MOLECULE

Cadaverine

Cadaverine, also known as 1,5-diaminopentane, belongs to the class of organic compounds known as monoalkylamines. These are organic compounds containing a primary aliphatic amine group. Cadaverine is a strong basic compound (based on its pKa). Cadaverine is a foul-smelling diamine formed by bacterial decarboxylation of lysine that occurs during protein hydrolysis during putrefaction of animal and/or plant tissue. However, cadaverine is not purely associated with putrefaction. It is also produced in small quantities by mammals. In particular, it is partially responsible for the distinctive smell of urine and semen. Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism. Cadaverine has been shown to bind to mammalian trace amine associated receptors TAAR6 and TAAR8 ( PMID: 29324768) and to act as a “necromone” triggering avoidance or attractive responses, which are fundamental for the survival of a wide range of species. Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of more than 2000 mg/kg body weight ( PMID: 9207896). Cadaverine can be naturally found in some bacterial species including Corynebacterium (PMID: 27872963). In addition many plants have been found to synthesize it. For instance, plants from the Leguminosae family have been shown to produce cadaverine and use it as a precursor in the biosynthesis of quinolizidine alkaloids. Quinolizidine alkaloids are secondary metabolites that are involved in insect defense and also display therapeutic pharmacological properties.