Cadaverine is anorganic compound with the formula (CH2)5(NH2)2. Classified as adiamine, it is a colorless liquid with an unpleasant odor.[3] It is present in small quantities in living organisms but is often associated with theputrefaction ofanimal tissue. Together withputrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.
Cadaverine is produced bydecarboxylation oflysine.[4] It can be synthesized by many methods including the hydrogenation ofglutaronitrile and the reactions of 1,5-dichloropentane.[3]
Putrescine[5] and cadaverine[6] were first described in 1885 by theBerlin physicianLudwig Brieger (1849–1919).[7] It was named from the English adjectivecadaverous.
Inzebrafish, thetrace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.[8] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the humanTAAR6 andTAAR8.[9]
Seminal plasma contains cadaverine as basic amines.[10] Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. The odor commonly associated withbacterial vaginosis has been linked to cadaverine andputrescine.[11]
^Wolfgang Legrum:Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65,ISBN978-3-8348-1245-2
^Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885),page 43.
^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.)
^Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats".Food and Chemical Toxicology.35 (3–4):337–348.doi:10.1016/S0278-6915(97)00121-X.ISSN0278-6915.PMID9207896.
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