| Revision as of 12:35, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit |
Latest revision as of 19:17, 20 December 2024 edit undoHeadbomb (talk | contribs)Edit filter managers, Autopatrolled, Extended confirmed users, Page movers, File movers, New page reviewers, Pending changes reviewers, Rollbackers, Template editors454,421 edits ce |
| (112 intermediate revisions by 83 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Foul-smelling diamine compound}} |
|
{{chembox |
|
|
|
{{Chembox |
|
| verifiedrevid = 443493210 |
|
|
|
|Watchedfields = changed |
|
|ImageFile=Cadaverine-2D-skeletal.png |
|
|
|
|verifiedrevid = 443671098 |
|
|ImageSize= |
|
|
|
|ImageFile1 = Pentane-1,5-diamine 200.svg |
|
|ImageFile2=Cadaverine-3D-balls.png |
|
|
|
|ImageFile1_Ref = {{chemboximage|correct|??}} |
|
|IUPACName=pentane-1,5-diamine |
|
|
|
|ImageSize1 = 200 |
|
|OtherNames= |
|
|
|
|ImageName1 = Skeletal formula of cadaverine |
|
|Section1= {{Chembox Identifiers |
|
|
|
|ImageCaption1 = ] |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
|
|
|ImageFile2 = Cadaverine-3D-balls.png |
|
| KEGG = C01672 |
|
|
|
|ImageFile2_Ref = {{chemboximage|correct|??}} |
|
| InChI = 1/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 |
|
|
|
|ImageSize2 = 160 |
|
| InChIKey = VHRGRCVQAFMJIZ-UHFFFAOYAX |
|
|
|
|ImageName2 = Ball and stick model of cadaverine |
|
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
|
|ImageCaption2 = ]<ref>{{Cite journal|url=https://dx.doi.org/10.5517/cc4g861|title = CSD Entry: QATWEN : 1,5-Pentanediamine|website=]: Access Structures| year=2001 |publisher=]|doi=10.5517/cc4g861|access-date = 2021-11-07| last1=Thalladi | first1=V.R. | last2=Boese | first2=R. | last3=Weiss | first3=H.-C. }}</ref> |
|
| ChEMBL = 119296 |
|
|
|
|PIN = Pentane-1,5-diamine |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|OtherNames = 1,5-Diaminopentane, pentamethylenediamine |
|
| StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 |
|
|
|
|Section1 = {{Chembox Identifiers |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|CASNo = 462-94-2 |
|
| StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
|
|PubChem = 273 |
|
| CASNo=462-94-2 |
|
|
|
|ChemSpiderID = 13866593 |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 13866593 |
|
|
|
|UNII = L90BEN6OLL |
|
| PubChem=273 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|EINECS = 207-329-0 |
|
| UNII = L90BEN6OLL |
|
|
|
|UNNumber = 2735 |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
|
| ChEBI = 18127 |
|
|DrugBank = DB03854 |
|
|
|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = DB03854 |
|
|
|
|KEGG = C01672 |
|
| SMILES=NCCCCCN |
|
|
|
|KEGG_Ref = {{keggcite|correct|kegg}} |
|
| MeSHName=Cadaverine |
|
|
|
|MeSHName = Cadaverine |
|
}} |
|
|
|
|ChEBI = 18127 |
|
|Section2= {{Chembox Properties |
|
|
|
|ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| Formula=C<sub>5</sub>H<sub>14</sub>N<sub>2</sub> |
|
|
|
|ChEMBL = 119296 |
|
| MolarMass=102.178 |
|
|
|
|ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
| Appearance= |
|
|
|
|RTECS = SA0200000 |
|
| Density=0.870 g/cm³ |
|
|
|
|Beilstein = 1697256 |
|
| MeltingPt=9 °C |
|
|
|
|Gmelin = 2310 |
|
| BoilingPt=178-180 °C |
|
|
|
|3DMet = B00334 |
|
| Solubility= |
|
|
|
|SMILES = NCCCCCN |
|
}} |
|
|
|
|StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 |
|
|Section3= {{Chembox Hazards |
|
|
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| MainHazards= |
|
|
|
|StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N |
|
| FlashPt= |
|
|
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| Autoignition= |
|
|
}} |
|
|
}} |
|
}} |
|
|
|Section2 = {{Chembox Properties |
|
'''Cadaverine''' is a foul-smelling compound produced by ] ] during ] of animal tissue. Cadaverine is a toxic<ref>Lewis 1998, Page 212</ref> ] with the formula NH<sub>2</sub>(CH<sub>2</sub>)<sub>5</sub>NH<sub>2</sub>, which is similar to ]. Cadaverine is also known by the names '''1,5-pentanediamine''' and '''pentamethylenediamine'''. |
|
|
|
|C = 5 |H = 14 |N = 2 |
|
|
|
|
|
|Appearance = Colourless liquid |
|
==History== |
|
|
|
|Odor = Unpleasant |
|
]<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), .</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), . From page 39: Ich nenne das neue Diamin C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)</ref> were first described in 1885 by the ] physician ] (1849–1919).<ref>Brief biography of (in German).</ref> |
|
|
|
|Density = 873,0 g/l |
|
|
|MeltingPtC = 11.83<ref>{{cite journal|title=The Melting Point Alternation in ''α'',''ω''-Alkanediols and ''α'',''ω''-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions|first1=V. R.|last1=Thalladi|first2=R.|last2=Boese|first3=H. C.|last3=Weiss|journal=]|year=2000|volume=39|issue=5|pages=918–922|doi=10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E|pmid=10760893 }}</ref> |
|
|
|BoilingPtK = 452.2 |
|
|
|Solubility = Soluble |
|
|
|SolubleOther = conventional organic solvents |
|
|
|Solvent = other solvents |
|
|
|LogP = −0.123 |
|
|
|RefractIndex = 1.458 |
|
|
|pKa = 10.25, 9.13 |
|
|
}} |
|
|
|Section3 = {{Chembox Hazards |
|
|
|GHSPictograms = {{GHS corrosion}} |
|
|
|GHSSignalWord = '''DANGER''' |
|
|
|HPhrases = {{H-phrases|314}} |
|
|
|PPhrases = {{P-phrases|280|305+351+338|310}} |
|
|
|NFPA-H = 3 |NFPA-F = 2 |NFPA-R = 0 |
|
|
|FlashPtC = 62 |
|
|
|LD50 = 2000 mg/kg (oral, rat) |
|
|
}} |
|
|
|Section4 = {{Chembox Related |
|
|
|OtherFunction_label = alkanamines |
|
|
|OtherFunction = {{Unbulleted list|]|]|]|]}} |
|
|
}} |
|
|
}} |
|
|
'''Cadaverine''' is an ] with the formula (CH<sub>2</sub>)<sub>5</sub>(NH<sub>2</sub>)<sub>2</sub>. Classified as a ], it is a colorless liquid with an unpleasant odor.<ref name=Ull>{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1=Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}</ref> It is present in small quantities in living organisms but is often associated with the ] of ]. Together with ], it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors. |
|
|
|
|
|
==Production== |
|
==Production== |
|
|
Cadaverine is produced by ] of ].<ref name=Legrum>Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, {{ISBN|978-3-8348-1245-2}}</ref> It can be synthesized by many methods including the hydrogenation of ] and the reactions of 1,5-dichloropentane.<ref name=Ull/> |
|
Cadaverine is the ] product of the ] ]. |
|
|
|
|
|
|
|
==History== |
|
However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive odors of ] and ]. |
|
|
|
]<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), .</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" (Berlin, Germany: August Hirschwald, 1885), . From page 39: Ich nenne das neue Diamin C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C<sub>5</sub>H<sub>16</sub>N<sub>2</sub>, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)</ref> were first described in 1885 by the ] physician ] (1849–1919).<ref>Brief biography of {{Webarchive|url=https://web.archive.org/web/20111003041704/http://www.sammlungen.hu-berlin.de/dokumente/14948/ |date=2011-10-03 }} (in German). Biography of in English.</ref> It was named from the English adjective ''cadaverous''. |
|
|
|
|
|
==Receptors== |
|
|
In ], the ] 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.<ref>{{cite journal|author=Li, Q|author2=Tachie-Baffour, Y|author3=Liu, Z|author4=Baldwin, MW|author5=Kruse, AC|author6=Liberles, SD|title=Non-classical amine recognition evolved in a large clade of olfactory receptors.|journal=eLife|year=2015|volume=4|pages=e10441|doi=10.7554/eLife.10441|pmid=26519734|pmc=4695389 |doi-access=free }}</ref> In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human ] and ].<ref>{{cite journal|author=Izquierdo, C|author2=Gomez-Tamayo, JC|author3=Nebel, J-C|author4=Pardo, L|author5=Gonzalez, A|title=Identifying human diamine sensors for death related putrescine and cadaverine molecules.|journal=PLOS Computational Biology|year=2018|volume=14|issue=1|pages=e1005945|doi=10.1371/journal.pcbi.1005945|pmid=29324768|pmc=5783396|bibcode=2018PLSCB..14E5945I |doi-access=free }}</ref> |
|
|
|
|
|
==Clinical significance== |
|
==Clinical significance== |
|
|
] contains cadaverine as basic amines.<ref>{{cite journal|author= Jana Vitku|author2= Lucie Kolatorova|author3=Richard Hampl|title=Occurrence and reproductive roles of hormones in seminal plasma.|journal= Basic Clin Androl |year=2017|volume=27|issue=19|page= 19|doi=10.1186/s12610-017-0062-y|pmid=29046808|pmc=5640966|bibcode=|doi-access=free}}</ref> Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated with ] has been linked to cadaverine and ].<ref>{{cite journal|author=Yeoman, CJ|author2=Thomas, SM|author3=Miller, ME|author4=Ulanov, AV|author5=Torralba, M|author6=Lucas, S|author7=Gillis, M|author8=Cregger, M|author9=Gomez, A|author10=Ho, M|author11=Leigh, SR|author12=Stumpf, R|author13=Creedon, DJ|author14=Smith, MA|author15=Weisbaum, JS|author16=Nelson, KE|author17=Wilson, BA|author18=White, BA|title=A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.|journal=PLOS ONE|year=2013|volume=8|issue=2|pages=e56111|doi=10.1371/journal.pone.0056111|pmid=23405259|pmc=3566083|bibcode=2013PLoSO...856111Y|doi-access=free}}</ref> |
|
Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. |
|
|
|
|
|
|
==Derivatives== |
|
|
*] and ]. |
|
|
|
|
|
==Toxicity== |
|
==Toxicity== |
|
Cadaverine is toxic in large doses. In rats it had an ] of more than 2000 mg/kg body weight.<ref> |
|
] of cadaverine is 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).<ref>{{cite journal |last1=Til|first1=H.P.|last2=Falke|first2=H.E.|last3=Prinsen|first3=M.K.|last4=Willems|first4=M.I.|title=Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats|journal=Food and Chemical Toxicology |volume=35|issue=3–4|year=1997|pages=337–348|issn=0278-6915|doi=10.1016/S0278-6915(97)00121-X|pmid=9207896}}</ref> |
|
|
|
|
|
== See also == |
|
==See also== |
|
* ] |
|
* ] |
|
|
* ] |
|
|
|
|
|
==Notes== |
|
== References == |
|
{{reflist}} |
|
|
|
|
|
|
|
{{reflist | 30em}} |
|
==References== |
|
|
*{{cite book |
|
|
| last =Lewis |
|
|
| first =Robert Alan |
|
|
| title =Lewis' Dictionary of Toxicology |
|
|
| publisher =CRC Press |
|
|
| year =1998 |
|
|
| isbn =1566702232 }} |
|
|
|
|
|
|
|
==External links== |
|
] |
|
|
|
*{{Commonscatinline|Pentamethylenediamine}} |
|
] |
|
|
|
* |
|
|
|
|
|
|
{{Amino acid metabolism intermediates}} |
|
] |
|
|
|
{{Authority control}} |
|
] |
|
|
|
|
|
] |
|
|
] |
|
] |
|
|
] |
|
] |
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|