Cadaverine

Title: Cadaverine
CAS Registry Number: 462-94-2
CAS Name: 1,5-Pentanediamine
Additional Names: pentamethylenediamine; animal coniine
Molecular Formula: C5H14N2
Molecular Weight: 102.18
Percent Composition: C 58.77%, H 13.81%, N 27.42%
Line Formula: NH2(CH2)5NH2
Literature References: Biogenic polyamine and homolog of putrescine, q.v., produced by decarboxylation of lysine. Found in cholera discharge. Isoln: Bocklisch, Ber. 18, 1922 (1885); Ackermann, Z. Physiol. Chem. 54, 16 (1907). Prepn: Ladenburg, Ber. 18, 2956 (1885). GC determn in foods: W. F. Staruszkiewicz, J. F. Bond, J. Assoc. Off. Anal. Chem. 64, 584 (1981). Metabolism study of 14C-cadaverine in rat brain: S. K. Salzman, M. Stepita-Klauco, J. Neurochem. 37, 1308 (1981). Biosynthetic study in S. ruminantium: Y. Kamio et al., J. Biol. Chem. 257, 3326 (1982).
Properties: Colorless, syrupy liquid; characteristic odor. Strong base, fumes and attracts CO2 on exposure to air. pKa1 10.25; pKa2 9.13. Poisonous! d425 0.873. mp 9°. bp 178-180°. nD20 1.463. Sol in water, alcohol; slightly sol in ether. Keep well closed.
Melting point: mp 9°
Boiling point: bp 178-180°
pKa: pKa1 10.25; pKa2 9.13
Index of refraction: nD20 1.463
Density: d425 0.873
Derivative Type: Dihydrochloride
Molecular Formula: C5H14N2.2HCl
Molecular Weight: 175.10
Percent Composition: C 34.30%, H 9.21%, N 16.00%, Cl 40.49%
Properties: Needles from water, mp 225-230°. Sol in water. Practically insol in abs alc.
Melting point: mp 225-230°
CAUTION: Skin irritant and possible sensitizer.
Cadexomer Iodine Cadherins Cadinenes Cadmium Acetate Cadmium Bromide

Cadaverine
Skeletal formula of cadaverine
Ball and stick model of cadaverine
Identifiers
CAS number 462-94-2 YesY
PubChem 273
ChemSpider 13866593 YesY
UNII L90BEN6OLL YesY
EC number 207-329-0
UN number 2735
DrugBank DB03854
KEGG C01672 YesY
MeSH Cadaverine
ChEBI CHEBI:18127 YesY
ChEMBL CHEMBL119296 YesY
RTECS number SA0200000
Beilstein Reference 1697256
Gmelin Reference 2310
3DMet B00334
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water soluble
Solubility soluble in ethanol
slightly soluble in ethyl ether
log P −0.123
Acidity (pKa) 10.25, 9.13
Refractive index (nD) 1.458
Hazards
GHS pictograms The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H314
GHS precautionary statements P280, P305+351+338, P310
EU classification Corrosive C
R-phrases R34
S-phrases S26, S36/37/39, S45
NFPA 704
NFPA 704.svg
2
3
0
Flash point 62 °C; 144 °F; 335 K
LD50 2000 mg/kg (oral, rat)
Related compounds
Related alkanamines
  • n-Butylamine
  • sec-Butylamine
  • Putrescine
  • Pentylamine
  • Methylhexanamine
  • Hexamethylenediamine
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cadaverine is a foul-smelling diamine compound produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic[2] diamine with the formula NH2(CH2)5NH2, which is similar to putrescine. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine.