Cadaverine
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.[1] 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.
Production
[edit]Cadaverine is produced by decarboxylation of lysine.[2] It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.[1]
History
[edit]Putrescine[3] and cadaverine[4] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[5] It was named from the English adjective cadaverous.
Receptors
[edit]In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.[6] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.[7]
Clinical significance
[edit]Seminal plasma contains cadaverine as basic amines.[8] 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.[9]
Derivatives
[edit]Toxicity
[edit]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).[10]
See also
[edit]References
[edit]- ↑ 1.0 1.1 Template:Ullmann
- ↑ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2
- ↑ 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.)
- ↑ Brief biography of Ludwig Brieger Archived 2011-10-03 at the Wayback Machine (in German). Biography of Ludwig Brieger in English.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ Jana Vitku; Lucie Kolatorova; Richard Hampl (2017). "Occurrence and reproductive roles of hormones in seminal plasma". Basic Clin Androl. 27 (19): 19. doi:10.1186/s12610-017-0062-y. PMC 5640966. PMID 29046808.
- ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
- ↑ 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. ISSN 0278-6915. PMID 9207896.
External links
[edit]
Media related to Pentamethylenediamine at Wikimedia Commons- GMD MS Spectrum
