Cadaverine

Cadaverine
IUPAC name

pentane-1,5-diamine, 1,5-diaminopentane
Identifiers
CAS number 462-94-2 Y
PubChem 273
ChemSpider 13866593 Y
UNII L90BEN6OLL Y
DrugBank DB03854
KEGG C01672 Y
MeSH Cadaverine
ChEBI CHEBI:18127 Y
ChEMBL CHEMBL119296 Y
Jmol-3D images Image 1
Properties
Molecular formula C5H14N2
Molar mass 102.178
Density 0.870 g/cm³
Melting point

9 °C
Boiling point

178–180 °C
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

Contents

History

Putrescine[2] and cadaverine[3] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[4]

Production

Cadaverine is the decarboxylation product of the amino acid lysine.

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 and semen.

Clinical significance

Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism.

Toxicity

Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of more than 2000 mg/kg body weight.[5]

See also

Notes

  1. ^ Lewis 1998, Page 212
  2. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
  3. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 39. From page 39: Ich nenne das neue Diamin C5H16N2: "Cadaverin", da ausser der empirischen Zussamsetzung, welche die neue Base als ein Hydrür des Neuridins für den flüchtigen Blick erscheinen lässt, keine Anhaltspunkte für die Berechtigung dieser Auffassung zu erheben waren. (I call the new di-amine, C5H16N2, "cadaverine," since besides its empirical composition, which allows the new base to appear superficially as a hydride of neuridine, no clues for the justification of this view arose.)
  4. ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
  5. ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats

References