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Cadaverine

Cadaverine
Skeletal formula of cadaverine
Ball and stick model of cadaverine
Names
Preferred IUPAC name
Pentane-1,5-diamine
Other names
1,5-Diaminopentane
Identifiers
462-94-2 YesY
3D model (Jmol) Interactive image
3DMet B00334
1697256
ChEBI CHEBI:18127 YesY
ChEMBL ChEMBL119296 YesY
ChemSpider 13866593 YesY
DrugBank DB03854 YesY
ECHA InfoCard 100.006.664
EC Number 207-329-0
2310
KEGG C01672 YesY
MeSH Cadaverine
PubChem 273
RTECS number SA0200000
UNII L90BEN6OLL YesY
UN number 2735
Properties
C5H14N2
Molar mass 102.18 g·mol−1
Appearance colourless to yellow oily liquid
Odor unpleasant
Density 0.8730 g/mL
Melting point 11.83 °C (53.29 °F; 284.98 K)
Boiling point 179.1 °C; 354.3 °F; 452.2 K
soluble
Solubility soluble in ethanol
slightly soluble in ethyl ether
log P −0.123
Acidity (pKa) 10.25, 9.13
1.458
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H314
P280, P305+351+338, P310
Corrosive C
R-phrases R34
S-phrases S26, S36/37/39, S45
NFPA 704
Flammability code 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 fuel Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 62 °C (144 °F; 335 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 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).
YesY  (what is YesYN ?)
Infobox references

Cadaverine is a foul-smelling diamine compound produced by the putrefaction of animal tissue. Cadaverine is a toxicdiamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine.

Putrescine and cadaverine were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).

Cadaverine is the decarboxylation product of the amino acid lysine. This can be done at home by heating lysine with a small amount of Sodium bicarbonate mixed in. The produced gas should be led to a glass container which is surrounded by ice water. The heating must be done in a glass container, as metals may contaminate the process.

However, this diamine is not purely associated with putrefaction. It is also produced in small quantities by living beings. It is partially responsible for the distinctive odors of urine.

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.

Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).


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