Putrescine

Putrescine (sometimes spelled putrescin or putrescene) is an organic chemical compound NH2(CH2)4NH2 (1,4-diaminobutane or butanediamine).

It is related to cadaverine; both are produced by the breakdown of amino acids in living and dead organisms. The two compounds are largely responsible for the foul odor of putrefying flesh, but also contribute to the odor of such processes as bad breath and bacterial vaginosis. They are also found in semen and some microalgae, together with related molecules like spermine and spermidine.

Production and use
Putrescine is produced on industrial scale by hydrogenation of succinonitrile, which is produced by addition of hydrogen cyanide to acrylonitrile. Putrescine is reacted with adipic acid to yield the polyamide Nylon-4,6, which is marketed by DSM under the trade name Stanyl®.

Biochemistry
Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn attacks another s-adenosyl methionine and converts it to spermine.

Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.

History
Putrescine and cadaverine were first described by the Berlin physician Ludwig Brieger in 1885.

Cultural references
Putrescine is featured as a non-lethal weapon in the science fiction novel Zodiac, by Neal Stephenson. Its use is also suggested as a practical joke in an episode of Dinosaur Comics.