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.
Names | |
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Preferred IUPAC name
Pentane-1,5-diamine | |
Other names
1,5-Diaminopentane, pentamethylenediamine
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Identifiers | |
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3D model (JSmol)
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3DMet |
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1697256 | |
ChEBI |
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ChEMBL |
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ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.006.664 |
EC Number |
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2310 | |
KEGG |
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MeSH | Cadaverine |
PubChem CID
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RTECS number |
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UNII |
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UN number | 2735 |
CompTox Dashboard (EPA)
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Properties | |
C5H14N2 | |
Molar mass | 102.181 g·mol−1 |
Appearance | Colourless liquid |
Odor | Unpleasant |
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 |
Refractive index (nD)
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1.458 |
Hazards | |
GHS labelling: | |
Danger | |
H314 | |
P280, P305+P351+P338, P310 | |
NFPA 704 (fire diamond) | |
Flash point | 62 °C (144 °F; 335 K) |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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2000 mg/kg (oral, rat) |
Related compounds | |
Related alkanamines
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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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]
Putrescine[5] and cadaverine[6] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[7]
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]
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.[10]
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).[11]