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. It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.

History

Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919). 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. In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.

Clinical significance

Seminal plasma contains cadaverine as basic amines. 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.

Derivatives

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).