Cadaverine

Foul-smelling diamine compound From Wikipedia, the free encyclopedia

Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor.[3] It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Quick facts Names, Identifiers ...
Cadaverine
Skeletal formula of cadaverine
Skeletal formula of cadaverine
Ball and stick model of cadaverine
Ball and stick model of cadaverine
Names
Preferred IUPAC name
Pentane-1,5-diamine
Other names
1,5-Diaminopentane, pentamethylenediamine
Identifiers
3D model (JSmol)
1697256
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.664 Edit this at Wikidata
EC Number
  • 207-329-0
2310
KEGG
MeSH Cadaverine
RTECS number
  • SA0200000
UNII
UN number 2735
  • InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 checkY
    Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N checkY
  • NCCCCCN
Properties
C5H14N2
Molar mass 102.181 g·mol−1
Appearance Colourless liquid
Odor very unpleasant; putrid
Density 873,0 g/l
Melting point 11.83[2] °C (53.29 °F; 284.98 K)
Boiling point 179.1 °C; 354.3 °F; 452.2 K
Soluble
Solubility in other solvents conventional organic solvents
log P −0.123
Acidity (pKa) 10.25, 9.13
1.458
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 62 °C (144 °F; 335 K)
Lethal dose or concentration (LD, LC):
2000 mg/kg (oral, rat)
Related compounds
Related alkanamines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Production

Cadaverine is produced by decarboxylation of lysine.[4] It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.[3]

History

Putrescine[5] and cadaverine[6] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[7] It was named from the English adjective cadaverous.

Receptors

In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.[8] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.[9]

Clinical significance

Seminal plasma contains cadaverine as basic amines.[10] 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 has been linked to cadaverine and putrescine.[11]

Derivatives

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).[12]

See also

References

External links

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