Editing Cadaverine

{{Short description|Foul-smelling diamine compound}}
{{Chembox
| Watchedfields  = changed
| verifiedrevid  = 443671098
| ImageFile1     = Pentane-1,5-diamine 200.svg
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageSize1     = 200
| ImageName1     = Skeletal formula of cadaverine
| ImageCaption1  = [[Skeletal formula]]
| ImageFile2     = Cadaverine-3D-balls.png
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageSize2     = 160
| ImageName2     = Ball and stick model of cadaverine
| ImageCaption2  = [[Ball-and-stick model]]<ref>{{Cite journal|url=https://dx.doi.org/10.5517/cc4g861|title = CSD Entry: QATWEN : 1,5-Pentanediamine|website=[[Cambridge Structural Database]]: Access Structures| year=2001 |publisher=[[Cambridge Crystallographic Data Centre]]|doi=10.5517/cc4g861|access-date = 2021-11-07| last1=Thalladi | first1=V.R. | last2=Boese | first2=R. | last3=Weiss | first3=H.-C. }}</ref>
| PIN            = Pentane-1,5-diamine
| OtherNames     = 1,5-Diaminopentane, pentamethylenediamine
| Section1       = {{Chembox Identifiers
|CASNo = 462-94-2
|CASNo_Ref = {{cascite|correct|CAS}}
|PubChem = 273
|ChemSpiderID = 13866593
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|UNII = L90BEN6OLL
|UNII_Ref = {{fdacite|correct|FDA}}
|EINECS = 207-329-0
|UNNumber = 2735
|DrugBank = DB03854
|DrugBank_Ref = {{drugbankcite|correct|drugbank}}
|KEGG = C01672
|KEGG_Ref = {{keggcite|correct|kegg}}
|MeSHName = Cadaverine
|ChEBI = 18127
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 119296
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = SA0200000
|Beilstein = 1697256
|Gmelin = 2310
|3DMet = B00334
|SMILES = NCCCCCN
|StdInChI = 1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = VHRGRCVQAFMJIZ-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
|C = 5 |H = 14 |N = 2 
|Appearance = Colourless liquid
|Odor = very unpleasant; putrid 
|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=[[Angewandte Chemie International Edition|Angew. Chem. Int. Ed.]]|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|[[n-Butylamine|''n''-Butylamine]]|[[Putrescine]]|[[Pentylamine]]|[[Hexamethylenediamine]]}}
}}
}}
'''Cadaverine''' is an [[organic compound]] with the formula (CH<sub>2</sub>)<sub>5</sub>(NH<sub>2</sub>)<sub>2</sub>. Classified as a [[diamine]], 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 [[putrefaction]] of [[Tissue (biology)#Animal tissue|animal tissue]]. Together with [[putrescine]], it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

==Production==
Cadaverine is produced by [[decarboxylation]] of [[lysine]].<ref name=Legrum>Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S.&nbsp;65, {{ISBN|978-3-8348-1245-2}}</ref> It can be synthesized by many methods including the hydrogenation of [[glutaronitrile]] and the reactions of 1,5-dichloropentane.<ref name=Ull/>

==History==
[[Putrescine]]<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany:  August Hirschwald, 1885), [https://books.google.com/books?id=gqt9piJJ_TkC&dq=putrescin&pg=PA43 page 43].</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany:  August Hirschwald, 1885), [https://books.google.com/books?id=gqt9piJJ_TkC&dq=cadaverin&pg=PA39 page 39].  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 [[Berlin]] physician [[Ludwig Brieger]] (1849–1919).<ref>Brief biography of [http://www.sammlungen.hu-berlin.de/dokumente/14948/ Ludwig Brieger] {{Webarchive|url=https://web.archive.org/web/20111003041704/http://www.sammlungen.hu-berlin.de/dokumente/14948/ |date=2011-10-03 }} (in German).  Biography of [http://jewishencyclopedia.com/articles/3708-brieger-ludwig Ludwig Brieger] in English.</ref> It was named from the English adjective ''cadaverous''.

==Receptors==
In [[zebrafish]], the [[trace amine-associated receptor]] 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 [[TAAR6]] and [[TAAR8]].<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==
[[Semen|Seminal plasma]] 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 [[bacterial vaginosis]] has been linked to cadaverine and [[putrescine]].<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>

==Derivatives==
*[[Pentolinium]] and [[pentamethonium]].

==Toxicity==
[[Acute toxicity|Acute oral toxicity]] of cadaverine is 2,000&nbsp;mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180&nbsp;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==
* [[Putrescine]]
* [[Skatole]]

== References ==

{{reflist | 30em}}

==External links==
*{{Commonscatinline|Pentamethylenediamine}}
*[http://gmd.mpimp-golm.mpg.de/Spectrums/BAE756CA-A27B-4388-ABB7-5FD32C380232.aspx GMD MS Spectrum]

{{Amino acid metabolism intermediates}}
{{Authority control}}

[[Category:Diamines]]
[[Category:Foul-smelling chemicals]]
[[Category:Substances discovered in the 19th century]]