Cadaverine is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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

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

, 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, livor mortis, algor mortis, and rigor mortis. This process references the breaking down of a body of an animal Post-mortem interval, post-mortem. In broad terms, it can be view ...

of animal tissue. Together with

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 Putrefaction, putref ...

, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

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 ...

lysine Lysine (symbol Lys or K) is an α-amino acid that is a precursor to many proteins. Lysine contains an α-amino group (which is in the protonated form when the lysine is dissolved in water at physiological pH), an α-carboxylic acid group ( ...

.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 Putrefaction, putref ...

and cadaverine were first described in 1885 by the

Berlin Berlin ( ; ) is the Capital of Germany, capital and largest city of Germany, by both area and List of cities in Germany by population, population. With 3.7 million inhabitants, it has the List of cities in the European Union by population withi ...

physician

Ludwig Brieger Ludwig Brieger (1849–1919, Glatze (now Klodzko, Poland)) was a German physician, pathologist, and chemist. Biography After graduating from the gymnasium in Glatz, he studied at the University of Breslau and University of Stratsburg, wher ...

(1849–1919). It was named from the English adjective ''cadaverous''.

Receptors

zebrafish The zebrafish (''Danio rerio'') is a species of freshwater ray-finned fish belonging to the family Danionidae of the order Cypriniformes. Native to South Asia, it is a popular aquarium fish, frequently sold under the trade name zebra danio (an ...

, 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 In biology, the word gene has two meanings. The Mendelian gene is a basic unit of heredity. The molecular gene is a sequen ...

and TAAR8.

Clinical significance

Seminal plasma Seminal, ultimately from Latin ''semen'', "seed", may refer to: *Relating to seeds *Relating to semen *A work, event or person having much social influence Social influence comprises the ways in which individuals adjust their behavior to meet th ...

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 Bacterial vaginosis (BV) is an infection 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 urina ...

has been linked to cadaverine and

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 Substances discovered in the 19th century