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. The ...

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

diamine A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to primary diamines, as those are the most reactive. In terms of quantities p ...

, 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 Putrefaction is the fifth stage of death, following pallor mortis, algor mortis, rigor mortis, and livor mortis. This process references the breaking down of a body of an animal, such as a human, post-mortem. In broad terms, it can be viewed ...

of animal tissue.

Production

Cadaverine is produced by

decarboxylation Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ...

lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. It contains an α-amino group (which is in the protonated form under biological conditions), an α-carboxylic acid group (which is in the deprotonated −C ...

.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 Glutaronitrile, also pentanedinitrile, is a nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The prefix '' cyano-'' is used interchangeably with the term ''nitrile'' in industrial literature. Nitri ...

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, b ...

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 constitue ...

physician

Ludwig Brieger Ludwig may refer to: People and fictional characters * Ludwig (given name), including a list of people and fictional characters * Ludwig (surname), including a list of people * Ludwig Ahgren, or simply Ludwig, American YouTube live streamer and co ...

(1849–1919).

Receptors

zebrafish The zebrafish (''Danio rerio'') is a freshwater fish belonging to the minnow family ( Cyprinidae) of the order Cypriniformes. Native to South Asia, it is a popular aquarium fish, frequently sold under the trade name zebra danio (and thus often ...

, the

trace amine-associated receptor Trace amine-associated receptors (TAARs), sometimes referred to as trace amine receptors (TAs or TARs), are a class of G protein-coupled receptors that were discovered in 2001. TAAR1, the first of six functional human TAARs, has gained considerab ...

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 c ...

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 urination ...

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, b ...

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).

References

External links

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