Cadaverine
Template:Short description Template:Chembox Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor.<ref name=Ull>Template:Ullmann</ref> It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.
ProductionEdit
Cadaverine is produced by decarboxylation of lysine.<ref name=Legrum>Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, Template:ISBN</ref> It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.<ref name=Ull/>
HistoryEdit
Putrescine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.</ref> and cadaverine<ref>Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39. From page 39: Ich nenne das neue Diamin C5H16N2: "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, C5H16N2, "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 Ludwig Brieger Template:Webarchive (in German). Biography of Ludwig Brieger in English.</ref> It was named from the English adjective cadaverous.
ReceptorsEdit
In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.<ref>Template:Cite journal</ref> In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.<ref>Template:Cite journal</ref>
Clinical significanceEdit
Seminal plasma contains cadaverine as basic amines.<ref>Template:Cite journal</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>Template:Cite journal</ref>
DerivativesEdit
ToxicityEdit
Acute oral toxicity 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>Template:Cite journal</ref>
See alsoEdit
ReferencesEdit
External linksEdit
Template:Amino acid metabolism intermediates Template:Authority control