Cadaverine is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula (CH₂)₅(NH₂)₂. Classified as 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.

Production

Cadaverine is produced by decarboxylation of lysine.Wolfgang Legrum: ''Riechstoffe, zwischen Gestank und Duft'', Vieweg + Teubner Verlag (2011) S. 65, It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.

History

Putrescine Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh ...

and cadaverine were first described in 1885 by the

Berlin Berlin ( , ) is the capital and largest city of Germany by both area and population. Its 3.7 million inhabitants make it the European Union's most populous city, according to population within city limits. One of Germany's sixteen constitu ...

physician Ludwig Brieger (1849–1919).

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 Trace amine associated receptor 6, also known as TAAR6, is a protein which in humans is encoded by the ''TAAR6'' gene. Function TAAR6 belongs to the trace amine-associated receptor family. Trace amines are endogenous amine compounds that are ...

and

TAAR8 Trace amine-associated receptor 8 is a protein that in humans is encoded by the ''TAAR8'' gene. In humans, TAAR8 is the only trace amine-associated receptor that is known to be Gi/o-coupled. In humans, molecular modelling and docking experiments ...

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 Bacterial vaginosis (BV) is a disease of the vagina caused by excessive growth of bacteria. Common symptoms include increased vaginal discharge that often smells like fish. The discharge is usually white or gray in color. Burning with urinati ...

has been linked to cadaverine and

putrescine Putrescine is an organic compound with the formula (CH2)4(NH2)2. It is a colorless solid that melts near room temperature. It is classified as a diamine. Together with cadaverine, it is largely responsible for the foul odor of putrefying flesh ...

Derivatives

Pentolinium Pentolinium is a ganglionic blocking agent which acts as a nicotinic acetylcholine receptor antagonist. Formulated as the pentolinium tartrate salt, it is also known as Ansolysen. It can be used as an antihypertensive drug during surgery or to c ...

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).

References

External links

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GMD MS Spectrum
{{Authority control Diamines Foul-smelling chemicals