Cadaverine Explained

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. 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

Cadaverine is produced by decarboxylation of lysine.^[1] It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.

History

Putrescine^[2] and cadaverine^[3] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).^[4]

Receptors

In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.^[5] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.^[6]

Clinical significance

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.^[7]

Derivatives

• Pentolinium and pentamethonium.

Toxicity

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).^[8]

See also

• Putrescine
• Skatole

External links

• • GMD MS Spectrum

Notes and References

1. Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65,
2. Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
3. 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.)
4. Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
5. Li, Q. Tachie-Baffour, Y. Liu, Z. Baldwin, MW. Kruse, AC. Liberles, SD. Non-classical amine recognition evolved in a large clade of olfactory receptors.. eLife. 2015. 4. e10441. 10.7554/eLife.10441. 26519734. 4695389 . free .
6. Izquierdo, C. Gomez-Tamayo, JC. Nebel, J-C. Pardo, L. Gonzalez, A. Identifying human diamine sensors for death related putrescine and cadaverine molecules.. PLOS Computational Biology. 2018. 14. 1. e1005945. 10.1371/journal.pcbi.1005945. 29324768. 5783396. 2018PLSCB..14E5945I . free .
7. Yeoman, CJ. Thomas, SM. Miller, ME. Ulanov, AV. Torralba, M. Lucas, S. Gillis, M. Cregger, M. Gomez, A. Ho, M. Leigh, SR. Stumpf, R. Creedon, DJ. Smith, MA. Weisbaum, JS. Nelson, KE. Wilson, BA. White, BA. A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.. PLOS ONE. 2013. 8. 2. e56111. 10.1371/journal.pone.0056111. 23405259. 3566083. 2013PLoSO...856111Y. free.
8. Til. H.P.. Falke. H.E.. Prinsen. M.K.. Willems. M.I.. Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats. Food and Chemical Toxicology . 35. 3–4. 1997. 337–348. 0278-6915. 10.1016/S0278-6915(97)00121-X. 9207896.