Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 16:13, 21 February 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits Undid revision 415142404 by 84.241.6.63 (talk) = soman is not sarin← Previous edit		Latest revision as of 13:08, 12 December 2024 edit undo14.139.206.206 (talk)No edit summary
Line 1:		Line 1:
			{{Short description|Chemical compound and chemical warfare nerve agent}}
			{{CS1 config|name-list-style=vanc}}
	{{Other uses}}		{{Other uses}}
			{{Distinguish|serine|sarrin|Saran (disambiguation){{!}}saran}}
	{{chembox
			{{Use mdy dates|date=July 2023}}
			{{Chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 409172515		| verifiedrevid = 415149010
	| Reference=<ref>{{cite web|publisher=United States Senate|work=103d Congress, 2d Session|date=May 25, 1994|url=http://www.gulfweb.org/bigdoc/report/appgb.html|title=Material Safety Data Sheet -- Lethal Nerve Agent Sarin (GB)|accessdate=2004-11-06}}</ref>		| Reference = <ref>{{cite web |publisher=United States Senate |work=103d Congress, 2d Session |date=May 25, 1994 |title=Material Safety Data Sheet – Lethal Nerve Agent Sarin (GB) |url=http://www.gulfweb.org/bigdoc/report/appgb.html |access-date=November 6, 2004}}</ref>
	| Name = Sarin		| Name = Sarin
			| pronounce = {{IPAc-en|ˈ|s|ɑː|r|ɪ|n}}
	| ImageFileL1 = Sarin-skeletal.png
			| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageSizeL1 = 130px
	| ImageFileR1 = Sarin-3D-balls.png		| ImageFile = Sarin-2D-by-AHRLS-2011.png
			| ImageFile1 = Sarin-3D-balls-by-AHRLS-2012.png
	| ImageSizeR1 = 120px
			| ImageName1 = ''S''-Sarin
	| PIN = propan-2-yl methylphosphonofluoridate
			| PIN = Propan-2-yl methylphosphonofluoridate
	| OtherNames = ''O''-isopropyl methylphosphonofluoridate, Isopropyl, GB methylphosphonofluoridate<br>GB<ref>http://webbook.nist.gov/cgi/cbook.cgi?Name=sarin&Units=SI&cMS=on</ref><br>2-(Fluoro-methylphosphoryl)oxypropane
			| SystematicName =
			| OtherNames = (''RS'')-''O''-Isopropyl methylphosphonofluoridate; IMPF;<br>GB;<ref>{{cite web |title=Sarin |publisher=] |url=https://webbook.nist.gov/cgi/cbook.cgi?Name=sarin&Units=SI&cMS=on |access-date=March 27, 2011}}</ref><br>2-(Fluoro-methylphosphoryl)oxypropane;<br>Phosphonofluoridic acid, ''P''-methyl-, 1-methylethyl ester<br>EA-1208<br>TL-1618<br>T-144
			| IUPACName =
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7583		| ChemSpiderID = 7583
	| InChI1 = 1/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3		| InChI1 = 1/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3
	| InChIKey1 = DYAHQFWOVKZOOW-UHFFFAOYAY		| InChIKey1 = DYAHQFWOVKZOOW-UHFFFAOYAY
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 75701
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 509554		| ChEMBL = 509554
Line 24:		Line 35:
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 107-44-8		| CASNo = 107-44-8
	| PubChem = 7871		| PubChem = 7871
			| UNII_Ref = {{fdacite|changed|FDA}}
	| SMILES = FP(=O)(OC(C)C)C
			| UNII = B4XG72QGFM
	| InChI=1/C4H10FO2P/c1-4<br/>(2)7-8(3,5)6/h4H,1-3H3
			| SMILES = FP(=O)(OC(C)C)C
	}}
			| InChI=1/C4H10FO2P/c1-4(2)7-8(3,5)6/h4H,1-3H3
			}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| C=4 | H=10 | F=1 | O=2 | P=1
	| Formula = C<sub>4</sub>H<sub>10</sub>FO<sub>2</sub>P
			| Appearance = Clear colourless liquid, brownish if impure
	| MolarMass = 140.09 g/mol
			| Odor = Odourless in pure form. Impure sarin can smell like mustard or burned rubber.
	| Appearance = Clear colorless liquid. Odorless in pure form.
	| BoilingPtC = 158		| BoilingPtC = 158
	| MeltingPtC = -56		| MeltingPtC = -56
	| Solubility = miscible		| Solubility = Miscible
	| Density = 1.0887 g/cm³ at 25 °C<br>1.102 g/cm³ at 20 °C		| Density = 1.0887 g/cm<sup>3</sup> (25&nbsp;°C)<br>1.102 g/cm<sup>3</sup> (20&nbsp;°C)
	}}		| LogP = 0.30
			}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
			| ExternalSDS =
	| ExternalMSDS =
			| LD50 = 39 μg/kg (intravenous, rat)<ref name="Substance Name: Sarin">{{cite web |title=Substance Name: Sarin |website=ChemIDplus |publisher=U.S. National Library of Medicine, National Institutes of Health |language=en |url=https://pubchem.ncbi.nlm.nih.gov/compound/7871 |access-date=January 19, 2020}}</ref>
	| EUClass = Extremely Toxic ('''T+'''), Corrosive (C)
			| MainHazards = Extremely lethal ] agent.
	| NFPA-H = 4
	| NFPA-F = 1		| NFPA-H = 4
	| NFPA-R = 0		| NFPA-F = 1
	}}		| NFPA-R = 1
			| IDLH = 0.1 mg/m<sup>3</sup>
			| TLV-STEL = 0.0001 mg/m<sup>3</sup>
			| TLV-TWA = 0.00003 mg/m<sup>3</sup>
			| FlashPtC =
			| GHSPictograms = {{GHS skull and crossbones}}
			| GHSSignalWord =
			}}
			| Section4 =
			| Section5 =
			| Section6 =
	}}		}}
			'''Sarin''' (] designation '''GB''' ], "B"]) is an extremely toxic ].<ref name=niosh>. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. Accessed April 20, 2009.</ref> A colourless, odourless ], it is used as a ] due to its extreme potency as a ]. Exposure can be lethal even at very low concentrations, where death can occur within one to ten minutes after direct inhalation of a lethal dose,<ref>{{cite report |last=Anderson |first=Kenneth |work=Lawfare: Hard National Security Choices |date=September 17, 2013 |title=A Poisonous Affair: America, Iraq, and the Gassing of Halabja review of A Poisonous Affair: America, Iraq, and the Gassing of Halabja by Joost R. Hiltermann (Cambridge UP 2007) |url=https://www.lawfaremedia.org/article/poisonous-affair-america-iraq-and-gassing-halabja-joost-r-hiltermann |access-date=December 30, 2015 |quote=... death can occur within one minute of direct inhalation as the lung muscles are paralyzed.}}</ref><ref>{{cite news |last=Smith |first=Michael |date=August 26, 2002 |title=Saddam to be target of Britain's 'E-bomb' |work=] |page=A18 |url=https://www.telegraph.co.uk/news/worldnews/middleeast/iraq/1405440/Saddam-to-be-target-of-Britains-E-bomb.html |access-date=December 30, 2015 |quote=The nerve agents sarin and VX. Colourless and tasteless, they cause death by respiratory arrest in one to 15 minutes.}}</ref> due to suffocation from respiratory paralysis, unless antidotes are quickly administered.<ref name=niosh/> People who absorb a non-lethal dose and do not receive immediate medical treatment may suffer permanent neurological damage.{{Citation needed|date=July 2022}}
	'''Sarin''', or '''GB''' is an ] with the formula CH<sub>3</sub>P(O)F. It is a colorless, odorless liquid,<ref name=niosh>. Emergency Response Safety and Health Database. National Institute for Occupational Safety and Health. Accessed April 20, 2009.</ref> which is used as a ]. It has been classified as a ] in ]. Production and stockpiling of sarin was outlawed by the ] of 1993 where it is classified as a ].
			Sarin is widely considered a ]. Production and stockpiling of sarin was outlawed as of April 1997 by the ] of 1993, and it is classified as a ].
			==Health effects==
			]{{Broader|Organophosphate poisoning}}
			Like some other nerve agents that affect the ] ], sarin attacks the ] by interfering with the degradation of the neurotransmitter acetylcholine at ]s. Death usually occurs as a result of ] due to the inability to control the muscles involved in breathing.<ref name=":1">{{cite book |last=Vohra |first=Rais |title=Poisoning & Drug Overdose |publisher=McGraw Hill |year=2022 |edition=8th |language=English |chapter=Organophosphorus and carbamate insecticides}}</ref>
			Initial symptoms following exposure to sarin are a ], tightness in the chest, and ] (miotic action). Soon after, the person will have difficulty breathing and experience ] and drooling. This progresses to losing control of bodily functions, which may cause the person to vomit, defecate, and urinate. This phase is followed by ] and jerking. Ultimately, the person becomes comatose and suffocates in a series of convulsive ]s. Common mnemonics for the symptomatology of organophosphate poisoning, including sarin, are the "killer Bs" of ] and ] because they are the leading cause of death,<ref>{{cite journal |last=Gussow |first=Leon |title=Nerve Agents: Three Mechanisms, Three Antidotes |journal=Emergency Medicine News |publisher=] |location=Alphen aan den Rijn, Netherlands |volume=27 |issue=7 |page=12 |date=July 2005 |doi=10.1097/00132981-200507000-00011}}</ref> and ] – salivation, ], urination, defecation, gastrointestinal distress, and emesis (vomiting). Death may follow in one to ten minutes after direct inhalation, but may also occur after a delay ranging from hours to several weeks, in cases where exposure is limited but no antidote is applied.<ref name=":1"/>
			Sarin has a high ] (ease with which a liquid can turn into vapour) relative to similar nerve agents, making inhalation very easy, and may even absorb through the skin. A person's clothing can release sarin for about 30 minutes after it has come in contact with sarin gas, which can lead to exposure of other people.<ref name="CDC">{{cite web |title=Facts About Sarin |publisher=] |date=November 18, 2015 |url=https://www.cdc.gov/chemicalemergencies/factsheets/sarin.html |access-date=March 20, 2024}}</ref>
			===Management===
			Treatment measures have been described.<ref name=CDC/> Treatment is typically with the ]s ] and ].<ref name=niosh/> Atropine, an ] to ]s, is given to treat the physiological symptoms of poisoning. Since muscular response to acetylcholine is mediated through ]s, atropine does not counteract the muscular symptoms. Pralidoxime can regenerate ]s if administered within approximately five hours. ], a synthetic ], has been suggested as an alternative to atropine due to its better ] penetration and higher efficacy.<ref>{{cite journal |last=Shim |first=TM |author2=McDonough JH |title=Efficacy of biperiden and atropine as anticonvulsant treatment for organophosphorus nerve agent intoxication |journal=Archives of Toxicology |date=May 2000 |volume=74 |issue=3 |pages=165–172 |pmid=10877003 |s2cid=13749842 |doi=10.1007/s002040050670 |bibcode=2000ArTox..74..165S |url=https://apps.dtic.mil/sti/pdfs/ADA385192.pdf |access-date=April 29, 2018 |url-status=live |archive-url=https://web.archive.org/web/20170923164236/http://www.dtic.mil/get-tr-doc/pdf?AD=ADA385192 |archive-date=September 23, 2017}}</ref>
			===Mechanism of action===
			Sarin is a potent ],<ref>{{cite journal |vauthors=Abu-Qare AW, Abou-Donia MB |title=Sarin: health effects, metabolism, and methods of analysis |journal=] |publisher=] |location=Amsterdam, Netherlands |volume=40 |issue=10 |pages=1327–33 |date=October 2002 |pmid=12387297 |doi=10.1016/S0278-6915(02)00079-0}}</ref> an enzyme that degrades the ] ] after it is released into the ]. In vertebrates, acetylcholine is the neurotransmitter used at the neuromuscular junction, where signals are transmitted between ]s from the ] to muscle fibres. Normally, acetylcholine is released from the neuron to stimulate the muscle, after which it is degraded by ], allowing the muscle to relax. A build-up of acetylcholine in the ], due to the inhibition of acetylcholinesterase, means the neurotransmitter continues to act on the muscle fibre, so that any nerve impulses are effectively continually transmitted.
			Sarin acts on acetylcholinesterase by forming a ] with the particular ] residue at the active site. Fluoride is the ], and the resulting organo-phosphoester is robust and ].<ref>{{cite journal |vauthors=Millard CB, Kryger G, Ordentlich A, etal |title=Crystal Structures of Aged Phosphonylated Acetylcholinesterase: Nerve Agent Reaction Products at the Atomic Level |journal=Biochemistry |volume=38 |issue=22 |pages=7032–9 |date=June 1999 |pmid=10353814 |s2cid=11744952 |doi=10.1021/bi982678l}}. See {{Proteopedia|1cfj}}.</ref><ref>{{cite journal |last1=Hörnberg |first1=Andreas |last2=Tunemalm |first2=Anna-Karin |last3=Ekström |first3=Fredrik |title=Crystal Structures of Acetylcholinesterase in Complex with Organophosphorus Compounds Suggest that the Acyl Pocket Modulates the Aging Reaction by Precluding the Formation of the Trigonal Bipyramidal Transition State |journal=Biochemistry |volume=46 |issue=16 |pages=4815–4825 |year=2007 |pmid=17402711 |doi=10.1021/bi0621361}}</ref>
			Its mechanism of action resembles that of some commonly used ]s, such as ]. In terms of biological activity, it resembles ] insecticides, such as ], and the medicines ], ], and ].
			===Diagnostic tests===
			Controlled studies in healthy men have shown that a nontoxic 0.43&nbsp;mg oral dose administered in several portions over a 3-day interval caused average maximum depressions of 22 and 30%, respectively, in plasma and erythrocyte acetylcholinesterase levels. A single acute 0.5&nbsp;mg dose caused mild symptoms of intoxication and an average reduction of 38% in both measures of acetylcholinesterase activity. Sarin in blood is rapidly degraded either ''in vivo'' or ''in vitro''. Its primary inactive ]s have ''in vivo'' serum half-lives of approximately 24 hours. The serum level of unbound isopropyl methylphosphonic acid (IMPA), a sarin ] product, ranged from 2–135&nbsp;μg/L in survivors of a terrorist attack during the first four hours post-exposure. Sarin or its metabolites may be determined in blood or urine by gas or liquid ], while acetylcholinesterase activity is usually measured by enzymatic methods.<ref>{{cite book |last1=Baselt |first1=Randall C. |last2=Cravey |first2=Robert H. |title=Disposition of Toxic Drugs and Chemicals in Man |publisher=Biomedical Publications |location=Seal Beach, California |date=2017 |isbn=978-0-8151-0547-3 |pages=1926–1928 |url=https://archive.org/details/dispositionoftox00base |url-access=registration}}</ref>
			A newer method called "fluoride regeneration" or "fluoride reactivation" detects the presence of nerve agents for a longer period after exposure than the methods described above. Fluoride reactivation is a technique that has been explored since at least the early 2000s. This technique obviates some of the deficiencies of older procedures. Sarin not only reacts with the water in the blood plasma through hydrolysis (forming so-called 'free metabolites'), but also reacts with various proteins to form 'protein adducts'. These protein adducts are not so easily removed from the body, and remain for a longer period of time than the free metabolites. One clear advantage of this process is that the period, post-exposure, for determination of sarin exposure is much longer, possibly five to eight weeks according to at least one study.<ref>{{cite report |title=Fluoride Ion Regeneration of Sarin (GB) from Minipig Tissue and Fluids Following Whole-Body GB Vapor Exposure |date=July 2003 |publisher=United States Army |last=Jakubowski |display-authors=etal |url=https://apps.dtic.mil/sti/tr/pdf/ADA484093.pdf |access-date=March 20, 2024 |url-status=live |archive-url=https://web.archive.org/web/20160102095524/http://www.dtic.mil/dtic/tr/fulltext/u2/a484093.pdf |archive-date=January 2, 2016}}</ref><ref>{{cite journal |title=Improvements of the Fluoride Reactivation Method for the Verification of Nerve Agent Exposure |last=Degenhardt |display-authors=etal |date=July 2004 |journal=] |publisher=] |location=Oxfordshire, England |volume=28 |issue=5 |pages=364–371 |pmid=15239857 |doi=10.1093/jat/28.5.364 |doi-access=free}}</ref>
			===Toxicity===
			As a nerve gas, sarin in its purest form is estimated to be 26 times more deadly than ].<ref>{{cite web |title=Sarin gas as chemical agent – ThinkQuest- Library |url=http://library.thinkquest.org/27393/dreamwvr/agents/sarin1.htm |access-date=August 13, 2007 |url-status=dead |archive-url=https://web.archive.org/web/20070808094319/http://library.thinkquest.org/27393/dreamwvr/agents/sarin1.htm |archive-date=August 8, 2007}}</ref> The ] of ] sarin in mice is 172 μg/kg.<ref>{{cite journal |last=Inns |first=RH |author2=NJ Tuckwell |author3=JE Bright |author4=TC Marrs |title=Histochemical Demonstration of Calcium Accumulation in Muscle Fibres after Experimental Organophosphate Poisoning |journal=Hum Exp Toxicol |date=July 1990 |volume=9 |issue=4 |pages=245–250 |pmid=2390321 |bibcode=1990HETox...9..245I |s2cid=20713579 |doi=10.1177/096032719000900407}}</ref>
			Sarin is highly toxic, whether by contact with the skin or breathed in. The toxicity of sarin in humans is largely based on calculations from studies with animals. The lethal concentration of sarin in air is approximately 28–35&nbsp;mg per cubic meter per minute for a two-minute exposure time by a healthy adult breathing normally (exchanging 15 liters of air per minute, lower 28 mg/m<sup>3</sup> value is for general population).<ref>{{cite book |title=Chemical Warfare Agents: Biomedical and Psychological Effects, Medical Countermeasures, and Emergency Response |last1=Lukey |first1=Brian J. |last2=Romano |first2=James A. Jr. |last3=Salem |first3=Harry |date=April 11, 2019 |publisher=CRC Press |isbn=978-0-429-63296-9 |language=en |url=https://books.google.com/books?id=DQqWDwAAQBAJ&q=exponent+lethality+vx&pg=PA174}}</ref> This number represents the estimated lethal concentration for 50% of exposed victims, the ] value. The ] or ] value is estimated to be 40–83 mg per cubic meter for exposure time of two minutes.<ref>{{cite book |title=Review of Acute Human-Toxicity Estimates for GB (Sarin) |last=Toxicology |first=National Research Council (US) Committee on |date=1997 |publisher=National Academies Press (US) |language=en |url=https://www.ncbi.nlm.nih.gov/books/NBK233733/}}</ref><ref>{{cite journal |last1=Bide |first1=R. W. |last2=Armour |first2=S. J. |last3=Yee |first3=E. |date=2005 |title=GB toxicity reassessed using newer techniques for estimation of human toxicity from animal inhalation toxicity data: new method for estimating acute human toxicity (GB) |journal=Journal of Applied Toxicology |volume=25 |issue=5 |pages=393–409 |issn=0260-437X |pmid=16092087 |s2cid=8769521 |doi=10.1002/jat.1074}}</ref> Calculating effects for different exposure times and concentrations requires following specific toxic load models. In general, brief exposures to higher concentrations are more lethal than comparable long time exposures to low concentrations.<ref>{{cite book |title=Chemical Warfare Agents: Biomedical and Psychological Effects, Medical Countermeasures, and Emergency Response |last1=Lukey |first1=Brian J. |last2=Romano |first2=James A. Jr. |last3=Salem |first3=Harry |date=April 11, 2019 |publisher=CRC Press |isbn=978-0-429-63296-9 |language=en |url=https://books.google.com/books?id=DQqWDwAAQBAJ&q=exponent+lethality+vx&pg=PA171}}</ref> There are many ways to make relative comparisons between toxic substances. The list below compares sarin to some current and historic chemical warfare agents, with a direct comparison to the respiratory LCt<sub>50</sub>:
			* ], 2,860&nbsp;mg/(min·m<sup>3</sup>)<ref name=":0">{{cite book |title=US Army Field Manual 3–11.9 Potential Military Chemical/Biological Agents and Compounds |publisher=United States Department of Defense |year=2005}}</ref> – Sarin is 81 times more lethal
			* ], 1,500&nbsp;mg/(min·m<sup>3</sup>)<ref name=":0"/> – Sarin is 43 times more lethal
			* ], 1,000&nbsp;mg/(min·m<sup>3</sup>)<ref name=":0"/> – Sarin is 28 times more lethal
			* ], 19,000&nbsp;mg/(min·m<sup>3</sup>)<ref>{{cite book |title=US Army Field Manual 3–9 Potential Military Chemical/Biological Agents and Compounds |publisher=United States Department of Defense |year=1990 |pages=71}}</ref> – Sarin is 543 times more lethal
	==Production and structure==		==Production and structure==
			Sarin is a ] molecule because it has four chemically distinct ] attached to the ] phosphorus center.<ref>{{cite book |last=Corbridge |first=D. E. C. |title=Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology |publisher=] |location=Amsterdam, Netherlands |date=1995 |isbn=0-444-89307-5}}</ref> The ''S<sub>P</sub> ''form (the ]) is the more active ] due to its greater ] to ].<ref name=enantiomers1>{{cite journal |last1=Kovarik |first1=Zrinka |last2=Radić |first2=Zoran |last3=Berman |first3=Harvey A. |last4=Simeon-Rudolf |first4=Vera |last5=Reiner |first5=Elsa |last6=Taylor |first6=Palmer |title=Acetylcholinesterase active centre and gorge conformations analysed by combinatorial mutations and enantiomeric phosphonates |journal=] |publisher=] |location=London, England |date=March 2003 |volume=373 |pages=33–40 |pmid=12665427 |issue=Pt. 1 |pmc=1223469 |doi=10.1042/BJ20021862}}</ref><ref name=enantiomers2>{{cite journal |title=Nerve agent stereoisomers: analysis, isolation and toxicology |last1=Benschop |first1=H. P. |last2=De Jong |first2=L. P. A. |journal=] |publisher=] |location=Washington DC |date=1988 |volume=21 |issue=10 |pages=368–374 |doi=10.1021/ar00154a003}}</ref> The P-F bond is easily broken by ] agents, such as water and hydroxide. At high ], sarin decomposes rapidly to nontoxic ] derivatives.<ref name=FAS/>
	Sarin is a ], with four ] attached to the ].<ref>D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam 1995. ISBN 0-444-89307-5.</ref> It is prepared from ] and a mixture of ].
	:CH<sub>3</sub>P(O)F<sub>2</sub> + (CH<sub>3</sub>)<sub>2</sub>CHOH → CH<sub>3</sub>P(O)F + HF
			It is almost always manufactured as a ] (a 1:1 mixture of its enantiomeric forms) as this involves a much simpler ] while providing an adequate weapon.<ref name=enantiomers1/><ref name=enantiomers2/>
	] is added to neutralize the ] generated during this ] reaction. As a ], it can be generated ] by this same reaction.
			A number of production pathways can be used to create sarin. The final reaction typically involves attachment of the isopropoxy group to the phosphorus with an ] with ]. Two variants of this final step are common. One is the reaction of ] with isopropyl alcohol, which produces a racemic mixture of sarin enantiomers with ] as a byproduct:<ref name=FAS/>
	==Biological effects==
	{{Confusing|section|date=July 2010}}
	]. (photo 1970)]]
	Its ] resembles that of some commonly used ]s, such as ]. In terms of biological activity, it resembles ] insecticides such as ] and ]s ], ], and ]. Like other nerve agents, sarin attacks the ].
			:]
	Specifically, sarin is a potent ] of the enzyme ].<ref>{{cite journal |author=Abu-Qare AW, Abou-Donia MB |title=Sarin: health effects, metabolism, and methods of analysis |journal=Food Chem. Toxicol. |volume=40 |issue=10 |pages=1327–33 |year=2002 |month=October |pmid=12387297 |doi=10.1016/S0278-6915(02)00079-0 |url=}}</ref> Sarin acts on cholinesterase by forming a ] with the particular ] residue at the active site. Fluoride is the leaving group, and the resulting ] is robust but biologically inactive.<ref>{{cite journal |author=Millard CB, Kryger G, Ordentlich A, ''et al.'' |title=Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level |journal=Biochemistry |volume=38 |issue=22 |pages=7032–9 |year=1999 |month=June |pmid=10353814 |doi=10.1021/bi982678l |url=}}. See {{Proteopedia|1cfj}}.</ref><ref>{{cite web|title=Structure of acetylcholestrinase inhibited by sarin|url=http://www.rcsb.org/pdb/explore/explore.do?structureId=2JGG}}</ref> With the enzyme inhibited, acetylcholine builds up in the ] and continues to act so that any nerve impulses are, in effect, continually transmitted. Normally, the acetylcholinesterase breaks down the acetylcholine in the synaptic cleft in order to allow the effector muscle or organ to relax.
			The second process, known as the "Di-Di" process, uses equimolar quantities of ] (Difluoro) and ] (Dichloro). This reaction gives sarin, ] and others minors byproducts. The Di-Di process was used by the United States for the production of its unitary sarin stockpile.<ref name=FAS>{{cite book |chapter=Chemical Weapons Technology |chapter-url=https://irp.fas.org/threat/mctl98-2/p2sec04.pdf |via=] |title=The Militarily Critical Technologies List Part II: Weapons of Mass Destruction Technologies (ADA 330102) |publisher=] |author=Office of the Under Secretary of Defense for Acquisition and Technology |date=February 1998 |access-date=September 4, 2020}}</ref>
	==Degradation and shelf life==
	The most important chemical reactions of phosporyl halides is the ] of the bond between phosphorus and the fluoride. This P-F bond is easily broken by nucleophilic agents, such as water and ]. At high pH, sarin decomposes rapidly to nontoxic ]s derivatives.<ref>http://www.opcw.org/about-chemical-weapons/types-of-chemical-agent/nerve-agents/</ref><ref>{{Housecroft1st|page=317}}</ref>
			The scheme below shows a generic example that employs the Di-Di method as the final esterification step; in reality, the selection of reagents and reaction conditions dictate both product structure and yield. The choice of enantiomer of the mixed chloro fluoro intermediate displayed in the diagram is arbitrary, but the final substitution is selective for chloro over fluoro as the ]. Inert atmosphere and anhydrous conditions (]) are used for synthesis of sarin and other organophosphates.<ref name=FAS/>
	Sarin degrades after a period of several weeks to several months. The shelf life can be shortened by impurities in precursor materials. According to the ], some Iraqi sarin had a shelf life of only a few weeks, owing mostly to impure precursors.<ref>{{cite web|publisher=United States Central Intelligence Agency|date=July 15, 1996|url=http://www.fas.org/irp/gulf/cia/960715/72569.htm|title=Stability of Iraq's Chemical Weapon Stockpile|accessdate=2007-08-03}}</ref> The persistence of sarin can be extended through the addition of certain oils or petroleum products.
			]
			As both reactions leave considerable acid in the product, sarin produced in bulk by these methods has a short half life without further processing, and would be corrosive to containers and damaging to weapons systems. Various methods have been tried to resolve these problems. In addition to industrial ] techniques to purify the chemical itself, various additives have been tried to combat the effects of the acid, such as:
	Its otherwise short shelf life can be extended by increasing the purity of the precursor and intermediates and incorporating stabilizers such as tributylamine. In some formulations, tributylamine is replaced by ] (DIC), which allowed sarin to be stored in ] casings. In ]s, the two precursors are stored separately in the same ] and mixed to form the agent immediately before or when the shell is in flight. This approach has the dual benefit of solving the stability issue and increasing the safety of sarin munitions.
			* ] was added to US sarin produced at ].<ref name="auto">{{cite journal |title=Nerve Gas: America's Fifteen Year Struggle for Modern Chemical weapons |last=Kirby |first=Reid |date=January 2006 |journal=] |url=http://www.wood.army.mil/chmdsd/images/pdfs/Jan-June%202006/Kirby-Nerve%20Gas.pdf |access-date=December 29, 2015 |url-status=dead |archive-url=https://web.archive.org/web/20170211021417/http://www.wood.army.mil/chmdsd/images/pdfs/Jan-June%202006/Kirby-Nerve%20Gas.pdf |archive-date=February 11, 2017}}</ref>
			* ] was added to UK sarin, with relatively poor success.<ref>{{cite book |title=The Determination of Free Base in Stabilised GB |publisher=UK Ministry of Supply |year=1956 |location=United Kingdom |url=https://apps.dtic.mil/sti/tr/pdf/AD0090924.pdf |url-status=live |access-date=March 20, 2024 |archive-url=https://web.archive.org/web/20140828035415/http://www.dtic.mil/dtic/tr/fulltext/u2/090924.pdf |archive-date=August 28, 2014}}</ref> The ] cult experimented with triethylamine as well.<ref>{{cite web |title=New Information Revealed By Aum Shinrikyo Death Row Inmate Dr. Tomomasa Nakagawa |last=Tu |first=Anthony |url=http://www.foi.se/Global/V%C3%A5ra%20tj%C3%A4nster/Konferenser%20och%20seminarier/CBW%20symposium/Proceedings/Tu.pdf}}</ref>
			* ] was used by Aum Shinrikyo for acid reduction.<ref>{{cite news |title=The Sarin Gas Attack in Japan and the Related Forensic Investigation |date=June 2001 |publisher=OPCW |last=Seto |first=Yasuo |url=https://www.opcw.org/media-centre/news/2001/06/sarin-gas-attack-japan-and-related-forensic-investigation}}</ref>
			* ] was added to sarin produced at Rocky Mountain Arsenal to combat corrosion.<ref name="Chemical Agent Disposal">{{cite book |title=Chemical agent and munition disposal summary of the U.S. army's experience |publisher=United States Army |year=1987 |pages=B-30 |url=http://apps.dtic.mil/dtic/tr/fulltext/u2/a193351.pdf |url-status=live |archive-url=https://web.archive.org/web/20150719010335/http://www.dtic.mil/dtic/tr/fulltext/u2/a193351.pdf |archive-date=July 19, 2015}}</ref>
			* ] was included as part of the ] 155&nbsp;mm field artillery shell, which was a ] sarin weapon system developed by the US Army.<ref>{{cite news |last=Hedges |first=Michael |date=May 18, 2004 |title=Shell said to contain sarin poses questions for U.S. |work=] |page=A1 |url=https://www.chron.com/news/nation-world/article/artillery-shell-with-sarin-poses-dilemma-for-u-s-1974450.php |access-date=December 30, 2015 |url-status=live |archive-url=https://web.archive.org/web/20151012210347/http://www.chron.com/news/nation-world/article/Artillery-shell-with-sarin-poses-dilemma-for-U-S-1974450.php |archive-date=October 12, 2015}}</ref>
			Another byproduct of these two chemical processes is ], formed when a second isopropyl alcohol reacts with the sarin itself and from disproportionation of sarin, when distilled incorrectly. The factor of its formation in esterification is that as the concentration of DF-DCl decreases, the concentration of sarin increases, the probability of DIMP formation is greater. DIMP is a natural impurity of sarin, that is almost impossible to be eliminated, mathematically, when the reaction is a 1 mol-1 mol "one-stream".<ref>cit-OPDC. The preparatory manual to chemical warfare. Vol 1: Sarin.</ref>
	==Effects and treatment==
			:<chem>(CH3)2CHO- + CH3P(O)FOCH(CH3)2 -> CH3P(O)(OCH(CH3)2)2 + F-</chem>
	Sarin has a high volatility relative to similar nerve agents. Inhalation and absorption through the skin pose a great threat. Even vapor concentrations immediately penetrate the skin. People who absorb a non-lethal dose but do not receive immediate appropriate medical treatment may suffer permanent neurological damage.
			This chemical degrades into isopropyl methylphosphonic acid.<ref>{{cite web |work=] |title=Toxic Substances Portal – Diisopropyl Methylphosphonate (DIMP) |url=https://wwwn.cdc.gov/TSP/PHS/PHSLanding.aspx?id=967&tid=203}}</ref>
	Even at very low concentrations, sarin can be fatal. Death may follow in one minute after direct ingestion of a lethal dose if ]s, typically ] and ], are not quickly administered.<ref name=niosh /> ], an ] to ]s, is given to treat the physiological symptoms of poisoning. Since muscular response to acetylcholine is mediated through nicotinic acetylcholine receptors, atropine does not counteract the muscular symptoms. Pralidoxime can regenerate cholinesterases if administered within approximately five hours.
			==Degradation and shelf life==
	Sarin is estimated to be over 500 times more toxic than ].<ref>{{cite web|title=Council on Foreign Relations&nbsp;— Sarin|url=http://www.cfr.org/publication/9553/|accessdate=2007-08-13}}</ref> Treatment measures have been described.<ref>http://www.bt.cdc.gov/agent/sarin/basics/facts.asp</ref>
			]), 1970]]
			The most important chemical reactions of phosphoryl halides is the hydrolysis of the bond between phosphorus and the fluoride. This P-F bond is easily broken by nucleophilic agents, such as water and ]. At high ], sarin decomposes rapidly to nontoxic ] derivatives.<ref>{{cite web |title=Nerve agents |publisher=OPCW |url=http://www.opcw.org/about-chemical-weapons/types-of-chemical-agent/nerve-agents/}}</ref><ref>{{Housecroft1st|page=317}}</ref> The initial breakdown of sarin is into isopropyl methylphosphonic acid (IMPA), a chemical that is not commonly found in nature except as a breakdown product of sarin (this is useful for detecting the recent deployment of sarin as a weapon). IMPA then degrades into ] (MPA), which can also be produced by other organophosphates.<ref>Ian Sample, '']'', September 17, 2013, </ref>
	Initial symptoms following exposure to sarin are a runny nose, tightness in the chest and constriction of the ]s. Soon after, the victim has difficulty breathing and experiences nausea and drooling. As the victim continues to lose control of bodily functions, the victim vomits, defecates and urinates. This phase is followed by twitching and jerking. Ultimately, the victim becomes comatose and suffocates in a series of convulsive spasms.
			Sarin with residual acid degrades after a period of several weeks to several months. The shelf life can be shortened by impurities in ]. According to the ], some ] had a shelf life of only a few weeks, owing mostly to impure precursors.<ref>{{cite web |publisher=United States Central Intelligence Agency |date=July 15, 1996 |title=Stability of Iraq's Chemical Weapon Stockpile |url=https://fas.org/irp/gulf/cia/960715/72569.htm |access-date=August 3, 2007}}</ref>
	===Diagnostic tests===
	Controlled studies in humans have shown that a minimally toxic 0.5&nbsp;mg oral dose caused a 38% depression of both erythrocyte and plasma cholinesterase within several hours of exposure. The serum level of unbound isopropylmethylphosphonic acid (IMPA), a sarin hydrolysis product, ranged from 2-135&nbsp;µg/L in survivors of a terrorist attack during the first 4 hours post-exposure.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1407-1409.</ref>
			Along with nerve agents such as ] and ], sarin can have a short shelf life. Therefore, it is usually stored as two separate precursors that produce sarin when combined.<ref>{{cite news |title=Key Points on Sarin: The 'Most Volatile' of Nerve Agents |author=Russell Goldmanpril |date=April 6, 2017 |newspaper=New York Times |url=https://www.nytimes.com/2017/04/06/world/middleeast/sarin-nerve-agent.html}}</ref> Sarin's shelf life can be extended by increasing the purity of the precursor and intermediates and incorporating ] such as ]. In some formulations, tributylamine is replaced by ] (DIC), allowing sarin to be stored in ] casings. In ]s, the two precursors are stored separately in the same ] and mixed to form the agent immediately before or when the shell is in flight. This approach has the dual benefit of solving the stability issue and increasing the safety of sarin munitions.
	==History==		==History==
	Sarin was discovered in 1938 in ] in ] by two German scientists attempting to create stronger pesticides; it is the most toxic of the four ] made by Germany. The compound, which followed the discovery of the ] ], was named in honor of its discoverers: ], '''A'''mbros, '''R'''üdiger and Van der L'''IN'''de.		Sarin was discovered in 1938 in ]-Elberfeld in Germany by scientists at ] who were attempting to create stronger pesticides; it is the most toxic of the four ] made by Germany. The compound, which followed the discovery of the ] ], was named in honor of its discoverers: chemist ], chemist ], chemist {{interlanguage link|Gerhard Ritter (chemist)|lt=Gerhard '''R'''itter|de|Gerhard Ritter (Chemiker)|display=yes}}, and from ] Hans-Jürgen von der L'''in'''de.<ref name="Evans2008">{{cite book |author=Richard J. Evans |title=The Third Reich at War, 1939–1945 |year=2008 |publisher=Penguin |isbn=978-1-59420-206-3 |page= |url=https://archive.org/details/thirdreichatwar00evan_1 |url-access=registration |access-date=January 13, 2013}}</ref>
	===Sarin as a weapon===
	In mid-1939, the formula for the agent was passed to the ] section of the ], which ordered that it be brought into mass production for wartime use. A number of pilot plants were built, and a high-production facility was under construction (but was not finished) by the end of ]. Estimates for total sarin production by Nazi Germany range from 500&nbsp;kg to 10 tons.<ref>{{cite news
	|url= http://noblis.com/MissionAreas/nsi/BackgroundonChemicalWarfare/HistoryofChemicalWarfare/Pages/HistoryNerveGas.aspx
	|publisher=]
	|title= A Short History of the Development of Nerve Gases}}</ref> Though sarin, ] and ] were incorporated into ] shells, Germany ultimately decided not to use nerve agents against ] targets.
			===Use as a weapon===
	] warhead cutaway, showing ] Sarin bomblets (c. 1960)]]
			In mid-1939, the formula for the agent was passed to the ] section of the ], which ordered that it be brought into mass production for wartime use. Pilot plants were built, and a production facility was under construction (but was not finished) by the end of ]. Estimates for total sarin production by ] range from 500&nbsp;kg to 10&nbsp;tons.<ref>{{cite news |title=A Short History of the Development of Nerve Gases |publisher=] |url=http://noblis.com/MissionAreas/nsi/BackgroundonChemicalWarfare/HistoryofChemicalWarfare/Pages/HistoryNerveGas.aspx |url-status=dead |archive-url=https://web.archive.org/web/20110429191343/http://noblis.com/MissionAreas/nsi/BackgroundonChemicalWarfare/HistoryofChemicalWarfare/Pages/HistoryNerveGas.aspx |archive-date=April 29, 2011}}</ref>
			Though sarin, ], and ] were incorporated into ] shells, Germany did not use nerve agents against ] targets. ] refused to initiate the use of gases such as sarin as weapons.<ref>{{cite book |title=Hitler's Miracle Weapons: The Secret History Of The Rockets And Flying Crafts Of The Third Reich; from the V-1 to the A-9: Unconventional Short- and Medium-Range Weapons |last=Georg |first=Friedrich |page=49 |publisher=Helion |date=2003 |isbn=978-1-87-462262-8 |url=https://books.google.com/books?id=KAYhAQAAIAAJ}}</ref>
	* 1950s (early): ] adopted sarin as a standard chemical weapon, and both the ] and the ] produced sarin for military purposes.
	* 1953: 20-year-old ], a ] engineer from ], ], died in human testing of sarin at the ] chemical warfare testing facility in Wiltshire. Maddison had been told that he was participating in a test to "cure the common cold." Ten days after his death an ] was held in secret which returned a verdict of "misadventure". In 2004 the inquest was reopened and, after a 64-day inquest hearing, the jury ruled that Maddison had been unlawfully killed by the "application of a nerve agent in a non-therapeutic experiment."<ref>{{cite news
			] warhead cutaway, showing ] Sarin bomblets (c. 1960)]]
	|url= http://news.bbc.co.uk/1/hi/england/wiltshire/4013767.stm
	|publisher=BBC News Online
			]
	|title=Nerve gas death was 'unlawful'
	|date=November 15, 2004}}</ref>
			* 1950s (early): ] adopted sarin as a standard chemical weapon. The USSR and the United States produced sarin for military purposes.
	* 1956: Regular production of sarin ceased in the United States, though existing stocks of bulk sarin were re-distilled until 1970.
			* 1953: 20-year-old ], a ] engineer from ], ], died in human testing of sarin at the ] chemical warfare testing facility in ], England. Ten days after his death an ] was held in secret which returned a verdict of ]. In 2004, the inquest was reopened and, after a 64-day inquest hearing, the jury ruled that Maddison had been unlawfully killed by the "application of a nerve agent in a non-therapeutic experiment".<ref>{{cite news |work=BBC News Online |title=Nerve gas death was 'unlawful' |date=November 15, 2004 |url=http://news.bbc.co.uk/1/hi/england/wiltshire/4013767.stm}}</ref>
	* 1960s (developing): The US unsuccessfully sought Australian permission to test Sarin and ] on 200 "mainly Australian" troops, probably in the ] rainforest near ], ]. While this never actually took place, the planning was in advanced stages.<ref>Ansley, Greg (2008) in ''NZ Herald'', 7 July 2008.</ref>
			* 1957: Regular production of sarin chemical weapons ceased in the United States, though existing stocks of bulk sarin were re-distilled until 1970.<ref name="auto"/>
	* 1978: ] in a sworn declaration indicated that sarin was produced by the secret police of ]'s ] regime ], by ], it indicated that it was used to assassinate the state archives custodian ] and the Army Corporal ].<ref name="">{{
			* 1976: Chile's intelligence service, ], assigned biochemist ] to develop Sarin gas within its program '']'', to be used as a weapon against its opponents.<ref name="Consortium">{{cite web |last=Blixen |first=Samuel |title=Pinochet's Mad Scientist |website=] |date=January 13, 1999 |url=http://www.consortiumnews.com/1999/c011399a.html}}</ref> One of DINA's goals was to package it in spray cans for easy use, which, according to testimony by former DINA agent ], was one of the planned procedures in the 1976 ].<ref name="Consortium"/> Berríos later testified that it was used in a number of assassinations and it was planned to be used to kill inhabitants, through poisoning the water supply of ] capital ], in case ] took place.<ref name="SarinB">{{cite news |title=Towley reveló uso de gas sarín antes de ser expulsado de Chile |newspaper=] |date=September 19, 2006 |language=es}}</ref><ref>{{cite news |work=New York Times |title=Plot to kill Letelier said to involve nerve gas |date=December 13, 1981 |url=https://www.nytimes.com/1981/12/13/us/plot-to-kill-letelier-said-to-involve-nerve-gas.html |access-date=June 8, 2015}}</ref>
	cite news
			* March 1988: ]; Over two days in March, the ethnic ] city of ] in northern Iraq (population 70,000) was bombarded by ]'s ] jets with chemical bombs including sarin. An estimated 5,000 people died, almost all civilians.<ref>{{cite news |work=BBC News |title=1988: Thousands die in Halabja gas attack |date=March 16, 1988 |url=http://news.bbc.co.uk/onthisday/hi/dates/stories/march/16/newsid_4304000/4304853.stm |access-date=October 31, 2011}}</ref>
	|url=http://diario.elmercurio.com/2006/09/19/nacional/nacional/noticias/98567EED-8253-49C6-9D0D-0C91F446EE5B.htm?id={98567EED-8253-49C6-9D0D-0C91F446EE5B}
			* April 1988: Iraq used Sarin four times against Iranian soldiers at the end of the ], helping Iraqi forces to retake control of the ] during the ].
	|publisher=El Mercurio
			* 1993: The United Nations ] was signed by 162 member countries, banning the production and stockpiling of many chemical weapons, including sarin. It went into effect on April 29, 1997, and called for the complete destruction of all specified stockpiles of chemical weapons by April 2007.<ref>{{cite web |title=Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction |publisher=Organisation for the Prohibition of Chemical Weapons |url=http://www.opcw.org/html/db/cwc/eng/cwc_frameset.html |access-date=March 27, 2011}}</ref> When the convention entered force, the parties declared worldwide stockpiles of 15,047 tonnes of sarin. As of November 28, 2019, 98% of the stockpiles have been destroyed.<ref>{{cite report |author=Organisation for the Prohibition of Chemical Weapons |date=November 30, 2016 |title=Report of the OPCW on the Implementation of the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on Their Destruction in 2015 |chapter-url=https://www.opcw.org/documents-reports/annual-reports/ |chapter=Annex 3 |page=42 |access-date=March 8, 2017}}</ref>
	|title=Townley reveló uso de gas sarín antes de ser expulsado de Chile
			* 1994: ]; the Japanese religious sect ] released an impure form of sarin in ], killing eight people and harming over 500. The Australian sheep station ] was a testing ground.
	|date=September 19, 2006
			* 1995: ]; the ] sect released an impure form of sarin in the ]. Twelve people died, and over 6,200 people received injuries.<ref name="ataxia-chapter3">{{cite report |pages=91,95,100 |chapter=Chapter 3 – Rethinking the Lessons of Tokyo |chapter-url=http://www.stimson.org/books-reports/ataxia-the-chemical-and-biological-terrorism-threat-and-the-us-response/ |title=Ataxia: The Chemical and Biological Terrorism Threat and the US Response |author=Amy E. Smithson and Leslie-Anne Levy |publisher=] |date=October 2000 |id=Report No. 35 |access-date=January 6, 2017 |url-status=dead |archive-url=https://web.archive.org/web/20150924110431/http://www.stimson.org/books-reports/ataxia-the-chemical-and-biological-terrorism-threat-and-the-us-response/ |archive-date=September 24, 2015}}</ref><ref>{{cite news |last1=Martin |first1=Alex |title=1995 Aum sarin attack on Tokyo subway still haunts, leaving questions unanswered |work=The Japan Times Online |date=March 19, 2018 |url=https://www.japantimes.co.jp/news/2018/03/19/national/crime-legal/1995-aum-sarin-attack-tokyo-subway-still-haunts-leaving-questions-unanswered/}}</ref>
			* 2002: Pro-] militant ] may have been assassinated with sarin by the Russian government.<ref>{{cite news |title=More of Kremlin's Opponents Are Ending Up Dead |date=August 21, 2016 |work=The New York Times |url=https://www.nytimes.com/2016/08/21/world/europe/moscow-kremlin-silence-critics-poison.html}}</ref><ref>{{cite journal |title=The chemical weapons convention and OPCW: the challenges of the 21st century |author=Ian R Kenyon |date=June 2002 |journal=The CBW Conventions Bulletin |publisher=Harvard Sussex Program on CBW Armament and Arms Limitation |issue=56 |page=47 |url=http://www.fas.harvard.edu/~hsp/bulletin/cbwcb56.pdf}}</ref>
			* May 2004: ] detonated a 155&nbsp;mm shell containing binary precursors for sarin near a U.S. convoy in ]. The shell was designed to mix the chemicals as it spun during flight. The detonated shell released only a small amount of sarin gas, either because the explosion failed to mix the binary agents properly or because the chemicals inside the shell had degraded with age. Two United States soldiers were treated after displaying the early symptoms of exposure to sarin.<ref>{{cite news |title=Bomb said to hold deadly Sarin gas explodes in Iraq |last=Brunker |first=Mike |date=May 17, 2004 |publisher=MSNBC |url=https://www.nbcnews.com/id/wbna4997808 |access-date=August 3, 2007}}</ref>
			* March 2013: ]; Sarin was used in an attack on a town west of ] city in ], killing 28 and wounding 124.<ref name="Khan al-Assal">{{cite news |last=Barnard |first=Anne |title=Syria and Activists Trade Charges on Chemical Weapons |newspaper=The New York Times |date=March 19, 2013 |url=https://www.nytimes.com/2013/03/20/world/middleeast/syria-developments.html?pagewanted=all |access-date=March 19, 2013}}</ref>
			* August 2013: ]; Sarin was used in multiple simultaneous attacks in the ] region of the ] Governorate of Syria during the ].<ref name="PortonDown_sarin_Ghouta">{{cite news |last=Murphy |first=Joe |title=Cameron: British scientists have proof deadly Sarin gas was used in chemical weapons attack |date=September 5, 2013 |newspaper=The Daily Telegraph |df=mdy-all |url=https://www.independent.co.uk/news/world/middle-east/cameron-british-scientists-have-proof-deadly-sarin-gas-was-used-in-chemical-weapons-attack-8800528.html |url-status=live |archive-url=https://web.archive.org/web/20130906013530/http://www.independent.co.uk/news/world/middle-east/cameron-british-scientists-have-proof-deadly-sarin-gas-was-used-in-chemical-weapons-attack-8800528.html |archive-date=September 6, 2013}}</ref> Varying<ref name="MSF_neurotoxic">{{cite news |title=Syria: Thousands suffering neurotoxic symptoms treated in hospitals supported by MSF |publisher=] |date=August 24, 2013 |df=mdy-all |url=http://www.msf.org/article/syria-thousands-suffering-neurotoxic-symptoms-treated-hospitals-supported-msf |access-date=August 24, 2013 |url-status=live |archive-url=https://web.archive.org/web/20130826214418/http://www.msf.org/article/syria-thousands-suffering-neurotoxic-symptoms-treated-hospitals-supported-msf |archive-date=August 26, 2013}}</ref> sources gave a death toll of 322<ref name="NGO">{{cite news |title=NGO says 322 died in Syria 'toxic gas' attacks |agency=AFP |date=August 25, 2013 |url=http://www.ndtv.com/article/world/322-died-in-syria-toxic-gas-attacks-ngo-410028 |access-date=August 24, 2013}}</ref> to 1,729.<ref name="opposition">{{cite news |title=Bodies still being found after alleged Syria chemical attack: opposition |publisher=Dailystar.com.lb |url=http://www.dailystar.com.lb/News/Middle-East/2013/Aug-22/228268-bodies-still-being-found-after-alleged-syria-chemical-attack-opposition.ashx |access-date=August 24, 2013 |url-status=dead |archive-url=https://web.archive.org/web/20190305230820/http://www.dailystar.com.lb/News/Middle-East/2013/Aug-22/228268-bodies-still-being-found-after-alleged-syria-chemical-attack-opposition.ashx |archive-date=March 5, 2019}}</ref>
			* April 2017: ]: The ] released sarin gas in rebel-held Idlib Province in Syria during an ].<ref>{{cite news |title=Chemical attack of 4 April 2017 (Khan Sheikhoun): Clandestine Syrian chemical weapons programme |language=en |url=http://www.diplomatie.gouv.fr/IMG/pdf/170425_-_evaluation_nationale_-_anglais_-_final_cle0dbf47-1.pdf |access-date=April 26, 2017}}</ref><ref>{{cite news |title=Syrian regime dropped sarin on rebel-held town in April, UN confirms |last=Chulov |first=Martin |date=September 6, 2017 |work=The Guardian |language=en-GB |issn=0261-3077 |url=https://www.theguardian.com/world/2017/sep/06/syrian-regime-dropped-sarin-on-rebel-held-town-in-april-un-confirms |access-date=December 29, 2017}}</ref>
			* April 2018: Victims of the ] in Syria reported to have symptoms consistent with exposure to sarin and other agents. On July 6, 2018, the Fact-Finding Mission (FFM) of the OPCW published their interim report. The report stated that, "The results show that no organophosphorous nerve agents or their degradation products were detected in the environmental samples or in the plasma samples taken from alleged casualties". The chemical agent used in the attack was later identified as elemental ].<ref>{{cite report |title=OPCW Issues Fact-Finding Mission Reports on Chemical Weapons Use Allegations in Douma, Syria in 2018 and in Al-Hamadaniya and Karm Al-Tarrab in 2016 |publisher=Organisation for the Prohibition of Chemical Weapons |date=July 6, 2018 |url=https://www.opcw.org/news/article/opcw-issues-fact-finding-mission-reports-on-chemical-weapons-use-allegations-in-douma-syria-in-2018-and-in-al-hamadaniya-and-karm-al-tarrab-in-2016/ |access-date=July 14, 2018
	}}</ref>		}}</ref>
			* July 2023: The U.S. destroyed the last of its declared chemical weapons, a sarin nerve agent-filled ], on July 7, 2023.<ref>{{cite web |title=U.S. destroys last of its declared chemical weapons |website=CBS |date=July 7, 2023 |url=https://www.cbsnews.com/news/us-destroys-last-chemical-weapons/ |access-date=July 11, 2023}}</ref>
	* 1980–1988: ] used sarin against ] during the ]. During the 1990–91 ], Iraq still had large stockpiles available which were found as coalition forces advanced north.{{Citation needed|date=November 2007}}
	* 1988: Over the span of two days in March, the ethnic ] city of ] in northern Iraq (population 70,000) was bombarded with chemical and cluster bombs, which included sarin, in the ]. An estimated 5,000 people died.
			==See also==
	* 1991: ] established the term "weapon of mass destruction" and called for the immediate destruction of chemical weapons in Iraq, and eventual destruction of all chemical weapons globally.<ref>], full text at wikisource.org</ref>
			* ]
	* 1993: The United Nations ] was signed by 162 member countries, banning the production and stockpiling of many chemical weapons, including sarin. It went into effect on 29 April 1997, and called for the complete destruction of all specified stockpiles of chemical weapons by April 2007.<ref></ref>
			* ]
	* 1994: The Japanese religious sect ] released an impure form of sarin in ]. (see ])
			* ]
	* 1995: ] sect released an impure form of sarin in the ]. Thirteen people died. (see ])
			* ]
	* 1998: In the US, '']'' and ] ran news stories alleging that in 1970 ] ] engaged in a covert operation called ], in which they deliberately dropped sarin-containing weapons on U.S. troops who had defected in ]. CNN and ''Time Magazine'' later retracted the stories and fired the producers responsible.<ref>{{cite news|url=http://www.cnn.com/US/9807/21/pentagon.tailwind.02/|publisher=CNN|title=Cohen: No nerve gas used in Operation Tailwind|date=July 21, 1998|accessdate=2007-08-03 |archiveurl = http://web.archive.org/web/20070228163658/http://www.cnn.com/US/9807/21/pentagon.tailwind.02/ <!-- Bot retrieved archive --> |archivedate = 2007-02-28}}</ref>
	* 2004: On May 14 ] fighters in ] detonated a 155&nbsp;mm shell containing several litres of binary precursors for sarin. The shell was designed to mix the chemicals as it spins during flight. The detonated shell released only a small amount of sarin gas, either because the explosion failed to mix the binary agents properly or because the chemicals inside the shell had degraded significantly with age. Two United States soldiers were treated after displaying the early symptoms of exposure to sarin.<ref>{{cite news|url=http://www.msnbc.msn.com/id/4997808/|title=Bomb said to hold deadly sarin gas explodes in Iraq|date=May 17, 2004|accessdate=2007-08-03|publisher=MSNBC}}</ref>
	==References==		==References==
	{{Reflist|2}}		{{Reflist|30em}}
	==External links==		==External links==
	*		*
			*
	*
			*
	*
			*
	{{Chemical warfare}}		{{Chemical agents}}
	{{U.S. chemical weapons}}		{{U.S. chemical weapons}}
			{{Acetylcholine metabolism and transport modulators}}
	{{Cholinergics}}
			{{Oxygen compounds}}
			{{Fluorine compounds}}
			{{Phosphorus compounds}}
	]		]
	]		]
	]		]
			]
			]
			]
			]
			]
			]
			]
	]		]
	]		]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]