1609. Cadaverine

Nomenclature

CAS number: 462-94-2
1,5-Pentanediamine; pentamethylenediamine; animal coniine.
C5H14N2; mol wt 102.18.
C 58.77%, H 13.81%, N 27.42%.

Description and 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).

Chemical structure

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.

Derivative

Dihydrochloride.

Nomenclature

CAS number: 1476-39-7
C5H14N2.2HCl; mol wt 175.10.
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.

Caution

Skin irritant and possible sensitizer.