Gold cyanidation">Gold cyanidation</a></div>
<p>Cyanide is mainly produced for the <a href="/wiki/Mining" title="Mining">mining</a> of <a href="/wiki/Silver" title="Silver">silver</a> and <a href="/wiki/Gold" title="Gold">gold</a>: It helps dissolve these metals allowing separation from the other solids. In the <i><a href="/wiki/Cyanide_process" class="mw-redirect" title="Cyanide process">cyanide process</a></i>, finely ground high-grade ore is mixed with the cyanide (at a ratio of about 1:500 parts NaCN to ore); low-grade ores are stacked into heaps and sprayed with a cyanide solution (at a ratio of about 1:1000 parts NaCN to ore). The precious metals are complexed by the cyanide <a href="/wiki/Anion" class="mw-redirect" title="Anion">anions</a> to form soluble derivatives, e.g., <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Ag(CN)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span> (dicyanoargentate(I)) and <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">[Au(CN)<sub class="template-chem2-sub">2</sub>]<sup class="template-chem2-sup">−</sup></span> (dicyanoaurate(I)).<sup id="cite_ref-Ullmann_12-2" class="reference"><a href="#cite_note-Ullmann-12">[12]</a></sup> Silver is less <a href="/wiki/Noble_metal" title="Noble metal">"noble"</a> than gold and often occurs as the sulfide, in which case redox is not invoked (no <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub></span> is required). Instead, a displacement reaction occurs:
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<dl><dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}">
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<mrow class="MJX-TeXAtom-ORD">
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<mtext>Ag</mtext>
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<mtext>S</mtext>
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<mtext>NaCN</mtext>
<mo>+</mo>
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<mtext>H</mtext>
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<mn>2</mn>
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<mtext>O</mtext>
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<mtext>Na</mtext>
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<mo stretchy="false">[</mo>
<mtext>Ag</mtext>
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<mo stretchy="false">(</mo>
<mtext>CN</mtext>
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</msubsup>
<mo stretchy="false">]</mo>
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<mtext>NaSH</mtext>
<mo>+</mo>
<mtext>NaOH</mtext>
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<annotation encoding="application/x-tex">{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}</annotation>
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</math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/fdb057d86c43d8885c7802a16b185d6927372a71" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:61.529ex; height:3.009ex;" alt="{\displaystyle {\ce {Ag2S + 4 NaCN + H2O -> 2 Na[Ag(CN)2] + NaSH + NaOH}}}"></span></dd>
<dd><span class="mwe-math-element"><span class="mwe-math-mathml-inline mwe-math-mathml-a11y" style="display: none;"><math xmlns="http://www.w3.org/1998/Math/MathML" alttext="{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}">
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<mtext>O</mtext>
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<annotation encoding="application/x-tex">{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}</annotation>
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</math></span><img src="https://wikimedia.org/api/rest_v1/media/math/render/svg/52060e78e1dcc4a241c0759c4d733887e658ce3b" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:61.012ex; height:3.009ex;" alt="{\displaystyle {\ce {4 Au + 8 NaCN + O2 + 2 H2O -> 4 Na[Au(CN)2] + 4 NaOH}}}"></span></dd></dl>
<p>The "pregnant liquor" containing these ions is separated from the solids, which are discarded to a <a href="/wiki/Tailing_pond" class="mw-redirect" title="Tailing pond">tailing pond</a> or spent heap, the recoverable gold having been removed. The metal is recovered from the "pregnant solution" by reduction with <a href="/wiki/Zinc" title="Zinc">zinc</a> dust or by <a href="/wiki/Adsorption" title="Adsorption">adsorption</a> onto <a href="/wiki/Activated_carbon" title="Activated carbon">activated carbon</a>. This process can result in environmental and health problems. A number of <a href="/wiki/List_of_gold_mining_disasters" title="List of gold mining disasters">environmental disasters</a> have followed the overflow of tailing ponds at gold mines. Cyanide contamination of waterways has resulted in numerous cases of human and aquatic species mortality.<sup id="cite_ref-27" class="reference"><a href="#cite_note-27">[27]</a></sup>
</p><p>Aqueous cyanide is hydrolyzed rapidly, especially in sunlight. It can mobilize some heavy metals such as mercury if present. Gold can also be associated with arsenopyrite (FeAsS), which is similar to <a href="/wiki/Iron_pyrite" class="mw-redirect" title="Iron pyrite">iron pyrite</a> (fool's gold), wherein half of the sulfur atoms are replaced by <a href="/wiki/Arsenic" title="Arsenic">arsenic</a>. Gold-containing arsenopyrite ores are similarly reactive toward inorganic cyanide.<sup class="noprint Inline-Template Template-Fact" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed"><span title="This claim needs references to reliable sources. (July 2015)">citation needed</span></a></i>]</sup>
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<div class="mw-heading mw-heading3"><h3 id="Industrial_organic_chemistry">Industrial organic chemistry</h3><span class="mw-editsection">
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<p>The second major application of alkali metal cyanides (after mining) is in the production of CN-containing compounds, usually nitriles. <a href="/wiki/Acyl_cyanide" title="Acyl cyanide">Acyl cyanides</a> are produced from acyl chlorides and cyanide. <a href="/wiki/Cyanogen" title="Cyanogen">Cyanogen</a>, <a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">cyanogen chloride</a>, and the trimer <a href="/wiki/Cyanuric_chloride" title="Cyanuric chloride">cyanuric chloride</a> are derived from alkali metal cyanides.
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<div class="mw-heading mw-heading3"><h3 id="Medical_uses">Medical uses</h3><span class="mw-editsection">
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<p>The cyanide compound <a href="/wiki/Sodium_nitroprusside" title="Sodium nitroprusside">sodium nitroprusside</a> is used mainly in <a href="/wiki/Clinical_chemistry" title="Clinical chemistry">clinical chemistry</a> to measure <a href="/wiki/Urine" title="Urine">urine</a> <a href="/wiki/Ketone_bodies" title="Ketone bodies">ketone bodies</a> mainly as a follow-up to <a href="/wiki/Diabetic" class="mw-redirect" title="Diabetic">diabetic</a> patients. On occasion, it is used in emergency medical situations to produce a rapid decrease in <a href="/wiki/Blood_pressure" title="Blood pressure">blood pressure</a> in humans; it is also used as a <a href="/wiki/Vasodilator" class="mw-redirect" title="Vasodilator">vasodilator</a> in vascular research. The cobalt in artificial <a href="/wiki/Vitamin_B12" title="Vitamin B12">vitamin B<sub>12</sub></a> contains a cyanide ligand as an artifact of the purification process; this must be removed by the body before the vitamin molecule can be activated for biochemical use. During <a href="/wiki/World_War_I" title="World War I">World War I</a>, a copper cyanide compound was briefly used by <a href="/wiki/Japan" title="Japan">Japanese</a> physicians for the treatment of <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> and <a href="/wiki/Leprosy" title="Leprosy">leprosy</a>.<sup id="cite_ref-28" class="reference"><a href="#cite_note-28">[28]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Illegal_fishing_and_poaching">Illegal fishing and poaching</h3><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_fishing" title="Cyanide fishing">Cyanide fishing</a></div>
<p>Cyanides are illegally used to capture live fish near <a href="/wiki/Coral_reef" title="Coral reef">coral reefs</a> for the <a href="/wiki/Aquarium" title="Aquarium">aquarium</a> and seafood markets. The practice is controversial, dangerous, and damaging but is driven by the lucrative exotic fish market.<sup id="cite_ref-crc_29-0" class="reference"><a href="#cite_note-crc-29">[29]</a></sup>
</p><p>Poachers in Africa have been known to use cyanide to poison waterholes, to kill elephants for their ivory.<sup id="cite_ref-30" class="reference"><a href="#cite_note-30">[30]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Pest_control">Pest control</h3><span class="mw-editsection">
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<p><a href="/wiki/M44_(cyanide_device)" title="M44 (cyanide device)">M44 cyanide devices</a> are used in the United States to kill <a href="/wiki/Coyote" title="Coyote">coyotes</a> and other canids.<sup id="cite_ref-31" class="reference"><a href="#cite_note-31">[31]</a></sup> Cyanide is also used for pest control in <a href="/wiki/New_Zealand" title="New Zealand">New Zealand</a>, particularly for <a href="/wiki/Common_Brushtail_Possum_in_New_Zealand" class="mw-redirect" title="Common Brushtail Possum in New Zealand">possums</a>, an <a href="/wiki/Invasive_species_in_New_Zealand" title="Invasive species in New Zealand">introduced marsupial that threatens the conservation of native species</a> and spreads <a href="/wiki/Tuberculosis" title="Tuberculosis">tuberculosis</a> amongst cattle. Possums can become bait shy but the use of pellets containing the cyanide reduces bait shyness. Cyanide has been known to kill native birds, including the endangered <a href="/wiki/Kiwi_(bird)" title="Kiwi (bird)">kiwi</a>.<sup id="cite_ref-32" class="reference"><a href="#cite_note-32">[32]</a></sup> Cyanide is also effective for controlling the <a href="/wiki/Dama_wallaby" class="mw-redirect" title="Dama wallaby">dama wallaby</a>, another introduced marsupial pest in New Zealand.<sup id="cite_ref-33" class="reference"><a href="#cite_note-33">[33]</a></sup> A licence is required to store, handle and use cyanide in New Zealand.
</p><p>Cyanides are used as <a href="/wiki/Insecticide" title="Insecticide">insecticides</a> for fumigating ships.<sup id="cite_ref-34" class="reference"><a href="#cite_note-34">[34]</a></sup> Cyanide salts are used for killing ants,<sup id="cite_ref-EPAReg1994_35-0" class="reference"><a href="#cite_note-EPAReg1994-35">[35]</a></sup> and have in some places been used as rat poison<sup id="cite_ref-TariffInfo1921_36-0" class="reference"><a href="#cite_note-TariffInfo1921-36">[36]</a></sup> (the less toxic poison <a href="/wiki/Arsenic" title="Arsenic">arsenic</a> is more common).<sup id="cite_ref-PlanetDeadly2013_37-0" class="reference"><a href="#cite_note-PlanetDeadly2013-37">[37]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Niche_uses">Niche uses</h3><span class="mw-editsection">
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<p><a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">Potassium ferrocyanide</a> is used to achieve a blue color on cast <a href="/wiki/Bronze_sculpture" title="Bronze sculpture">bronze sculptures</a> during the final finishing stage of the sculpture. On its own, it will produce a very dark shade of blue and is often mixed with other chemicals to achieve the desired tint and hue. It is applied using a torch and paint brush while wearing the standard safety equipment used for any patina application: rubber gloves, safety glasses, and a respirator. The actual amount of cyanide in the mixture varies according to the recipes used by each foundry.
</p><p>Cyanide is also used in <a href="/wiki/Jewelry" class="mw-redirect" title="Jewelry">jewelry</a>-making and certain kinds of <a href="/wiki/Photography" title="Photography">photography</a> such as <a href="/wiki/Sepia_toning" class="mw-redirect" title="Sepia toning">sepia toning</a>.
</p><p>Although usually thought to be toxic, cyanide and cyanohydrins increase germination in various plant species.<sup id="cite_ref-38" class="reference"><a href="#cite_note-38">[38]</a></sup><sup id="cite_ref-39" class="reference"><a href="#cite_note-39">[39]</a></sup>
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<div class="mw-heading mw-heading4"><h4 id="Human_poisoning">Human poisoning</h4><span class="mw-editsection">
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<link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1033289096"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cyanide_poisoning" title="Cyanide poisoning">Cyanide poisoning</a></div>
<p>Deliberate cyanide poisoning of humans has occurred many times throughout history.<sup id="cite_ref-40" class="reference"><a href="#cite_note-40">[40]</a></sup>
Common salts such as <a href="/wiki/Sodium_cyanide" title="Sodium cyanide">sodium cyanide</a> are involatile but water-soluble, so are poisonous by ingestion. <a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">Hydrogen cyanide</a> is a gas, making it more indiscriminately dangerous, however it is lighter than air and rapidly disperses up into the atmosphere, which makes it ineffective as a <a href="/wiki/Chemical_weapon" title="Chemical weapon">chemical weapon</a>. Poisoning by hydrogen cyanide is more effective in an enclosed space, such as a <a href="/wiki/Gas_chamber" title="Gas chamber">gas chamber</a>. Most significantly, hydrogen cyanide released from pellets of <a href="/wiki/Zyklon-B" class="mw-redirect" title="Zyklon-B">Zyklon-B</a> was used extensively in the <a href="/wiki/Extermination_camp" title="Extermination camp">extermination camps</a> of <a href="/wiki/The_Holocaust" title="The Holocaust">the Holocaust</a>.
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<div class="mw-heading mw-heading4"><h4 id="Food_additive">Food additive</h4><span class="mw-editsection">
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<p>Because of the high stability of their complexation with <a href="/wiki/Iron" title="Iron">iron</a>, ferrocyanides (<a href="/wiki/Sodium_ferrocyanide" title="Sodium ferrocyanide">Sodium ferrocyanide</a> E535, <a href="/wiki/Potassium_ferrocyanide" title="Potassium ferrocyanide">Potassium ferrocyanide</a> E536, and Calcium ferrocyanide E538<sup id="cite_ref-41" class="reference"><a href="#cite_note-41">[41]</a></sup>) do not decompose to lethal levels in the human body and are used in the food industry as, e.g., an <a href="/wiki/Anticaking_agent" title="Anticaking agent">anticaking agent</a> in <a href="/wiki/Table_salt" class="mw-redirect" title="Table salt">table salt</a>.<sup id="cite_ref-42" class="reference"><a href="#cite_note-42">[42]</a></sup>
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<div class="mw-heading mw-heading2"><h2 id="Chemical_tests_for_cyanide">Chemical tests for cyanide</h2><span class="mw-editsection">
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<p>Cyanide is quantified by <a href="/wiki/Potentiometric_titration" title="Potentiometric titration">potentiometric titration</a>, a method widely used in gold mining. It can also be determined by titration with silver ion.
Some analyses begin with an air-purge of an acidified boiling solution, sweeping the vapors into a basic absorber solution. The cyanide salt absorbed in the basic solution is then analyzed.<sup id="cite_ref-43" class="reference"><a href="#cite_note-43">[43]</a></sup>
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<div class="mw-heading mw-heading3"><h3 id="Qualitative_tests">Qualitative tests</h3><span class="mw-editsection">
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<p>Because of the notorious toxicity of cyanide, many methods have been investigated. Benzidine gives a blue coloration in the presence of <a href="/wiki/Ferricyanide" title="Ferricyanide">ferricyanide</a>.<sup id="cite_ref-44" class="reference"><a href="#cite_note-44">[44]</a></sup> <a href="/wiki/Iron(II)_sulfate" title="Iron(II) sulfate">Iron(II) sulfate</a> added to a solution of cyanide, such as the filtrate from the <a href="/wiki/Sodium_fusion_test" title="Sodium fusion test">sodium fusion test</a>, gives <a href="/wiki/Prussian_blue" title="Prussian blue">prussian blue</a>. A solution of <a href="/wiki/1,4-Benzoquinone" title="1,4-Benzoquinone"><i>para</i>-benzoquinone</a> in <a href="/wiki/Dimethyl_sulfoxide" title="Dimethyl sulfoxide">DMSO</a> reacts with inorganic cyanide to form a cyano<a href="/wiki/Phenol" title="Phenol">phenol</a>, which is <a href="/wiki/Fluorescent" class="mw-redirect" title="Fluorescent">fluorescent</a>. Illumination with a <a href="/wiki/UV_light" class="mw-redirect" title="UV light">UV light</a> gives a green/blue glow if the test is positive.<sup id="cite_ref-45" class="reference"><a href="#cite_note-45">[45]</a></sup>
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<div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection">
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<style data-mw-deduplicate="TemplateStyles:r1217336898">.mw-parser-output .reflist{font-size:90%;margin-bottom:0.5em;list-style-type:decimal}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist">
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<li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text">Greenwood, N. N.; & Earnshaw, A. (1997). Chemistry of the Elements (2nd Edn.), Oxford:Butterworth-Heinemann. <style data-mw-deduplicate="TemplateStyles:r1215172403">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a{background-size:contain}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a{background-size:contain}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a{background-size:contain}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:#d33}.mw-parser-output .cs1-visible-error{color:#d33}.mw-parser-output .cs1-maint{display:none;color:#2C882D;margin-left:0.3em}.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911F}html.skin-theme-clientpref-night .mw-parser-output .cs1-visible-error,html.skin-theme-clientpref-night .mw-parser-output .cs1-hidden-error{color:#f8a397}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-visible-error,html.skin-theme-clientpref-os .mw-parser-output .cs1-hidden-error{color:#f8a397}html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911F}}</style><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-7506-3365-4" title="Special:BookSources/0-7506-3365-4">0-7506-3365-4</a>.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (July 2015)">page needed</span></a></i>]</sup></span>
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<li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text">G. L. Miessler and D. A. Tarr "Inorganic Chemistry" 3rd Ed, Pearson/Prentice Hall publisher, <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/0-13-035471-6" title="Special:BookSources/0-13-035471-6">0-13-035471-6</a>.<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (July 2015)">page needed</span></a></i>]</sup></span>
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<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=71&tid=19">"ToxFAQs for Cyanide"</a>. <a href="/wiki/Agency_for_Toxic_Substances_and_Disease_Registry" title="Agency for Toxic Substances and Disease Registry">Agency for Toxic Substances and Disease Registry</a>. July 2006<span class="reference-accessdate">. Retrieved <span class="nowrap">2008-06-28</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=ToxFAQs+for+Cyanide&rft.pub=Agency+for+Toxic+Substances+and+Disease+Registry&rft.date=2006-07&rft_id=https%3A%2F%2Fwwwn.cdc.gov%2FTSP%2FToxFAQs%2FToxFAQsLanding.aspx%3Fid%3D71%26tid%3D19&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFVetter2000" class="citation journal cs1">Vetter, J. (2000). "Plant cyanogenic glycosides". <i>Toxicon</i>. <b>38</b> (1): 11–36. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0041-0101%2899%2900128-2">10.1016/S0041-0101(99)00128-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10669009">10669009</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicon&rft.atitle=Plant+cyanogenic+glycosides&rft.volume=38&rft.issue=1&rft.pages=11-36&rft.date=2000&rft_id=info%3Adoi%2F10.1016%2FS0041-0101%2899%2900128-2&rft_id=info%3Apmid%2F10669009&rft.aulast=Vetter&rft.aufirst=J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-jones-5"><span class="mw-cite-backlink"><b><a href="#cite_ref-jones_5-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFJones1998" class="citation journal cs1">Jones, D. A. (1998). "Why are so many food plants cyanogenic?". <i><a href="/wiki/Phytochemistry_(journal)" title="Phytochemistry (journal)">Phytochemistry</a></i>. <b>47</b> (2): 155–162. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1998PChem..47..155J">1998PChem..47..155J</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0031-9422%2897%2900425-1">10.1016/S0031-9422(97)00425-1</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/9431670">9431670</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Phytochemistry&rft.atitle=Why+are+so+many+food+plants+cyanogenic%3F&rft.volume=47&rft.issue=2&rft.pages=155-162&rft.date=1998&rft_id=info%3Apmid%2F9431670&rft_id=info%3Adoi%2F10.1016%2FS0031-9422%2897%2900425-1&rft_id=info%3Abibcode%2F1998PChem..47..155J&rft.aulast=Jones&rft.aufirst=D.+A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFReissmannHochleitnerWangPaschos2003" class="citation journal cs1">Reissmann, Stefanie; Hochleitner, Elisabeth; Wang, Haofan; Paschos, Athanasios; Lottspeich, Friedrich; Glass, Richard S.; Böck, August (2003). <a rel="nofollow" class="external text" href="http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf">"Taming of a Poison: Biosynthesis of the NiFe-Hydrogenase Cyanide Ligands"</a> <span class="cs1-format">(PDF)</span>. <i>Science</i>. <b>299</b> (5609): 1067–1070. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2003Sci...299.1067R">2003Sci...299.1067R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1126%2Fscience.1080972">10.1126/science.1080972</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12586941">12586941</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:20488694">20488694</a>. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20201123134841/http://pdfs.semanticscholar.org/d359/5a5928df6c6209f88e105c937ccce0a05237.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2020-11-23.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Science&rft.atitle=Taming+of+a+Poison%3A+Biosynthesis+of+the+NiFe-Hydrogenase+Cyanide+Ligands&rft.volume=299&rft.issue=5609&rft.pages=1067-1070&rft.date=2003&rft_id=info%3Adoi%2F10.1126%2Fscience.1080972&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20488694%23id-name%3DS2CID&rft_id=info%3Apmid%2F12586941&rft_id=info%3Abibcode%2F2003Sci...299.1067R&rft.aulast=Reissmann&rft.aufirst=Stefanie&rft.au=Hochleitner%2C+Elisabeth&rft.au=Wang%2C+Haofan&rft.au=Paschos%2C+Athanasios&rft.au=Lottspeich%2C+Friedrich&rft.au=Glass%2C+Richard+S.&rft.au=B%C3%B6ck%2C+August&rft_id=http%3A%2F%2Fpdfs.semanticscholar.org%2Fd359%2F5a5928df6c6209f88e105c937ccce0a05237.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFPieniazekBradforth,_Stephen_E.Krylov,_Anna_I.2005" class="citation journal cs1">Pieniazek, Piotr A.; Bradforth, Stephen E.; Krylov, Anna I. (2005-12-07). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20080911131555/http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf">"Spectroscopy of the Cyano Radical in an Aqueous Environment"</a> <span class="cs1-format">(PDF)</span>. <i>The Journal of Physical Chemistry A</i>. <b>110</b> (14): 4854–4865. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2006JPCA..110.4854P">2006JPCA..110.4854P</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjp0545952">10.1021/jp0545952</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16599455">16599455</a>. Archived from <a rel="nofollow" class="external text" href="http://www-bcf.usc.edu/~krylov/pubs/pdf/jpca-110-4854.pdf">the original</a> <span class="cs1-format">(PDF)</span> on 2008-09-11<span class="reference-accessdate">. Retrieved <span class="nowrap">2008-08-23</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Physical+Chemistry+A&rft.atitle=Spectroscopy+of+the+Cyano+Radical+in+an+Aqueous+Environment&rft.volume=110&rft.issue=14&rft.pages=4854-4865&rft.date=2005-12-07&rft_id=info%3Apmid%2F16599455&rft_id=info%3Adoi%2F10.1021%2Fjp0545952&rft_id=info%3Abibcode%2F2006JPCA..110.4854P&rft.aulast=Pieniazek&rft.aufirst=Piotr+A.&rft.au=Bradforth%2C+Stephen+E.&rft.au=Krylov%2C+Anna+I.&rft_id=http%3A%2F%2Fwww-bcf.usc.edu%2F~krylov%2Fpubs%2Fpdf%2Fjpca-110-4854.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFRoth,_K._C.Meyer,_D._M.Hawkins,_I.1993" class="citation journal cs1">Roth, K. C.; Meyer, D. M.; <a href="/wiki/Isabel_Hawkins" title="Isabel Hawkins">Hawkins, I.</a> (1993). <a rel="nofollow" class="external text" href="http://articles.adsabs.harvard.edu/cgi-bin/nph-iarticle_query?1993ApJ...413L..67R&data_type=PDF_HIGH&whole_paper=YES&type=PRINTER&filetype=.pdf">"Interstellar Cyanogen and the Temperature of the Cosmic Microwave Background Radiation"</a> <span class="cs1-format">(PDF)</span>. <i>The Astrophysical Journal</i>. <b>413</b> (2): L67–L71. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1993ApJ...413L..67R">1993ApJ...413L..67R</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1086%2F186961">10.1086/186961</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Astrophysical+Journal&rft.atitle=Interstellar+Cyanogen+and+the+Temperature+of+the+Cosmic+Microwave+Background+Radiation&rft.volume=413&rft.issue=2&rft.pages=L67-L71&rft.date=1993&rft_id=info%3Adoi%2F10.1086%2F186961&rft_id=info%3Abibcode%2F1993ApJ...413L..67R&rft.au=Roth%2C+K.+C.&rft.au=Meyer%2C+D.+M.&rft.au=Hawkins%2C+I.&rft_id=http%3A%2F%2Farticles.adsabs.harvard.edu%2Fcgi-bin%2Fnph-iarticle_query%3F1993ApJ...413L..67R%26amp%3Bdata_type%3DPDF_HIGH%26amp%3Bwhole_paper%3DYES%26amp%3Btype%3DPRINTER%26amp%3Bfiletype%3D.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-CDC-9"><span class="mw-cite-backlink">^ <a href="#cite_ref-CDC_9-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-CDC_9-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFAnon2013" class="citation web cs1">Anon (June 27, 2013). <a rel="nofollow" class="external text" href="https://emergency.cdc.gov/agent/cyanide/basics/facts.asp">"Facts about cyanide:Where cyanide is found and how it is used"</a>. <i>CDC Emergency preparedness and response</i>. Centers for Disease Control and Prevention<span class="reference-accessdate">. Retrieved <span class="nowrap">10 December</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=CDC+Emergency+preparedness+and+response&rft.atitle=Facts+about+cyanide%3AWhere+cyanide+is+found+and+how+it+is+used&rft.date=2013-06-27&rft.au=Anon&rft_id=https%3A%2F%2Femergency.cdc.gov%2Fagent%2Fcyanide%2Fbasics%2Ffacts.asp&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-10"><span class="mw-cite-backlink"><b><a href="#cite_ref-10">^</a></b></span> <span class="reference-text"><a href="/wiki/IUPAC_Gold_Book" class="mw-redirect" title="IUPAC Gold Book">IUPAC Gold Book</a> <a rel="nofollow" class="external text" href="http://goldbook.iupac.org/N04151.html"><i>nitriles</i></a></span>
</li>
<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text">NCBI-MeSH <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/mesh/68009570"><i>Nitriles</i></a></span>
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<li id="cite_note-Ullmann-12"><span class="mw-cite-backlink">^ <a href="#cite_ref-Ullmann_12-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Ullmann_12-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-Ullmann_12-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFRuboKellensReddySteier2006" class="citation encyclopaedia cs1">Rubo, Andreas; Kellens, Raf; Reddy, Jay; Steier, Norbert; Hasenpusch, Wolfgang (2006). "Alkali Metal Cyanides". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.i01_i01">10.1002/14356007.i01_i01</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Alkali+Metal+Cyanides&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2006&rft_id=info%3Adoi%2F10.1002%2F14356007.i01_i01&rft.isbn=978-3527306732&rft.aulast=Rubo&rft.aufirst=Andreas&rft.au=Kellens%2C+Raf&rft.au=Reddy%2C+Jay&rft.au=Steier%2C+Norbert&rft.au=Hasenpusch%2C+Wolfgang&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFPollakRomederHagedornGelbke2000" class="citation encyclopaedia cs1">Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a17_363">10.1002/14356007.a17_363</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/3-527-30673-0" title="Special:BookSources/3-527-30673-0"><bdi>3-527-30673-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Nitriles&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2000&rft_id=info%3Adoi%2F10.1002%2F14356007.a17_363&rft.isbn=3-527-30673-0&rft.aulast=Pollak&rft.aufirst=Peter&rft.au=Romeder%2C+G%C3%A9rard&rft.au=Hagedorn%2C+Ferdinand&rft.au=Gelbke%2C+Heinz-Peter&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-Young_1995-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-Young_1995_14-0">^</a></b></span> <span class="reference-text">Young, C. A., & Jordan, T. S. (1995, May). Cyanide remediation: current and past technologies. In: Proceedings of the 10th Annual Conference on Hazardous Waste Research (pp. 104–129). Kansas State University: Manhattan, KS. <a rel="nofollow" class="external free" href="https://engg.ksu.edu/HSRC/95Proceed/young.pdf">https://engg.ksu.edu/HSRC/95Proceed/young.pdf</a></span>
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<li id="cite_note-SRK-15"><span class="mw-cite-backlink"><b><a href="#cite_ref-SRK_15-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFDmitry_Yermakov" class="citation web cs1">Dmitry Yermakov. <a rel="nofollow" class="external text" href="https://www.srk.com/en/publications/cyanide-destruction">"Cyanide Destruction | SRK Consulting"</a>. <i>srk.com</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2 March</span> 2021</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=srk.com&rft.atitle=Cyanide+Destruction+%7C+SRK+Consulting&rft.au=Dmitry+Yermakov&rft_id=https%3A%2F%2Fwww.srk.com%2Fen%2Fpublications%2Fcyanide-destruction&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-Botz-16"><span class="mw-cite-backlink"><b><a href="#cite_ref-Botz_16-0">^</a></b></span> <span class="reference-text">Botz Michael M. Overview of cyanide treatment methods. Elbow Creek Engineering, Inc. <a rel="nofollow" class="external free" href="http://www.botz.com/MEMCyanideTreatment.pdf">http://www.botz.com/MEMCyanideTreatment.pdf</a></span>
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<li id="cite_note-17"><span class="mw-cite-backlink"><b><a href="#cite_ref-17">^</a></b></span> <span class="reference-text">Sharpe, A. G. The Chemistry of Cyano Complexes of the Transition Metals; Academic Press: London, 1976<sup class="noprint Inline-Template" style="white-space:nowrap;">[<i><a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources"><span title="This citation requires a reference to the specific page or range of pages in which the material appears. (July 2015)">page needed</span></a></i>]</sup></span>
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<li id="cite_note-Holl-18"><span class="mw-cite-backlink"><b><a href="#cite_ref-Holl_18-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFHolleman,_A._F.Wiberg,_E.2001" class="citation book cs1">Holleman, A. F.; Wiberg, E. (2001). <i>Inorganic Chemistry</i>. San Diego: Academic Press. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-12-352651-9" title="Special:BookSources/978-0-12-352651-9"><bdi>978-0-12-352651-9</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Inorganic+Chemistry&rft.place=San+Diego&rft.pub=Academic+Press&rft.date=2001&rft.isbn=978-0-12-352651-9&rft.au=Holleman%2C+A.+F.&rft.au=Wiberg%2C+E.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-19"><span class="mw-cite-backlink"><b><a href="#cite_ref-19">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFAndrussow1927" class="citation journal cs1 cs1-prop-foreign-lang-source"><a href="/wiki/Leonid_Andrussow" title="Leonid Andrussow">Andrussow, Leonid</a> (1927). "Über die schnell verlaufenden katalytischen Prozesse in strömenden Gasen und die Ammoniak-Oxydation (V)" [About the quicka catalytic processes in flowing gases and the ammonia oxidation (V)]. <i>Berichte der Deutschen Chemischen Gesellschaft</i> (in German). <b>60</b> (8): 2005–2018. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fcber.19270600857">10.1002/cber.19270600857</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Berichte+der+Deutschen+Chemischen+Gesellschaft&rft.atitle=%C3%9Cber+die+schnell+verlaufenden+katalytischen+Prozesse+in+str%C3%B6menden+Gasen+und+die+Ammoniak-Oxydation+%28V%29&rft.volume=60&rft.issue=8&rft.pages=2005-2018&rft.date=1927&rft_id=info%3Adoi%2F10.1002%2Fcber.19270600857&rft.aulast=Andrussow&rft.aufirst=Leonid&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-20"><span class="mw-cite-backlink"><b><a href="#cite_ref-20">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFAndrussow1935" class="citation journal cs1 cs1-prop-foreign-lang-source">Andrussow, L. (1935). "Über die katalytische Oxydation von Ammoniak-Methan-Gemischen zu Blausäure" [About the catalytic oxidation of ammonia-methane mixtures to cyanide]. <i><a href="/wiki/Angewandte_Chemie" title="Angewandte Chemie">Angewandte Chemie</a></i> (in German). <b>48</b> (37): 593–595. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/1935AngCh..48..593A">1935AngCh..48..593A</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fange.19350483702">10.1002/ange.19350483702</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Angewandte+Chemie&rft.atitle=%C3%9Cber+die+katalytische+Oxydation+von+Ammoniak-Methan-Gemischen+zu+Blaus%C3%A4ure&rft.volume=48&rft.issue=37&rft.pages=593-595&rft.date=1935&rft_id=info%3Adoi%2F10.1002%2Fange.19350483702&rft_id=info%3Abibcode%2F1935AngCh..48..593A&rft.aulast=Andrussow&rft.aufirst=L.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-21"><span class="mw-cite-backlink"><b><a href="#cite_ref-21">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFNelsonCox2000" class="citation book cs1">Nelson, David L.; Cox, Michael M. (2000). <a rel="nofollow" class="external text" href="https://archive.org/details/lehningerprincip01lehn/page/668"><i>Lehniger Principles of Biochemistry</i></a> (3rd ed.). New York: <a href="/wiki/Worth_Publishers" class="mw-redirect" title="Worth Publishers">Worth Publishers</a>. pp. <a rel="nofollow" class="external text" href="https://archive.org/details/lehningerprincip01lehn/page/668">668, 670–71, 676</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-57259-153-0" title="Special:BookSources/978-1-57259-153-0"><bdi>978-1-57259-153-0</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Lehniger+Principles+of+Biochemistry&rft.place=New+York&rft.pages=668%2C+670-71%2C+676&rft.edition=3rd&rft.pub=Worth+Publishers&rft.date=2000&rft.isbn=978-1-57259-153-0&rft.aulast=Nelson&rft.aufirst=David+L.&rft.au=Cox%2C+Michael+M.&rft_id=https%3A%2F%2Farchive.org%2Fdetails%2Flehningerprincip01lehn%2Fpage%2F668&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-Biller-22"><span class="mw-cite-backlink">^ <a href="#cite_ref-Biller_22-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Biller_22-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFBiller2007" class="citation book cs1">Biller, José (2007). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=SRIvmTVcYBwC&pg=PA939">"163"</a>. <i>Interface of neurology and internal medicine</i> (illustrated ed.). Lippincott Williams & Wilkins. p. 939. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-7817-7906-7" title="Special:BookSources/978-0-7817-7906-7"><bdi>978-0-7817-7906-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=163&rft.btitle=Interface+of+neurology+and+internal+medicine&rft.pages=939&rft.edition=illustrated&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2007&rft.isbn=978-0-7817-7906-7&rft.aulast=Biller&rft.aufirst=Jos%C3%A9&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DSRIvmTVcYBwC%26pg%3DPA939&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-23"><span class="mw-cite-backlink"><b><a href="#cite_ref-23">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf">"MSDS of trimethylsilyl cyanide"</a> <span class="cs1-format">(PDF)</span>. Gelest Inc. 2008. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221010/https://www.gelest.com/wp-content/uploads/product_msds/SIT8585.1-msds.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2022-10-10<span class="reference-accessdate">. Retrieved <span class="nowrap">2022-08-16</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=MSDS+of+trimethylsilyl+cyanide&rft.pub=Gelest+Inc&rft.date=2008&rft_id=https%3A%2F%2Fwww.gelest.com%2Fwp-content%2Fuploads%2Fproduct_msds%2FSIT8585.1-msds.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><i><a rel="nofollow" class="external text" href="https://emedicine.medscape.com/article/814287-treatment">Cyanide Toxicity~treatment</a></i> at <a href="/wiki/EMedicine" title="EMedicine">eMedicine</a></span>
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<li id="cite_note-25"><span class="mw-cite-backlink"><b><a href="#cite_ref-25">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFChaudharyGupta2012" class="citation journal cs1">Chaudhary, M.; Gupta, R. (2012). "Cyanide Detoxifying Enzyme: Rhodanese". <i>Current Biotechnology</i>. <b>1</b> (4): 327–335. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2174%2F2211550111201040327">10.2174/2211550111201040327</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Current+Biotechnology&rft.atitle=Cyanide+Detoxifying+Enzyme%3A+Rhodanese&rft.volume=1&rft.issue=4&rft.pages=327-335&rft.date=2012&rft_id=info%3Adoi%2F10.2174%2F2211550111201040327&rft.aulast=Chaudhary&rft.aufirst=M.&rft.au=Gupta%2C+R.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation report cs1"><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxprofiles/tp8.pdf">Toxicological Profile for Cyanide</a> <span class="cs1-format">(PDF)</span> (Report). U.S. Department of Health and Human Services. 2006. pp. 18–19. <a rel="nofollow" class="external text" href="https://web.archive.org/web/20040331014808/http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2004-03-31.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=report&rft.btitle=Toxicological+Profile+for+Cyanide&rft.pages=18-19&rft.pub=U.S.+Department+of+Health+and+Human+Services&rft.date=2006&rft_id=https%3A%2F%2Fwww.atsdr.cdc.gov%2Ftoxprofiles%2Ftp8.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-27"><span class="mw-cite-backlink"><b><a href="#cite_ref-27">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFKumarSahaSaritaMayur_B.2016" class="citation journal cs1">Kumar, Rahul; Saha, Shouvik; Sarita, Dhaka; Mayur B., Kurade; Kang, Chan Ung; Baek, Seung Han; Jeong, Byong-Hun (2016). <a rel="nofollow" class="external text" href="https://www.tandfonline.com/doi/full/10.1080/12269328.2016.1218303">"Remediation of cyanide-contaminated environments through microbes and plants: a review of current knowledge and future perspectives"</a>. <i>Geosystem Engineering</i>. <b>70</b> (1): 28–40. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1080%2F12269328.2016.1218303">10.1080/12269328.2016.1218303</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:132571397">132571397</a><span class="reference-accessdate">. Retrieved <span class="nowrap">24 April</span> 2022</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Geosystem+Engineering&rft.atitle=Remediation+of+cyanide-contaminated+environments+through+microbes+and+plants%3A+a+review+of+current+knowledge+and+future+perspectives&rft.volume=70&rft.issue=1&rft.pages=28-40&rft.date=2016&rft_id=info%3Adoi%2F10.1080%2F12269328.2016.1218303&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A132571397%23id-name%3DS2CID&rft.aulast=Kumar&rft.aufirst=Rahul&rft.au=Saha%2C+Shouvik&rft.au=Sarita%2C+Dhaka&rft.au=Mayur+B.%2C+Kurade&rft.au=Kang%2C+Chan+Ung&rft.au=Baek%2C+Seung+Han&rft.au=Jeong%2C+Byong-Hun&rft_id=https%3A%2F%2Fwww.tandfonline.com%2Fdoi%2Ffull%2F10.1080%2F12269328.2016.1218303&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-28"><span class="mw-cite-backlink"><b><a href="#cite_ref-28">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFTakano1916" class="citation journal cs1">Takano, R. (August 1916). <a rel="nofollow" class="external text" href="http://www.jem.org/cgi/content/abstract/24/2/207">"The treatment of leprosy with cyanocuprol"</a>. <i>The Journal of Experimental Medicine</i>. <b>24</b> (2): 207–211. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1084%2Fjem.24.2.207">10.1084/jem.24.2.207</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2125457">2125457</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/19868035">19868035</a><span class="reference-accessdate">. Retrieved <span class="nowrap">2008-06-28</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Journal+of+Experimental+Medicine&rft.atitle=The+treatment+of+leprosy+with+cyanocuprol&rft.volume=24&rft.issue=2&rft.pages=207-211&rft.date=1916-08&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC2125457%23id-name%3DPMC&rft_id=info%3Apmid%2F19868035&rft_id=info%3Adoi%2F10.1084%2Fjem.24.2.207&rft.aulast=Takano&rft.aufirst=R.&rft_id=http%3A%2F%2Fwww.jem.org%2Fcgi%2Fcontent%2Fabstract%2F24%2F2%2F207&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-crc-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-crc_29-0">^</a></b></span> <span class="reference-text">Dzombak, David A; Ghosh, Rajat S; Wong-Chong, George M. <i>Cyanide in Water and Soil</i>. <a href="/wiki/CRC_Press" title="CRC Press">CRC Press</a>, 2006, Chapter 11.2: "Use of Cyanide for Capturing Live Reef Fish".</span>
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<li id="cite_note-30"><span class="mw-cite-backlink"><b><a href="#cite_ref-30">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.abc.net.au/news/2013-09-25/zimbabwe-poachers-kill-80-elephants-with-cyanide/4981372">Poachers kill 80 elephants with cyanide in Zimbabwe</a> <i>ABC News</i>, 25 September 2013. Retrieved 30 October 2015.</span>
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<li id="cite_note-31"><span class="mw-cite-backlink"><b><a href="#cite_ref-31">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFShivikMastroYoung2014" class="citation journal cs1">Shivik, John A.; Mastro, Lauren; Young, Julie K. (2014). <a rel="nofollow" class="external text" href="http://digitalcommons.unl.edu/cgi/viewcontent.cgi?article=2419&context=icwdm_usdanwrc">"Animal attendance at M-44 sodium cyanide ejector sites for coyotes"</a>. <i>Wildlife Society Bulletin</i>. <b>38</b> (1): 217–220. <a href="/wiki/Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2014WSBu...38..217S">2014WSBu...38..217S</a>. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2Fwsb.361">10.1002/wsb.361</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Wildlife+Society+Bulletin&rft.atitle=Animal+attendance+at+M-44+sodium+cyanide+ejector+sites+for+coyotes&rft.volume=38&rft.issue=1&rft.pages=217-220&rft.date=2014&rft_id=info%3Adoi%2F10.1002%2Fwsb.361&rft_id=info%3Abibcode%2F2014WSBu...38..217S&rft.aulast=Shivik&rft.aufirst=John+A.&rft.au=Mastro%2C+Lauren&rft.au=Young%2C+Julie+K.&rft_id=http%3A%2F%2Fdigitalcommons.unl.edu%2Fcgi%2Fviewcontent.cgi%3Farticle%3D2419%26context%3Dicwdm_usdanwrc&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-32"><span class="mw-cite-backlink"><b><a href="#cite_ref-32">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFGreen2004" class="citation web cs1">Green, Wren (July 2004). <a rel="nofollow" class="external text" href="http://www.doc.govt.nz/upload/documents/conservation/threats-and-impacts/animal-pests/use-of-1080-04.pdf">"The use of 1080 for pest control"</a> <span class="cs1-format">(PDF)</span>. New Zealand Department of Conservation<span class="reference-accessdate">. Retrieved <span class="nowrap">8 June</span> 2011</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=unknown&rft.btitle=The+use+of+1080+for+pest+control&rft.pub=New+Zealand+Department+of+Conservation&rft.date=2004-07&rft.aulast=Green&rft.aufirst=Wren&rft_id=http%3A%2F%2Fwww.doc.govt.nz%2Fupload%2Fdocuments%2Fconservation%2Fthreats-and-impacts%2Fanimal-pests%2Fuse-of-1080-04.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-33"><span class="mw-cite-backlink"><b><a href="#cite_ref-33">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFShapiro2011" class="citation journal cs1">Shapiro, Lee; et al. (21 March 2011). <a rel="nofollow" class="external text" href="http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf">"Effectiveness of cyanide pellets for control of dama wallabies (Macropus eugenii)"</a> <span class="cs1-format">(PDF)</span>. <i>New Zealand Journal of Ecology</i>. <b>35</b> (3). <a rel="nofollow" class="external text" href="https://web.archive.org/web/20150203010818/http://newzealandecology.org/nzje/new_issues/NZJEcol35_3_287.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2015-02-03.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=New+Zealand+Journal+of+Ecology&rft.atitle=Effectiveness+of+cyanide+pellets+for+control+of+dama+wallabies+%28Macropus+eugenii%29&rft.volume=35&rft.issue=3&rft.date=2011-03-21&rft.aulast=Shapiro&rft.aufirst=Lee&rft_id=http%3A%2F%2Fnewzealandecology.org%2Fnzje%2Fnew_issues%2FNZJEcol35_3_287.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-34"><span class="mw-cite-backlink"><b><a href="#cite_ref-34">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/sodium_cyanide">"Sodium Cyanide"</a>. <i>PubChem</i>. National Center for Biotechnology Information. 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">2 September</span> 2016</span>. <q>Cyanide and hydrogen cyanide are used in electroplating, metallurgy, organic chemicals production, photographic developing, manufacture of plastics, fumigation of ships, and some mining processes.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PubChem&rft.atitle=Sodium+Cyanide&rft.date=2016&rft_id=https%3A%2F%2Fpubchem.ncbi.nlm.nih.gov%2Fcompound%2Fsodium_cyanide&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-EPAReg1994-35"><span class="mw-cite-backlink"><b><a href="#cite_ref-EPAReg1994_35-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf">"Reregistration Eligibility Decision (RED) Sodium Cyanide"</a> <span class="cs1-format">(PDF)</span>. <i>EPA.gov</i>. 1 September 1994. p. 7. <a rel="nofollow" class="external text" href="https://ghostarchive.org/archive/20221010/https://archive.epa.gov/pesticides/reregistration/web/pdf/3086.pdf">Archived</a> <span class="cs1-format">(PDF)</span> from the original on 2022-10-10<span class="reference-accessdate">. Retrieved <span class="nowrap">2 September</span> 2016</span>. <q>Sodium cyanide was initially registered as a pesticide on December 23, 1947, to control ants on uncultivated agricultural and non-agricultural areas.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=EPA.gov&rft.atitle=Reregistration+Eligibility+Decision+%28RED%29+Sodium+Cyanide&rft.pages=7&rft.date=1994-09-01&rft_id=https%3A%2F%2Farchive.epa.gov%2Fpesticides%2Freregistration%2Fweb%2Fpdf%2F3086.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-TariffInfo1921-36"><span class="mw-cite-backlink"><b><a href="#cite_ref-TariffInfo1921_36-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.abebooks.com/servlet/SearchResults?tn=Tariff+Information,+1921">"Tariff Information, 1921: Hearings on General Tariff Revision Before the Committee on Ways and Means, House of Representatives"</a>. <i>AbeBooks.com</i>. US Congress, House Committee on Ways and Means, US Government Printing Office. 1921. p. 3987<span class="reference-accessdate">. Retrieved <span class="nowrap">2 September</span> 2016</span>. <q>Another field in which cyanide is used in growing quantity is the eradication of rats and other vermin – especially in the fight against typhus.</q></cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=AbeBooks.com&rft.atitle=Tariff+Information%2C+1921%3A+Hearings+on+General+Tariff+Revision+Before+the+Committee+on+Ways+and+Means%2C+House+of+Representatives&rft.pages=3987&rft.date=1921&rft_id=http%3A%2F%2Fwww.abebooks.com%2Fservlet%2FSearchResults%3Ftn%3DTariff%2BInformation%2C%2B1921&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-PlanetDeadly2013-37"><span class="mw-cite-backlink"><b><a href="#cite_ref-PlanetDeadly2013_37-0">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://web.archive.org/web/20160511033535/http://www.planetdeadly.com/human/deadliest-poisons-man">"Deadliest Poisons Used by Man"</a>. <i>PlanetDeadly.com</i>. 18 November 2013. Archived from <a rel="nofollow" class="external text" href="http://www.planetdeadly.com/human/deadliest-poisons-man">the original</a> on 11 May 2016<span class="reference-accessdate">. Retrieved <span class="nowrap">2 September</span> 2016</span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=PlanetDeadly.com&rft.atitle=Deadliest+Poisons+Used+by+Man&rft.date=2013-11-18&rft_id=http%3A%2F%2Fwww.planetdeadly.com%2Fhuman%2Fdeadliest-poisons-man&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
</li>
<li id="cite_note-38"><span class="mw-cite-backlink"><b><a href="#cite_ref-38">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFTaylorsonHendricks1973" class="citation journal cs1">Taylorson, R.; Hendricks, SB (1973). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC366431">"Promotion of Seed Germination by Cyanide"</a>. <i>Plant Physiol</i>. <b>52</b> (1): 23–27. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1104%2Fpp.52.1.23">10.1104/pp.52.1.23</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC366431">366431</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/16658492">16658492</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plant+Physiol.&rft.atitle=Promotion+of+Seed+Germination+by+Cyanide&rft.volume=52&rft.issue=1&rft.pages=23-27&rft.date=1973&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC366431%23id-name%3DPMC&rft_id=info%3Apmid%2F16658492&rft_id=info%3Adoi%2F10.1104%2Fpp.52.1.23&rft.aulast=Taylorson&rft.aufirst=R.&rft.au=Hendricks%2C+SB&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC366431&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
</li>
<li id="cite_note-39"><span class="mw-cite-backlink"><b><a href="#cite_ref-39">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFMullickChatterji1967" class="citation journal cs1">Mullick, P.; Chatterji, U. N. (1967). "Effect of sodium cyanide on germination of two leguminous seeds". <i>Plant Systematics and Evolution</i>. <b>114</b>: 88–91. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF01373937">10.1007/BF01373937</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:2533762">2533762</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Plant+Systematics+and+Evolution&rft.atitle=Effect+of+sodium+cyanide+on+germination+of+two+leguminous+seeds&rft.volume=114&rft.pages=88-91&rft.date=1967&rft_id=info%3Adoi%2F10.1007%2FBF01373937&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A2533762%23id-name%3DS2CID&rft.aulast=Mullick&rft.aufirst=P.&rft.au=Chatterji%2C+U.+N.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
</li>
<li id="cite_note-40"><span class="mw-cite-backlink"><b><a href="#cite_ref-40">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFBernan2008" class="citation book cs1">Bernan (2008). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oiw2ZzsBvsoC"><i>Medical Management of Chemical Casualties Handbook</i></a> (4th ed.). Government Printing Off. p. 41. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-16-081320-7" title="Special:BookSources/978-0-16-081320-7"><bdi>978-0-16-081320-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Medical+Management+of+Chemical+Casualties+Handbook&rft.pages=41&rft.edition=4th&rft.pub=Government+Printing+Off&rft.date=2008&rft.isbn=978-0-16-081320-7&rft.au=Bernan&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3Doiw2ZzsBvsoC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span>, <a rel="nofollow" class="external text" href="https://books.google.com/books?id=oiw2ZzsBvsoC&pg=PA41">Extract p. 41</a></span>
</li>
<li id="cite_note-41"><span class="mw-cite-backlink"><b><a href="#cite_ref-41">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFBenderBender1997" class="citation book cs1">Bender, David A.; Bender, Arnold Eric (1997). <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IrYfDEl7XPYC"><i>Benders' dictionary of nutrition and food technology</i></a> (7th ed.). Woodhead Publishing. p. 459. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-1-85573-475-3" title="Special:BookSources/978-1-85573-475-3"><bdi>978-1-85573-475-3</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Benders%27+dictionary+of+nutrition+and+food+technology&rft.pages=459&rft.edition=7th&rft.pub=Woodhead+Publishing&rft.date=1997&rft.isbn=978-1-85573-475-3&rft.aulast=Bender&rft.aufirst=David+A.&rft.au=Bender%2C+Arnold+Eric&rft_id=https%3A%2F%2Fbooks.google.com%2Fbooks%3Fid%3DIrYfDEl7XPYC&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span> <a rel="nofollow" class="external text" href="https://books.google.com/books?id=IrYfDEl7XPYC&pg=PA459">Extract of page 459</a></span>
</li>
<li id="cite_note-42"><span class="mw-cite-backlink"><b><a href="#cite_ref-42">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFSchulzHadelerDeutsche_Forschungsgemeinschaft2003" class="citation book cs1">Schulz, Horst D.; Hadeler, Astrid; Deutsche Forschungsgemeinschaft (2003). <a rel="nofollow" class="external text" href="http://onlinelibrary.wiley.com/doi/10.1002/9783527609703"><i>Geochemical processes in soil and groundwater: measurement – modelling – upscaling</i></a>. Wiley-VCH. p. 67. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F9783527609703">10.1002/9783527609703</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3-527-27766-7" title="Special:BookSources/978-3-527-27766-7"><bdi>978-3-527-27766-7</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Geochemical+processes+in+soil+and+groundwater%3A+measurement+%E2%80%93+modelling+%E2%80%93+upscaling&rft.pages=67&rft.pub=Wiley-VCH&rft.date=2003&rft_id=info%3Adoi%2F10.1002%2F9783527609703&rft.isbn=978-3-527-27766-7&rft.aulast=Schulz&rft.aufirst=Horst+D.&rft.au=Hadeler%2C+Astrid&rft.au=Deutsche+Forschungsgemeinschaft&rft_id=http%3A%2F%2Fonlinelibrary.wiley.com%2Fdoi%2F10.1002%2F9783527609703&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
</li>
<li id="cite_note-43"><span class="mw-cite-backlink"><b><a href="#cite_ref-43">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFGailGosKulzerLorösch2004" class="citation encyclopaedia cs1">Gail, Ernst; Gos, Stephen; Kulzer, Rupprecht; Lorösch, Jürgen; Rubo, Andreas; Sauer, Manfred (2004). "Cyano Compounds, Inorganic". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a08_159.pub2">10.1002/14356007.a08_159.pub2</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Cyano+Compounds%2C+Inorganic&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2004&rft_id=info%3Adoi%2F10.1002%2F14356007.a08_159.pub2&rft.isbn=978-3527306732&rft.aulast=Gail&rft.aufirst=Ernst&rft.au=Gos%2C+Stephen&rft.au=Kulzer%2C+Rupprecht&rft.au=Lor%C3%B6sch%2C+J%C3%BCrgen&rft.au=Rubo%2C+Andreas&rft.au=Sauer%2C+Manfred&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-44"><span class="mw-cite-backlink"><b><a href="#cite_ref-44">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFSchwenecke,_H.Mayer,_D.2005" class="citation encyclopaedia cs1">Schwenecke, H.; Mayer, D. (2005). "Benzidine and Benzidine Derivatives". <i><a href="/wiki/Ullmann%27s_Encyclopedia_of_Industrial_Chemistry" title="Ullmann's Encyclopedia of Industrial Chemistry">Ullmann's Encyclopedia of Industrial Chemistry</a></i>. Weinheim: Wiley-VCH. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14356007.a03_539">10.1002/14356007.a03_539</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-3527306732" title="Special:BookSources/978-3527306732"><bdi>978-3527306732</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Benzidine+and+Benzidine+Derivatives&rft.btitle=Ullmann%27s+Encyclopedia+of+Industrial+Chemistry&rft.place=Weinheim&rft.pub=Wiley-VCH&rft.date=2005&rft_id=info%3Adoi%2F10.1002%2F14356007.a03_539&rft.isbn=978-3527306732&rft.au=Schwenecke%2C+H.&rft.au=Mayer%2C+D.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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<li id="cite_note-45"><span class="mw-cite-backlink"><b><a href="#cite_ref-45">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1215172403"><cite id="CITEREFGanjelooIsomMorganWay1980" class="citation journal cs1">Ganjeloo, A; Isom, GE; Morgan, RL; Way, JL (1980). "Fluorometric determination of cyanide in biological fluids with p-benzoquinone*1". <i><a href="/wiki/Toxicology_and_Applied_Pharmacology" title="Toxicology and Applied Pharmacology">Toxicology and Applied Pharmacology</a></i>. <b>55</b> (1): 103–107. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2F0041-008X%2880%2990225-2">10.1016/0041-008X(80)90225-2</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/7423496">7423496</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Toxicology+and+Applied+Pharmacology&rft.atitle=Fluorometric+determination+of+cyanide+in+biological+fluids+with+p-benzoquinone%2A1&rft.volume=55&rft.issue=1&rft.pages=103-107&rft.date=1980&rft_id=info%3Adoi%2F10.1016%2F0041-008X%2880%2990225-2&rft_id=info%3Apmid%2F7423496&rft.aulast=Ganjeloo&rft.aufirst=A&rft.au=Isom%2C+GE&rft.au=Morgan%2C+RL&rft.au=Way%2C+JL&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACyanide" class="Z3988"></span></span>
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</ol></div></div>
<div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection">
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<div class="side-box-text plainlist"><a href="/wiki/Wikisource" title="Wikisource">Wikisource</a> has the text of the <a href="/wiki/Encyclop%C3%A6dia_Britannica_Eleventh_Edition" title="Encyclopædia Britannica Eleventh Edition">1911 <i>Encyclopædia Britannica</i></a> article "<span style="font-weight:bold;"><a href="https://en.wikisource.org/wiki/1911_Encyclop%C3%A6dia_Britannica/Cyanide" class="extiw" title="wikisource:1911 Encyclopædia Britannica/Cyanide">Cyanide</a></span>".</div></div>
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<div class="side-box-text plainlist">Wikimedia Commons has media related to <span style="font-weight: bold; font-style: italic;"><a href="https://commons.wikimedia.org/wiki/Category:Cyanides" class="extiw" title="commons:Category:Cyanides">Cyanides</a></span>.</div></div>
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<ul><li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20100528070140/http://www.atsdr.cdc.gov/MMG/MMG.asp?id=1073&tid=19">ATSDR medical management guidelines for cyanide poisoning (US)</a></li>
<li><a rel="nofollow" class="external text" href="http://www.hse.gov.uk/pubns/firindex.htm">HSE recommendations for first aid treatment of cyanide poisoning (UK)</a></li>
<li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/cicads/cicads/cicad61.htm">Hydrogen cyanide and cyanides</a> (<a href="/wiki/CICAD" class="mw-redirect" title="CICAD">CICAD</a> 61)</li>
<li><a rel="nofollow" class="external text" href="http://www.inchem.org/documents/antidote/antidote/ant02.htm#SubSectionNumber:1.13.1">IPCS/CEC Evaluation of antidotes for poisoning by cyanides</a></li>
<li><a rel="nofollow" class="external text" href="https://web.archive.org/web/20060517035532/http://www.npi.gov.au/database/substance-info/profiles/29.html">National Pollutant Inventory – Cyanide compounds fact sheet</a></li>
<li><a rel="nofollow" class="external text" href="http://www.snopes.com/food/warnings/apples.asp#add">Eating apple seeds is safe despite the small amount of cyanide</a></li>
<li><a rel="nofollow" class="external text" href="https://www.atsdr.cdc.gov/toxprofiles/tp8.pdf">Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, July 2006</a></li></ul>
<dl><dt>Safety data (French)</dt></dl>
<ul><li>Institut national de recherche et de sécurité (1997). "<a rel="nofollow" class="external text" href="https://web.archive.org/web/20060220084315/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/860430FE710FCFD7C1256CE8004F67CB/$File/ft4.pdf">Cyanure d'hydrogène et solutions aqueuses</a>". <i>Fiche toxicologique n° 4</i>, Paris: INRS, 5 pp. (PDF file, <span class="languageicon">(in French)</span>)</li>
<li>Institut national de recherche et de sécurité (1997). "<a rel="nofollow" class="external text" href="https://web.archive.org/web/20060220084330/http://www.inrs.fr/inrs-pub/inrs01.nsf/inrs01_ftox_view/48145297F4EF18BBC1256CE8005A9FC2/$File/ft111.pdf">Cyanure de sodium. Cyanure de potassium</a>". <i>Fiche toxicologique n° 111</i>, Paris: INRS, 6 pp. (PDF file, <span class="languageicon">(in French)</span>)</li></ul>
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.navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}</style></div><div role="navigation" class="navbox" aria-labelledby="Salts_and_covalent_derivatives_of_the_cyanide_ion" style="display:table;;padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit;table-layout:fixed;"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1063604349">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Cyanides" title="Template:Cyanides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Cyanides" title="Template talk:Cyanides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Cyanides" title="Special:EditPage/Template:Cyanides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Salts_and_covalent_derivatives_of_the_cyanide_ion" style="font-size:114%;margin:0 4em">Salts and covalent derivatives of the <a class="mw-selflink selflink">cyanide</a> ion</div></th></tr><tr><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0;border-width:0;"><div style="padding:0"><div class="mw-collapsible-content" style="overflow-x:auto">
<table class="center">
<tbody><tr style="background-color:mistyrose">
<td><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a>
</td>
<td style="background-color:white;border:none">
</td>
<td style="background-color:white;border:none" colspan="11" rowspan="3">
</td>
<td style="background-color:white;border:none" colspan="5">
</td>
<td>He
</td></tr>
<tr style="background-color:mistyrose">
<td><a href="/wiki/Lithium_cyanide" title="Lithium cyanide">LiCN</a>
</td>
<td><a href="/w/index.php?title=Beryllium_cyanide&action=edit&redlink=1" class="new" title="Beryllium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Be(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/w/index.php?title=Boron_cyanide&action=edit&redlink=1" class="new" title="Boron cyanide (page does not exist)">B(CN)<sub>3</sub></a>
</td>
<td><a href="/wiki/Tetracyanomethane" title="Tetracyanomethane">C(CN)<sub>4</sub></a><br /><a href="/wiki/Dicyanoacetylene" title="Dicyanoacetylene">C<sub>2</sub>(CN)<sub>2</sub></a>
</td>
<td><a href="/wiki/Ammonium_cyanide" title="Ammonium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">NH<sub class="template-chem2-sub">4</sub>CN</span></a><br /><a href="/wiki/Nitrosyl_cyanide" title="Nitrosyl cyanide">ONCN</a><br /><a href="/wiki/Nitryl_cyanide" title="Nitryl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O<sub class="template-chem2-sub">2</sub>NCN</span></a><br /><a href="/wiki/Cyanogen_azide" title="Cyanogen azide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">N<sub class="template-chem2-sub">3</sub>CN</span></a>
</td>
<td><a href="/wiki/Cyanate" title="Cyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">OCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isocyanate" title="Isocyanate">-NCO</a><br /><a href="/w/index.php?title=Dicyanoether&action=edit&redlink=1" class="new" title="Dicyanoether (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">O(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Cyanogen_fluoride" title="Cyanogen fluoride">FCN</a>
</td>
<td>Ne
</td></tr>
<tr style="background-color:mistyrose">
<td><a href="/wiki/Sodium_cyanide" title="Sodium cyanide">NaCN</a>
</td>
<td><a href="/wiki/Magnesium_cyanide" title="Magnesium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Mg(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Aluminium_cyanide" title="Aluminium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Al(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Silicon_tetracyanide&action=edit&redlink=1" class="new" title="Silicon tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Si(CN)<sub class="template-chem2-sub">4</sub></span></a><br /><a href="/wiki/Trimethylsilyl_cyanide" title="Trimethylsilyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">3</sub>SiCN</span></a>
</td>
<td><a href="/wiki/Phosphorus_tricyanide" title="Phosphorus tricyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">P(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/wiki/Thiocyanate" title="Thiocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/wiki/Isothiocyanate" title="Isothiocyanate">-NCS</a><br /><a href="/wiki/Thiocyanogen" title="Thiocyanogen"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Sulfur_dicyanide" title="Sulfur dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">S(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Cyanogen_chloride" title="Cyanogen chloride">ClCN</a>
</td>
<td>Ar
</td></tr>
<tr style="background-color:mistyrose">
<td><a href="/wiki/Potassium_cyanide" title="Potassium cyanide">KCN</a>
</td>
<td><a href="/wiki/Calcium_cyanide" title="Calcium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ca(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td style="background-color:white;border:none">
</td>
<td><a href="/w/index.php?title=Scandium_cyanide&action=edit&redlink=1" class="new" title="Scandium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sc(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Ti
</td>
<td>V
</td>
<td><a href="/wiki/Potassium_hexacyanochromate(III)" title="Potassium hexacyanochromate(III)">Cr(CN)<sub>6</sub><sup>3−</sup></a>
</td>
<td>Mn
</td>
<td><a href="/wiki/Iron(II)_cyanide" title="Iron(II) cyanide">Fe(CN)<sub>2</sub></a><br /><a href="/wiki/Ferrocyanide" title="Ferrocyanide">Fe(CN)<sub>6</sub><sup>4−</sup></a><br /><a href="/wiki/Ferricyanide" title="Ferricyanide">Fe(CN)<sub>6</sub><sup>3−</sup></a>
</td>
<td><a href="/wiki/Cobalt(II)_cyanide" title="Cobalt(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Co(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Pentacyanocobaltate" title="Pentacyanocobaltate">Co(CN)<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">5</sub></span></span></a>
</td>
<td><a href="/wiki/Nickel_dicyanide" title="Nickel dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ni(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Cyanonickelate" title="Cyanonickelate">Ni(CN)<sub>4</sub><sup>2−</sup></a><br /><a href="/w/index.php?title=Cyanonickelate(0)&action=edit&redlink=1" class="new" title="Cyanonickelate(0) (page does not exist)">Ni(CN)<sub>4</sub><sup>4−</sup></a>
</td>
<td><a href="/wiki/Copper(I)_cyanide" title="Copper(I) cyanide">CuCN</a>
</td>
<td><a href="/wiki/Zinc_cyanide" title="Zinc cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Zn(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Gallium(III)_cyanide" title="Gallium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ga(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Germanium_dicyanide&action=edit&redlink=1" class="new" title="Germanium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Germanium_tetracyanide&action=edit&redlink=1" class="new" title="Germanium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ge(CN)<sub class="template-chem2-sub">4</sub></span></a>
</td>
<td><a href="/w/index.php?title=Arsenic_tricyanide&action=edit&redlink=1" class="new" title="Arsenic tricyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">As(CN)<sub class="template-chem2-sub">3</sub></span></a><br /><a href="/wiki/Cacodyl_cyanide" title="Cacodyl cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(CH<sub class="template-chem2-sub">3</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a><br /><a href="/wiki/Diphenylcyanoarsine" title="Diphenylcyanoarsine"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(C<sub class="template-chem2-sub">6</sub>H<sub class="template-chem2-sub">5</sub>)<sub class="template-chem2-sub">2</sub>AsCN</span></a>
</td>
<td><a href="/wiki/Selenocyanate" title="Selenocyanate"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">SeCN<sup class="template-chem2-sup">−</sup></span></a><br /><a href="/w/index.php?title=Selenocyanogen&action=edit&redlink=1" class="new" title="Selenocyanogen (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">(SeCN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Selenium_dicyanide&action=edit&redlink=1" class="new" title="Selenium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Se(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Cyanogen_bromide" title="Cyanogen bromide">BrCN</a>
</td>
<td>Kr
</td></tr>
<tr style="background-color:mistyrose">
<td><a href="/wiki/Rubidium_cyanide" title="Rubidium cyanide">RbCN</a>
</td>
<td><a href="/w/index.php?title=Strontium_cyanide&action=edit&redlink=1" class="new" title="Strontium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sr(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td style="background-color:white;border:none">
</td>
<td><a href="/w/index.php?title=Yttrium_cyanide&action=edit&redlink=1" class="new" title="Yttrium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Y(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Zr
</td>
<td>Nb
</td>
<td><a href="/wiki/Potassium_octacyanomolybdate(IV)" title="Potassium octacyanomolybdate(IV)">Mo(CN)<sub>8</sub><sup>4−</sup></a>
</td>
<td>Tc
</td>
<td>Ru
</td>
<td>Rh
</td>
<td><a href="/wiki/Palladium_dicyanide" title="Palladium dicyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pd(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/wiki/Silver_cyanide" title="Silver cyanide">AgCN</a>
</td>
<td><a href="/wiki/Cadmium_cyanide" title="Cadmium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Cd(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/w/index.php?title=Indium_cyanide&action=edit&redlink=1" class="new" title="Indium cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">In(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Tin(II)_cyanide&action=edit&redlink=1" class="new" title="Tin(II) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sn(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/w/index.php?title=Antimony_cyanide&action=edit&redlink=1" class="new" title="Antimony cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sb(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Tellurium_dicyanide&action=edit&redlink=1" class="new" title="Tellurium dicyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/w/index.php?title=Tellurium_tetracyanide&action=edit&redlink=1" class="new" title="Tellurium tetracyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Te(CN)<sub class="template-chem2-sub">4</sub></span></a>
</td>
<td><a href="/wiki/Cyanogen_iodide" title="Cyanogen iodide">ICN</a>
</td>
<td>Xe
</td></tr>
<tr style="background-color:mistyrose">
<td><a href="/wiki/Caesium_cyanide" title="Caesium cyanide">CsCN</a>
</td>
<td><a href="/wiki/Barium_cyanide" title="Barium cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ba(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td style="background-color:white;border:none">*
</td>
<td><a href="/w/index.php?title=Lutetium(III)_cyanide&action=edit&redlink=1" class="new" title="Lutetium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Lu(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Hf
</td>
<td>Ta
</td>
<td><a href="/w/index.php?title=Potassium_octacyanotungstate(IV)&action=edit&redlink=1" class="new" title="Potassium octacyanotungstate(IV) (page does not exist)">W(CN)<sub>8</sub><sup>4−</sup></a>
</td>
<td>Re
</td>
<td>Os
</td>
<td>Ir
</td>
<td><a href="/wiki/Platinocyanide" title="Platinocyanide">Pt(CN)<sub>4</sub><sup>2-</sup></a><br /><a href="/w/index.php?title=Platinicyanide&action=edit&redlink=1" class="new" title="Platinicyanide (page does not exist)">Pt(CN)<sub>6</sub><sup>4-</sup></a><br />
</td>
<td><a href="/wiki/Gold(I)_cyanide" title="Gold(I) cyanide">AuCN</a><br /><a href="/wiki/Potassium_dicyanoaurate" title="Potassium dicyanoaurate">Au(CN)<sub>2</sub><sup>-</sup></a>
</td>
<td><a href="/w/index.php?title=Mercury(I)_cyanide&action=edit&redlink=1" class="new" title="Mercury(I) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg<sub class="template-chem2-sub">2</sub>(CN)<sub class="template-chem2-sub">2</sub></span></a><br /><a href="/wiki/Mercury(II)_cyanide" title="Mercury(II) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Hg(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/w/index.php?title=Thallium(I)_cyanide&action=edit&redlink=1" class="new" title="Thallium(I) cyanide (page does not exist)">TlCN</a>
</td>
<td><a href="/w/index.php?title=Lead_cyanide&action=edit&redlink=1" class="new" title="Lead cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pb(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td><a href="/w/index.php?title=Bismuth(III)_cyanide&action=edit&redlink=1" class="new" title="Bismuth(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Bi(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Po
</td>
<td>At
</td>
<td>Rn
</td></tr>
<tr style="background-color:mistyrose">
<td>Fr
</td>
<td>Ra
</td>
<td style="background-color:white;border:none">**
</td>
<td>Lr
</td>
<td>Rf
</td>
<td>Db
</td>
<td>Sg
</td>
<td>Bh
</td>
<td>Hs
</td>
<td>Mt
</td>
<td>Ds
</td>
<td>Rg
</td>
<td>Cn
</td>
<td>Nh
</td>
<td>Fl
</td>
<td>Mc
</td>
<td>Lv
</td>
<td>Ts
</td>
<td>Og
</td></tr>
<tr>
<td style="background-color:white;border:none" colspan="2" rowspan="3">
</td>
<td style="background-color:white;border:none" colspan="20"> 
</td></tr>
<tr style="background-color:mistyrose">
<td style="background-color:white;border:none">*
</td>
<td><a href="/w/index.php?title=Lanthanum_cyanide&action=edit&redlink=1" class="new" title="Lanthanum cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">La(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Cerium(III)_cyanide&action=edit&redlink=1" class="new" title="Cerium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">3</sub></span></a><br /> <a href="/w/index.php?title=Cerium(IV)_cyanide&action=edit&redlink=1" class="new" title="Cerium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ce(CN)<sub class="template-chem2-sub">4</sub></span></a>
</td>
<td><a href="/w/index.php?title=Praseodymium(III)_cyanide&action=edit&redlink=1" class="new" title="Praseodymium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Pr(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Nd
</td>
<td>Pm
</td>
<td><a href="/w/index.php?title=Samarium(III)_cyanide&action=edit&redlink=1" class="new" title="Samarium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Sm(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Europium(III)_cyanide&action=edit&redlink=1" class="new" title="Europium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Eu(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Gadolinium(III)_cyanide&action=edit&redlink=1" class="new" title="Gadolinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Gd(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Tb
</td>
<td><a href="/w/index.php?title=Dysprosium(III)_cyanide&action=edit&redlink=1" class="new" title="Dysprosium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Dy(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Holmium(III)_cyanide&action=edit&redlink=1" class="new" title="Holmium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ho(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td>Er
</td>
<td>Tm
</td>
<td><a href="/wiki/Ytterbium(III)_cyanide" title="Ytterbium(III) cyanide"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Yb(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td></tr>
<tr style="background-color:mistyrose">
<td style="background-color:white;border:none">**
</td>
<td><a href="/w/index.php?title=Actinium(III)_cyanide&action=edit&redlink=1" class="new" title="Actinium(III) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Ac(CN)<sub class="template-chem2-sub">3</sub></span></a>
</td>
<td><a href="/w/index.php?title=Thorium(IV)_cyanide&action=edit&redlink=1" class="new" title="Thorium(IV) cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">Th(CN)<sub class="template-chem2-sub">4</sub></span></a>
</td>
<td>Pa
</td>
<td><a href="/w/index.php?title=Uranyl_cyanide&action=edit&redlink=1" class="new" title="Uranyl cyanide (page does not exist)"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1123817410"><span class="chemf nowrap">UO<sub class="template-chem2-sub">2</sub>(CN)<sub class="template-chem2-sub">2</sub></span></a>
</td>
<td>Np
</td>
<td>Pu
</td>
<td>Am
</td>
<td>Cm
</td>
<td>Bk
</td>
<td>Cf
</td>
<td>Es
</td>
<td>Fm
</td>
<td>Md
</td>
<td>No
</td></tr></tbody></table></div>
</div></td></tr></tbody></table></div>
<div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1228936124"></div><div role="navigation" class="navbox" aria-labelledby="Inorganic_compounds_of_carbon_and_related_ions" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1063604349"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Inorganic_compounds_of_carbon" title="Template:Inorganic compounds of carbon"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Inorganic_compounds_of_carbon" title="Template talk:Inorganic compounds of carbon"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Inorganic_compounds_of_carbon" title="Special:EditPage/Template:Inorganic compounds of carbon"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Inorganic_compounds_of_carbon_and_related_ions" style="font-size:114%;margin:0 4em"><a href="/wiki/List_of_inorganic_compounds" title="List of inorganic compounds">Inorganic compounds of</a> <a href="/wiki/Carbon" title="Carbon">carbon</a> and related ions</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Compounds</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Carbon_monofluoride" title="Carbon monofluoride">CF</a></li>
<li><a href="/wiki/Carbon_monoxide" title="Carbon monoxide">CO</a></li>
<li><a href="/wiki/Carbon_dioxide" title="Carbon dioxide">CO<sub>2</sub></a></li>
<li><a href="/wiki/Carbon_trioxide" title="Carbon trioxide">CO<sub>3</sub></a></li>
<li><a href="/wiki/Carbon_tetroxide" title="Carbon tetroxide">CO<sub>4</sub></a></li>
<li><a href="/wiki/Carbon_pentoxide" title="Carbon pentoxide">CO<sub>5</sub></a></li>
<li><a href="/wiki/Carbon_hexoxide" title="Carbon hexoxide">CO<sub>6</sub></a></li>
<li><a href="/wiki/Carbonyl_sulfide" title="Carbonyl sulfide">COS</a></li>
<li><a href="/wiki/Carbon_monosulfide" title="Carbon monosulfide">CS</a></li>
<li><a href="/wiki/Ethenedithione" title="Ethenedithione">C<sub>2</sub>S<sub>2</sub></a></li>
<li><a href="/wiki/Carbon_disulfide" title="Carbon disulfide">CS<sub>2</sub></a></li>
<li><a href="/wiki/Carbon_diselenide" title="Carbon diselenide">CSe<sub>2</sub></a></li>
<li><a href="/wiki/Carbon_suboxide" title="Carbon suboxide">C<sub>3</sub>O<sub>2</sub></a></li>
<li><a href="/wiki/Carbon_subsulfide" title="Carbon subsulfide">C<sub>3</sub>S<sub>2</sub></a></li>
<li><a href="/wiki/Silicon_carbide" title="Silicon carbide">SiC</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Carbon ions</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Carbide" title="Carbide">Carbides</a> [:C≡C:]<sup>2−</sup>, [::C::]<sup>4−</sup>, [:C=C=C:]<sup>4−</sup></li>
<li><a class="mw-selflink selflink">Cyanide</a> [:C≡N:]<sup>−</sup></li>
<li><a href="/wiki/Cyanate" title="Cyanate">Cyanate</a> [:O−C≡N:]<sup>−</sup></li>
<li><a href="/wiki/Thiocyanate" title="Thiocyanate">Thiocyanate</a> [:S−C≡N:]<sup>−</sup></li>
<li><a href="/wiki/Fulminate" title="Fulminate">Fulminate</a> [:C≡N−O:]<sup>−</sup></li>
<li><a href="https://www.wikidata.org/wiki/Q27110079" class="extiw" title="wikidata:Q27110079">Thiofulminate</a> [:C≡N−S:]<sup>−</sup></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Nanostructures</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Graphite_intercalation_compounds" class="mw-redirect" title="Graphite intercalation compounds">Graphite intercalation compounds</a></li>
<li><a href="/wiki/Fulleride" title="Fulleride">Fullerides</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Oxides and related</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Oxocarbon" title="Oxocarbon">Oxides</a></li>
<li><a href="/wiki/Carbon_nitride" title="Carbon nitride">Nitrides</a></li>
<li><a href="/wiki/Metal_carbonyl" title="Metal carbonyl">Metal carbonyls</a></li>
<li><a href="/wiki/Carbonic_acid" title="Carbonic acid">Carbonic acid</a></li>
<li><a href="/wiki/Bicarbonate" title="Bicarbonate">Bicarbonates</a></li>
<li><a href="/wiki/Carbonate" title="Carbonate">Carbonates</a></li></ul>
</div></td></tr></tbody></table></div>
<div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1228936124"></div><div role="navigation" class="navbox" aria-labelledby="Nitrogen_species" style="padding:3px"><table class="nowraplinks mw-collapsible mw-collapsed navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1063604349"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Nitrogen_compounds" title="Template:Nitrogen compounds"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Nitrogen_compounds" title="Template talk:Nitrogen compounds"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Nitrogen_compounds" title="Special:EditPage/Template:Nitrogen compounds"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Nitrogen_species" style="font-size:114%;margin:0 4em"><a href="/wiki/Nitrogen" title="Nitrogen">Nitrogen</a> species</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Hydrides</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Ammonia" title="Ammonia">NH<sub>3</sub></a></li>
<li><a href="/wiki/Ammonium" title="Ammonium">NH<sub>4</sub><sup>+</sup></a></li>
<li><a href="/wiki/Metal_amides#Alkali_metal_amides" title="Metal amides">NH<sub>2</sub><sup>−</sup></a></li>
<li><a href="/wiki/Nitride" title="Nitride">N<sup>3−</sup></a></li>
<li><a href="/wiki/Hydroxylamine" title="Hydroxylamine">NH<sub>2</sub>OH</a></li>
<li><a href="/wiki/Hydrazine" title="Hydrazine">N<sub>2</sub>H<sub>4</sub></a></li>
<li><a href="/wiki/Hydrazoic_acid" title="Hydrazoic acid">HN<sub>3</sub></a></li>
<li><a href="/wiki/Azide" title="Azide">N<sub>3</sub><sup>−</sup></a></li>
<li><a href="/wiki/Nitrogen_pentahydride" title="Nitrogen pentahydride"><i>NH<sub>5</sub></i></a> (?)</li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Organic</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Amine" title="Amine">NR<sub>3</sub></a></li>
<li><a href="/wiki/Imine" title="Imine">>C=NR</a></li>
<li><a href="/wiki/Amide" title="Amide">-CONR<sub>2</sub></a></li>
<li><a href="/wiki/Nitrile" title="Nitrile">-CN</a></li>
<li><a href="/wiki/Hydrogen_cyanide" title="Hydrogen cyanide">HCN</a></li>
<li><a class="mw-selflink selflink">CN<sup>−</sup></a></li>
<li><a href="/wiki/Cyanogen" title="Cyanogen">(CN)<sub>2</sub></a></li>
<li><a href="/wiki/Cyanamide" title="Cyanamide">H<sub>2</sub>NCN</a></li>
<li><a href="/wiki/Cyanate" title="Cyanate">HOCN</a></li>
<li><a href="/wiki/Isocyanate" title="Isocyanate">HNCO</a></li>
<li><a href="/wiki/Isothiocyanate" title="Isothiocyanate">HNCS</a></li>
<li><a href="/wiki/Diazomethane" title="Diazomethane">CH<sub>2</sub>N<sub>2</sub></a></li>
<li><a href="/wiki/Nitroso" title="Nitroso">-NO</a></li>
<li><a href="/wiki/Nitro_compound" title="Nitro compound">-NO<sub>2</sub></a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Nitrogen_oxide" title="Nitrogen oxide">Oxides</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Nitric_oxide" title="Nitric oxide">NO</a> / <a href="/wiki/Dinitrogen_dioxide" title="Dinitrogen dioxide">(NO)<sub>2</sub></a></li>
<li><a href="/wiki/Dinitrogen_trioxide" title="Dinitrogen trioxide">N<sub>2</sub>O<sub>3</sub></a></li>
<li><a href="/wiki/Nitrous_acid" title="Nitrous acid">HNO<sub>2</sub></a> / <a href="/wiki/Nitrite" title="Nitrite">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrosonium" title="Nitrosonium">NO<sup>+</sup></a></li>
<li><a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">NO<sub>2</sub></a> / <a href="/wiki/Dinitrogen_tetroxide" title="Dinitrogen tetroxide">(NO<sub>2</sub>)<sub>2</sub></a></li>
<li><a href="/wiki/Dinitrogen_pentoxide" title="Dinitrogen pentoxide">N<sub>2</sub>O<sub>5</sub></a></li>
<li><a href="/wiki/Nitric_acid" title="Nitric acid">HNO<sub>3</sub></a> / <a href="/wiki/Nitrate" title="Nitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a> / <a href="/wiki/Nitronium" class="mw-redirect" title="Nitronium">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">+</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a></li>
<li><a href="/wiki/Nitrate_radical" title="Nitrate radical">NO<sub>3</sub></a></li>
<li><a href="/wiki/Nitroxyl" title="Nitroxyl">HNO</a> / <a href="/wiki/Hyponitrous_acid" title="Hyponitrous acid">(HON)<sub>2</sub></a> / <a href="/wiki/Hyponitrite" title="Hyponitrite">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">2</sub></span></span></a> / <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">N<sub>2</sub>O</a></li>
<li><a href="/wiki/Nitramide" title="Nitramide">H<sub>2</sub>NNO<sub>2</sub></a></li>
<li><a href="/wiki/Peroxynitrous_acid" title="Peroxynitrous acid">HO<sub>2</sub>NO</a> / <a href="/wiki/Peroxynitrite" title="Peroxynitrite">ONOO<sup>−</sup></a></li>
<li><a href="/wiki/Peroxynitric_acid" title="Peroxynitric acid">HO<sub>2</sub>NO<sub>2</sub></a> / <a href="/wiki/Peroxynitrate" title="Peroxynitrate">O<sub>2</sub>NOO<sup>−</sup></a></li>
<li><a href="/wiki/Orthonitrate" title="Orthonitrate">NO<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">3−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">4</sub></span></span></a></li>
<li><a href="/wiki/Nitroxylic_acid" title="Nitroxylic acid">H<sub>4</sub>N<sub>2</sub>O<sub>4</sub></a> / <a href="/wiki/Angeli%27s_salt" title="Angeli's salt">N<sub>2</sub>O<span class="nowrap"><span style="display:inline-block;margin-bottom:-0.3em;vertical-align:-0.4em;line-height:1.2em;font-size:80%;text-align:left"><sup style="font-size:inherit;line-height:inherit;vertical-align:baseline">2−</sup><br /><sub style="font-size:inherit;line-height:inherit;vertical-align:baseline">3</sub></span></span></a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Halides</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Nitrogen_monofluoride" title="Nitrogen monofluoride">NF</a></li>
<li><a href="/wiki/Nitrogen_difluoride" title="Nitrogen difluoride">NF<sub>2</sub></a></li>
<li><a href="/wiki/Nitrogen_trifluoride" title="Nitrogen trifluoride">NF<sub>3</sub></a></li>
<li><a href="/wiki/Nitrogen_pentafluoride" title="Nitrogen pentafluoride"><i>NF<sub>5</sub></i></a> (?)</li>
<li><a href="/wiki/Nitrogen_trichloride" title="Nitrogen trichloride">NCl<sub>3</sub></a></li>
<li><a href="/wiki/Nitrogen_tribromide" title="Nitrogen tribromide">NBr<sub>3</sub></a></li>
<li><a href="/wiki/Nitrogen_triiodide" title="Nitrogen triiodide">NI<sub>3</sub></a></li>
<li><a href="/wiki/Fluorine_azide" title="Fluorine azide">FN<sub>3</sub></a></li>
<li><a href="/wiki/Chlorine_azide" title="Chlorine azide">ClN<sub>3</sub></a></li>
<li><a href="/wiki/Bromine_azide" title="Bromine azide">BrN<sub>3</sub></a></li>
<li><a href="/wiki/Iodine_azide" title="Iodine azide">IN<sub>3</sub></a></li>
<li><a href="/wiki/Fluoroamine" title="Fluoroamine">NH<sub>2</sub>F</a></li>
<li><a href="/wiki/Dinitrogen_difluoride" title="Dinitrogen difluoride">N<sub>2</sub>F<sub>2</sub></a></li>
<li><a href="/wiki/Monochloramine" title="Monochloramine">NH<sub>2</sub>Cl</a></li>
<li><a href="/w/index.php?title=Difluoramine&action=edit&redlink=1" class="new" title="Difluoramine (page does not exist)">NHF<sub>2</sub></a></li>
<li><a href="/wiki/Dichloramine" title="Dichloramine">NHCl<sub>2</sub></a></li>
<li><a href="/w/index.php?title=Dibromamine&action=edit&redlink=1" class="new" title="Dibromamine (page does not exist)">NHBr<sub>2</sub></a></li>
<li><a href="/w/index.php?title=Diiodoamine&action=edit&redlink=1" class="new" title="Diiodoamine (page does not exist)">NHI<sub>2</sub></a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Oxidation_state" title="Oxidation state">Oxidation states</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><span style="font-size:112%;"><b><a href="/wiki/Nitride" title="Nitride">−3</a></b></span>, <a href="/wiki/Hydrazine" title="Hydrazine">−2</a>, <a href="/wiki/Hydroxylamine" title="Hydroxylamine">−1</a>, 0, <a href="/wiki/Nitroxyl" title="Nitroxyl">+1</a>, <a href="/wiki/Nitric_oxide" title="Nitric oxide">+2</a>, <span style="font-size:112%;"><b><a href="/wiki/Nitrite" title="Nitrite">+3</a></b></span>, <a href="/wiki/Nitrogen_dioxide" title="Nitrogen dioxide">+4</a>,
<span style="font-size:112%;"><b><a href="/wiki/Nitrate" title="Nitrate">+5</a></b></span> (a strongly <a href="/wiki/Acid" title="Acid">acidic</a> oxide)</div></td></tr></tbody></table></div>
<div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1228936124"></div><div role="navigation" class="navbox" aria-labelledby="Pest_control:_Rodenticides" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1063604349"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Rodenticides" title="Template:Rodenticides"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Rodenticides" title="Template talk:Rodenticides"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Rodenticides" title="Special:EditPage/Template:Rodenticides"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Pest_control:_Rodenticides" style="font-size:114%;margin:0 4em"><a href="/wiki/Pest_control" title="Pest control">Pest control</a>: <a href="/wiki/Rodenticide" title="Rodenticide">Rodenticides</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;;line-height:1.2em;"><a href="/wiki/Anticoagulant" title="Anticoagulant">Anticoagulants</a> /<br /><a href="/wiki/Vitamin_K_antagonist" title="Vitamin K antagonist">Vitamin K antagonists</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/Coumarin" title="Coumarin">Coumarins</a> /<br /><a href="/wiki/4-Hydroxycoumarins" title="4-Hydroxycoumarins">4-Hydroxycoumarins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">1st generation</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Warfarin" title="Warfarin">Warfarin</a></li>
<li><a href="/wiki/Coumatetralyl" title="Coumatetralyl">Coumatetralyl</a></li>
<li><a href="/wiki/Fumarin" title="Fumarin">Fumarin</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;font-size:smaller;">2nd generation (<a href="/wiki/Superwarfarin" title="Superwarfarin">Superwarfarins</a>)</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Brodifacoum" title="Brodifacoum">Brodifacoum</a></li>
<li><a href="/wiki/Bromadiolone" title="Bromadiolone">Bromadiolone</a></li>
<li><a href="/wiki/Difenacoum" title="Difenacoum">Difenacoum</a></li>
<li><a href="/wiki/Difethialone" title="Difethialone">Difethialone</a></li>
<li><a href="/wiki/Flocoumafen" title="Flocoumafen">Flocoumafen</a></li></ul>
</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;line-height:1.2em;font-weight:normal;"><a href="/wiki/1,3-Indandione" title="1,3-Indandione">1,3-Indandiones</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Chlorophacinone" title="Chlorophacinone">Chlorophacinone</a></li>
<li><a href="/wiki/Pindone" title="Pindone">Pindone</a></li>
<li><a href="/wiki/Diphacinone" class="mw-redirect" title="Diphacinone">Diphacinone</a></li></ul>
</div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Convulsant" title="Convulsant">Convulsants</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li>
<li><a href="/wiki/Phenylsilatrane" title="Phenylsilatrane">Phenylsilatrane</a></li>
<li><a href="/wiki/Strychnine" title="Strychnine">Strychnine</a></li>
<li><a href="/wiki/Tetramethylenedisulfotetramine" title="Tetramethylenedisulfotetramine">Tetramethylenedisulfotetramine</a></li>
<li><a href="/wiki/Chlorophenylsilatrane" title="Chlorophenylsilatrane">Chlorophenylsilatrane</a></li>
<li><a href="/wiki/RDX" title="RDX">RDX</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Vitamin_D" title="Vitamin D">Calciferols</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a></li>
<li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Inorganic_compound" title="Inorganic compound">Inorganic compounds</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Aluminium_phosphide" title="Aluminium phosphide">Aluminium phosphide</a></li>
<li><a href="/wiki/Arsenic" title="Arsenic">Arsenic</a></li>
<li><a href="/wiki/Barium_carbonate" title="Barium carbonate">Barium carbonate</a></li>
<li><a href="/wiki/Calcium_phosphide" title="Calcium phosphide">Calcium phosphide</a></li>
<li><a class="mw-selflink selflink">Cyanide</a></li>
<li><a href="/wiki/Thallium(I)_sulfate" title="Thallium(I) sulfate">Thallium sulfate</a></li>
<li><a href="/wiki/Zinc_phosphide" title="Zinc phosphide">Zinc phosphide</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organochlorine" class="mw-redirect" title="Organochlorine">Organochlorine</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Chloralose" title="Chloralose">Chloralose</a></li>
<li><a href="/wiki/Endrin" title="Endrin">Endrin</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Organophosphorus" class="mw-redirect" title="Organophosphorus">Organophosphorus</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;"><a href="/wiki/Carbamate" title="Carbamate">Carbamates</a></th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li>
<li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;background:powderblue;">Others</th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Alpha-Naphthylthiourea" class="mw-redirect" title="Alpha-Naphthylthiourea">α-Naphthylthiourea</a></li>
<li><a href="/wiki/Bromethalin" title="Bromethalin">Bromethalin</a></li>
<li><a href="/wiki/Fluoroacetamide" title="Fluoroacetamide">Fluoroacetamide</a></li>
<li><a href="/wiki/Flupropadine" title="Flupropadine">Flupropadine</a></li>
<li><a href="/wiki/1,3-Difluoro-2-propanol" title="1,3-Difluoro-2-propanol">1,3-Difluoro-2-propanol (Gliftor)</a></li>
<li><a href="/wiki/Norbormide" title="Norbormide">Norbormide</a></li>
<li><a href="/wiki/Pyrinuron" title="Pyrinuron">Pyrinuron</a></li>
<li><a href="/wiki/Scilliroside" title="Scilliroside">Scilliroside</a></li>
<li><a href="/wiki/Sodium_fluoroacetate" title="Sodium fluoroacetate">Sodium fluoroacetate</a></li></ul>
</div></td></tr></tbody></table></div>
<div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1228936124"></div><div role="navigation" class="navbox" aria-labelledby="Consumer_food_safety" style="padding:3px"><table class="nowraplinks hlist mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1063604349"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Consumer_food_safety" title="Template:Consumer food safety"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Consumer_food_safety" title="Template talk:Consumer food safety"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Consumer_food_safety" title="Special:EditPage/Template:Consumer food safety"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Consumer_food_safety" style="font-size:114%;margin:0 4em"><a href="/wiki/Food_safety" title="Food safety">Consumer food safety</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Adulterant" title="Adulterant">Adulterants</a>, <a href="/wiki/Food_contaminant" title="Food contaminant">food contaminants</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/3-MCPD" title="3-MCPD">3-MCPD</a></li>
<li><a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li>
<li><a href="/wiki/Antibiotic_use_in_livestock" title="Antibiotic use in livestock">Antibiotic use in livestock</a></li>
<li><a class="mw-selflink selflink">Cyanide</a></li>
<li><a href="/wiki/Formaldehyde" title="Formaldehyde">Formaldehyde</a></li>
<li><a href="/wiki/HGH_controversies" title="HGH controversies">HGH controversies</a></li>
<li><a href="/wiki/Lead_poisoning" title="Lead poisoning">Lead poisoning</a></li>
<li><a href="/wiki/Melamine" title="Melamine">Melamine</a></li>
<li><a href="/wiki/Mercury_in_fish" title="Mercury in fish">Mercury in fish</a></li>
<li><a href="/wiki/Sudan_I" title="Sudan I">Sudan I</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_additive" title="Food additive">Food additives</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Flavoring" title="Flavoring">Flavorings</a></li>
<li><a href="/wiki/Monosodium_glutamate" title="Monosodium glutamate">Monosodium glutamate (MSG)</a></li>
<li><a href="/wiki/Sodium_chloride" title="Sodium chloride">Salt</a></li>
<li><a href="/wiki/Sugar" title="Sugar">Sugar</a>
<ul><li><a href="/wiki/High-fructose_corn_syrup" title="High-fructose corn syrup">High-fructose corn syrup</a></li></ul></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Intestinal_parasite_infection" title="Intestinal parasite infection">Intestinal parasites</a>, <a href="/wiki/Parasitic_disease" title="Parasitic disease">parasitic disease</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Amoebiasis" title="Amoebiasis">Amoebiasis</a></li>
<li><a href="/wiki/Anisakiasis" class="mw-redirect" title="Anisakiasis">Anisakiasis</a></li>
<li><a href="/wiki/Cryptosporidiosis" title="Cryptosporidiosis">Cryptosporidiosis</a></li>
<li><a href="/wiki/Cyclosporiasis" title="Cyclosporiasis">Cyclosporiasis</a></li>
<li><a href="/wiki/Diphyllobothriasis" title="Diphyllobothriasis">Diphyllobothriasis</a></li>
<li><a href="/wiki/Pinworm_infection" title="Pinworm infection">Enterobiasis</a></li>
<li><a href="/wiki/Fasciolopsiasis" title="Fasciolopsiasis">Fasciolopsiasis</a></li>
<li><a href="/wiki/Fasciolosis" title="Fasciolosis">Fasciolosis</a></li>
<li><a href="/wiki/Giardiasis" title="Giardiasis">Giardiasis</a></li>
<li><a href="/wiki/Gnathostomiasis" title="Gnathostomiasis">Gnathostomiasis</a></li>
<li><a href="/wiki/Paragonimiasis" title="Paragonimiasis">Paragonimiasis</a></li>
<li><a href="/wiki/Toxocariasis" title="Toxocariasis">Toxocariasis</a></li>
<li><a href="/wiki/Toxoplasmosis" title="Toxoplasmosis">Toxoplasmosis</a></li>
<li><a href="/wiki/Trichinosis" title="Trichinosis">Trichinosis</a></li>
<li><a href="/wiki/Trichuriasis" title="Trichuriasis">Trichuriasis</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Microorganism" title="Microorganism">Microorganisms</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Botulism" title="Botulism">Botulism</a></li>
<li><i><a href="/wiki/Campylobacter_jejuni" title="Campylobacter jejuni">Campylobacter jejuni</a></i></li>
<li><i><a href="/wiki/Clostridium_perfringens" title="Clostridium perfringens">Clostridium perfringens</a></i></li>
<li><i><a href="/wiki/Cronobacter" title="Cronobacter">Cronobacter</a></i></li>
<li><i><a href="/wiki/Enterovirus" title="Enterovirus">Enterovirus</a></i></li>
<li><a href="/wiki/Escherichia_coli_O104:H4" title="Escherichia coli O104:H4"><i>Escherichia coli</i> O104:H4</a></li>
<li><a href="/wiki/Escherichia_coli_O157:H7" title="Escherichia coli O157:H7"><i>Escherichia coli</i> O157:H7</a></li>
<li><a href="/wiki/Hepatitis_A" title="Hepatitis A">Hepatitis A</a></li>
<li><a href="/wiki/Hepatitis_E" title="Hepatitis E">Hepatitis E</a></li>
<li><i><a href="/wiki/Listeria" title="Listeria">Listeria</a></i></li>
<li><a href="/wiki/Norovirus" title="Norovirus">Norovirus</a></li>
<li><a href="/wiki/Rotavirus" title="Rotavirus">Rotavirus</a></li>
<li><i><a href="/wiki/Salmonella" title="Salmonella">Salmonella</a></i></li>
<li><a href="/wiki/Shigatoxigenic_and_verotoxigenic_Escherichia_coli" title="Shigatoxigenic and verotoxigenic Escherichia coli">Shigatoxigenic and verotoxigenic <i>E. coli</i></a></li>
<li><i><a href="/wiki/Vibrio_cholerae" title="Vibrio cholerae">Vibrio cholerae</a></i></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Pesticide" title="Pesticide">Pesticides</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li>
<li><a href="/wiki/DDT" title="DDT">DDT</a></li>
<li><a href="/wiki/Lindane" title="Lindane">Lindane</a></li>
<li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li>
<li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Preservative" title="Preservative">Preservatives</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic acid</a></li>
<li><a href="/wiki/Ethylenediaminetetraacetic_acid" title="Ethylenediaminetetraacetic acid">Ethylenediaminetetraacetic acid (EDTA)</a></li>
<li><a href="/wiki/Sodium_benzoate" title="Sodium benzoate">Sodium benzoate</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Sugar_substitute" title="Sugar substitute">Sugar substitutes</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Acesulfame_potassium" title="Acesulfame potassium">Acesulfame potassium</a></li>
<li><a href="/wiki/Aspartame" title="Aspartame">Aspartame</a>
<ul><li><a href="/wiki/Aspartame_controversy" title="Aspartame controversy">controversy</a></li></ul></li>
<li><a href="/wiki/Saccharin" title="Saccharin">Saccharin</a></li>
<li><a href="/wiki/Sodium_cyclamate" class="mw-redirect" title="Sodium cyclamate">Sodium cyclamate</a></li>
<li><a href="/wiki/Sorbitol" title="Sorbitol">Sorbitol</a></li>
<li><a href="/wiki/Sucralose" title="Sucralose">Sucralose</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Toxin" title="Toxin">Toxins</a>, <a href="/wiki/Poison" title="Poison">poisons</a>, <a href="/wiki/Pollution" title="Pollution">environment pollution</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Aflatoxin" title="Aflatoxin">Aflatoxin</a></li>
<li><a href="/wiki/Arsenic_contamination_of_groundwater" title="Arsenic contamination of groundwater">Arsenic contamination of groundwater</a></li>
<li><a href="/wiki/Benzene_in_soft_drinks" title="Benzene in soft drinks">Benzene in soft drinks</a></li>
<li><a href="/wiki/Bisphenol_A" title="Bisphenol A">Bisphenol A</a></li>
<li><a href="/wiki/Dieldrin" title="Dieldrin">Dieldrin</a></li>
<li><a href="/wiki/Diethylstilbestrol" title="Diethylstilbestrol">Diethylstilbestrol</a></li>
<li><a href="/wiki/Dioxin" title="Dioxin">Dioxin</a></li>
<li><a href="/wiki/Mycotoxin" title="Mycotoxin">Mycotoxins</a></li>
<li><a href="/wiki/Nonylphenol" title="Nonylphenol">Nonylphenol</a></li>
<li><a href="/wiki/Shellfish_poisoning" title="Shellfish poisoning">Shellfish poisoning</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_fraud" class="mw-redirect" title="Food fraud">Food fraud</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Bread_fraud" class="mw-redirect" title="Bread fraud">Bread</a></li>
<li><a href="/wiki/Breast_milk_fraud" class="mw-redirect" title="Breast milk fraud">Breast milk</a></li>
<li><a href="/wiki/Egg_fraud" class="mw-redirect" title="Egg fraud">Egg</a></li>
<li><a href="/wiki/Olive_oil_fraud" class="mw-redirect" title="Olive oil fraud">Olive oil</a></li>
<li><a href="/wiki/Prawn_fraud" class="mw-redirect" title="Prawn fraud">Prawn</a></li>
<li><a href="/wiki/Seafood_fraud" class="mw-redirect" title="Seafood fraud">Seafood</a></li>
<li><a href="/wiki/Shrimp_fraud" class="mw-redirect" title="Shrimp fraud">Shrimp</a></li>
<li><a href="/wiki/Tea_fraud" class="mw-redirect" title="Tea fraud">Tea</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Food_processing" title="Food processing">Food processing</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/4-Hydroxynonenal" title="4-Hydroxynonenal">4-Hydroxynonenal</a></li>
<li><a href="/wiki/Acid-hydrolyzed_vegetable_protein" class="mw-redirect" title="Acid-hydrolyzed vegetable protein">Acid-hydrolyzed vegetable protein</a></li>
<li><a href="/wiki/Acrylamide" title="Acrylamide">Acrylamide</a></li>
<li><a href="/wiki/Creutzfeldt%E2%80%93Jakob_disease" title="Creutzfeldt–Jakob disease">Creutzfeldt–Jakob disease</a></li>
<li><a href="/wiki/List_of_food_additives" title="List of food additives">Food additives</a></li>
<li><a href="/wiki/Food_irradiation" title="Food irradiation">Food irradiation</a></li>
<li><a href="/wiki/Heterocyclic_amine" title="Heterocyclic amine">Heterocyclic amines</a></li>
<li><a href="/wiki/Modified_starch" title="Modified starch">Modified starch</a></li>
<li><a href="/wiki/Nitrosamine" title="Nitrosamine">Nitrosamines</a></li>
<li><a href="/wiki/Polycyclic_aromatic_hydrocarbon" title="Polycyclic aromatic hydrocarbon">Polycyclic aromatic hydrocarbon</a></li>
<li><a href="/wiki/Shortening" title="Shortening">Shortening</a></li>
<li><a href="/wiki/Trans_fat" title="Trans fat">Trans fat</a></li>
<li><a href="/wiki/Water_fluoridation_controversy" title="Water fluoridation controversy">Water fluoridation controversy</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_contamination_incidents" title="List of food contamination incidents">Food contamination incidents</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Devon_colic" title="Devon colic">Devon colic</a></li>
<li><a href="/wiki/Swill_milk_scandal" title="Swill milk scandal">Swill milk scandal</a></li>
<li><a href="/wiki/Esing_Bakery_incident" title="Esing Bakery incident">Esing Bakery incident</a></li>
<li><a href="/wiki/1858_Bradford_sweets_poisoning" title="1858 Bradford sweets poisoning">1858 Bradford sweets poisoning</a></li>
<li><a href="/wiki/1900_English_beer_poisoning" title="1900 English beer poisoning">1900 English beer poisoning</a></li>
<li><a href="/wiki/Morinaga_Milk_arsenic_poisoning_incident" title="Morinaga Milk arsenic poisoning incident">Morinaga Milk arsenic poisoning incident</a></li>
<li><a href="/wiki/Minamata_disease" title="Minamata disease">Minamata disease</a></li>
<li><a href="/wiki/1971_Iraq_poison_grain_disaster" title="1971 Iraq poison grain disaster">1971 Iraq poison grain disaster</a></li>
<li><a href="/wiki/Toxic_oil_syndrome" title="Toxic oil syndrome">Toxic oil syndrome</a></li>
<li><a href="/wiki/1985_Austrian_diethylene_glycol_wine_scandal" title="1985 Austrian diethylene glycol wine scandal">1985 Austrian diethylene glycol wine scandal</a></li>
<li><a href="/wiki/United_Kingdom_BSE_outbreak" title="United Kingdom BSE outbreak">United Kingdom BSE outbreak</a></li>
<li><a href="/wiki/Australian_meat_substitution_scandal" title="Australian meat substitution scandal">Australian meat substitution scandal</a></li>
<li><a href="/wiki/1993_Jack_in_the_Box_E._coli_outbreak" class="mw-redirect" title="1993 Jack in the Box E. coli outbreak">Jack in the Box <i>E. coli</i> outbreak</a></li>
<li><a href="/wiki/1996_Odwalla_E._coli_outbreak" title="1996 Odwalla E. coli outbreak">1996 Odwalla <i>E. coli</i> outbreak</a></li>
<li><a href="/wiki/2006_North_American_E._coli_O157:H7_outbreaks" title="2006 North American E. coli O157:H7 outbreaks">2006 North American <i>E. coli</i> outbreaks</a></li>
<li><a href="/wiki/ICA_meat_repackaging_controversy" title="ICA meat repackaging controversy">ICA meat repackaging controversy</a></li>
<li><a href="/wiki/2008_Canada_listeriosis_outbreak" title="2008 Canada listeriosis outbreak">2008 Canada listeriosis outbreak</a></li>
<li><a href="/wiki/2008_Chinese_milk_scandal" title="2008 Chinese milk scandal">2008 Chinese milk scandal</a></li>
<li><a href="/wiki/2008_Irish_pork_crisis" title="2008 Irish pork crisis">2008 Irish pork crisis</a></li>
<li><a href="/wiki/2008_United_States_salmonellosis_outbreak" title="2008 United States salmonellosis outbreak">2008 United States salmonellosis outbreak</a></li>
<li><a href="/wiki/2011_Germany_E._coli_O104:H4_outbreak" title="2011 Germany E. coli O104:H4 outbreak">2011 Germany <i>E. coli</i> outbreak</a></li>
<li><a href="/wiki/2011_United_States_listeriosis_outbreak" title="2011 United States listeriosis outbreak">2011 United States listeriosis outbreak</a></li>
<li><a href="/wiki/Bihar_school_meal_poisoning_incident" title="Bihar school meal poisoning incident">Bihar school meal poisoning</a></li>
<li><a href="/wiki/2013_horse_meat_scandal" title="2013 horse meat scandal">2013 horse meat scandal</a></li>
<li><a href="/wiki/Mozambique_funeral_beer_poisoning" title="Mozambique funeral beer poisoning">2015 Mozambique funeral beer poisoning</a></li>
<li><a href="/wiki/Operation_Weak_Meat" title="Operation Weak Meat">2017 Brazil Operation Weak Meat</a></li>
<li><a href="/wiki/2017%E2%80%932018_South_African_listeriosis_outbreak" title="2017–2018 South African listeriosis outbreak">2017–2018 South African listeriosis outbreak</a></li>
<li><a href="/wiki/2018_Australian_strawberry_contamination" title="2018 Australian strawberry contamination">2018 Australian strawberry contamination</a></li>
<li><a href="/wiki/2024_United_Kingdom_Shigatoxigenic_E._coli_outbreak" title="2024 United Kingdom Shigatoxigenic E. coli outbreak">2024 United Kingdom Shigatoxigenic E. coli outbreak</a></li>
<li><a href="/wiki/Kobayashi_red_yeast_rice_scandal" title="Kobayashi red yeast rice scandal">Kobayashi red yeast rice scandal</a></li>
<li><a href="/wiki/Food_safety_incidents_in_China" title="Food safety incidents in China">Food safety incidents in China</a></li>
<li><a href="/wiki/Food_safety_incidents_in_Taiwan" title="Food safety incidents in Taiwan">Food safety incidents in Taiwan</a></li>
<li><a href="/wiki/Foodborne_illness" title="Foodborne illness">Foodborne illness</a>
<ul><li><a href="/wiki/List_of_foodborne_illness_outbreaks" title="List of foodborne illness outbreaks">outbreaks</a></li>
<li><a href="/wiki/List_of_foodborne_illness_outbreaks_by_death_toll" title="List of foodborne illness outbreaks by death toll">death toll</a></li>
<li><a href="/wiki/List_of_foodborne_illness_outbreaks_in_the_United_States" title="List of foodborne illness outbreaks in the United States">United States</a></li></ul></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Regulation" title="Regulation">Regulation</a>, <a href="/wiki/Standards_organization" title="Standards organization">standards</a>, <a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">watchdogs</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Acceptable_daily_intake" title="Acceptable daily intake">Acceptable daily intake</a></li>
<li><a href="/wiki/E_number" title="E number">E number</a></li>
<li><a href="/wiki/List_of_food_labeling_regulations" title="List of food labeling regulations">Food labeling regulations</a></li>
<li><a href="/wiki/Food_libel_laws" title="Food libel laws">Food libel laws</a></li>
<li><a href="/wiki/Food_safety_in_Australia" title="Food safety in Australia">Food safety in Australia</a></li>
<li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li>
<li><a href="/wiki/ISO_22000" title="ISO 22000">ISO 22000</a></li>
<li><a href="/wiki/Nutrition_facts_label" title="Nutrition facts label">Nutrition facts label</a></li>
<li><a href="/wiki/Organic_certification" title="Organic certification">Organic certification</a></li>
<li><a href="/wiki/Quality_Assurance_International" title="Quality Assurance International">Quality Assurance International</a></li>
<li><a href="/wiki/United_Kingdom_food_information_regulations" title="United Kingdom food information regulations">United Kingdom food information regulations</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/List_of_food_safety_organisations" title="List of food safety organisations">Institutions</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Centre_for_Food_Safety" title="Centre for Food Safety">Centre for Food Safety</a> (Hong Kong)</li>
<li><a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a></li>
<li><a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a></li>
<li><a href="/wiki/Food_Information_and_Control_Agency" title="Food Information and Control Agency">Food Information and Control Agency</a> (Spain)</li>
<li><a href="/wiki/Food_Standards_Agency" title="Food Standards Agency">Food Standards Agency</a> (United Kingdom)</li>
<li><a href="/wiki/Institute_for_Food_Safety_and_Health" title="Institute for Food Safety and Health">Institute for Food Safety and Health</a></li>
<li><a href="/wiki/International_Food_Safety_Network" title="International Food Safety Network">International Food Safety Network</a></li>
<li><a href="/wiki/Ministry_of_Food_and_Drug_Safety" title="Ministry of Food and Drug Safety">Ministry of Food and Drug Safety</a> (South Korea)</li>
<li><a href="/wiki/Spanish_Agency_for_Food_Safety_and_Nutrition" title="Spanish Agency for Food Safety and Nutrition">Spanish Agency for Food Safety and Nutrition</a></li></ul>
</div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Related topics</th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><a href="/wiki/Curing_(food_preservation)" title="Curing (food preservation)">Curing (food preservation)</a></li>
<li><a href="/wiki/Food_and_drink_prohibitions" title="Food and drink prohibitions">Food and drink prohibitions</a></li>
<li><a href="/wiki/Food_marketing" title="Food marketing">Food marketing</a></li>
<li><a href="/wiki/Food_politics" title="Food politics">Food politics</a></li>
<li><a href="/wiki/Food_preservation" title="Food preservation">Food preservation</a></li>
<li><a href="/wiki/Food_quality" title="Food quality">Food quality</a></li>
<li><a href="/wiki/Genetically_modified_food" title="Genetically modified food">Genetically modified food</a></li>
<li><a href="/wiki/Conspiracy_theories" class="mw-redirect" title="Conspiracy theories">Conspiracy theories</a></li></ul>
</div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="font-weight:bold;"><div>
<ul><li><span class="nowrap"><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Foodlogo2.svg" class="mw-file-description"><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/16px-Foodlogo2.svg.png" decoding="async" width="16" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/24px-Foodlogo2.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Foodlogo2.svg/32px-Foodlogo2.svg.png 2x" data-file-width="146" data-file-height="106" /></a></span> </span><a href="/wiki/Portal:Food" title="Portal:Food">Food portal</a> <span class="nowrap"><span class="noviewer" typeof="mw:File"><span><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/9px-Goblet_Glass_%28Banquet%29.svg.png" decoding="async" width="9" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/14px-Goblet_Glass_%28Banquet%29.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e2/Goblet_Glass_%28Banquet%29.svg/19px-Goblet_Glass_%28Banquet%29.svg.png 2x" data-file-width="239" data-file-height="408" /></span></span> </span><a href="/wiki/Portal:Drink" title="Portal:Drink">Drink portal</a></li>
<li><span class="noviewer" typeof="mw:File"><span title="Category"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/16px-Symbol_category_class.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/23px-Symbol_category_class.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/96/Symbol_category_class.svg/31px-Symbol_category_class.svg.png 2x" data-file-width="180" data-file-height="185" /></span></span> <a href="/wiki/Category:Food_safety" title="Category:Food safety">Category</a></li>
<li><span class="noviewer" typeof="mw:File"><span title="Commons page"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/12px-Commons-logo.svg.png" decoding="async" width="12" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/18px-Commons-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/4/4a/Commons-logo.svg/24px-Commons-logo.svg.png 2x" data-file-width="1024" data-file-height="1376" /></span></span> <a href="https://commons.wikimedia.org/wiki/Category:Food_safety" class="extiw" title="commons:Category:Food safety">Commons</a></li>
<li><span class="noviewer" typeof="mw:File"><a href="/wiki/File:Wikibooks-logo.svg" class="mw-file-description" title="Wikibooks page"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/16px-Wikibooks-logo.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/24px-Wikibooks-logo.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/fa/Wikibooks-logo.svg/32px-Wikibooks-logo.svg.png 2x" data-file-width="300" data-file-height="300" /></a></span> <a href="https://en.wikibooks.org/wiki/Cookbook" class="extiw" title="wikibooks:Cookbook">Cookbook</a></li>
<li><span class="noviewer" typeof="mw:File"><span title="WikiProject"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/16px-People_icon.svg.png" decoding="async" width="16" height="16" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/24px-People_icon.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/People_icon.svg/32px-People_icon.svg.png 2x" data-file-width="100" data-file-height="100" /></span></span> <a href="/wiki/Wikipedia:WikiProject_Food_and_drink" title="Wikipedia:WikiProject Food and drink">WikiProject</a></li></ul>
</div></td></tr></tbody></table></div>
<div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1228936124"><style data-mw-deduplicate="TemplateStyles:r1038841319">.mw-parser-output .tooltip-dotted{border-bottom:1px dotted;cursor:help}</style></div><div role="navigation" class="navbox authority-control" aria-label="Navbox" style="padding:3px"><table class="nowraplinks hlist navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Help:Authority_control" title="Help:Authority control">Authority control databases</a>: National <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q55076544#identifiers" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em">
<ul><li><span class="uid"><a rel="nofollow" class="external text" href="https://d-nb.info/gnd/4148424-1">Germany</a></span></li>
<li><span class="uid"><a rel="nofollow" class="external text" href="http://olduli.nli.org.il/F/?func=find-b&local_base=NLX10&find_code=UID&request=987007538319905171">Israel</a></span></li>
<li><span class="uid"><a rel="nofollow" class="external text" href="https://id.loc.gov/authorities/sh85035028">United States</a></span></li>
<li><span class="uid"><a rel="nofollow" class="external text" href="https://id.ndl.go.jp/auth/ndlna/00570870">Japan</a></span></li>
<li><span class="uid"><span class="rt-commentedText tooltip tooltip-dotted" title="kyanidy"><a rel="nofollow" class="external text" href="https://aleph.nkp.cz/F/?func=find-c&local_base=aut&ccl_term=ica=ph273306&CON_LNG=ENG">Czech Republic</a></span></span></li></ul>
</div></td></tr></tbody></table></div></div>' |
Whether or not the change was made through a Tor exit node (tor_exit_node ) | false |
Unix timestamp of change (timestamp ) | '1720326941' |