Cadaverine

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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
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)
LD50 2000 mg/kg (oral, rat)
Related compounds
Related alkanamines
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

History[edit]

Putrescine[3] and cadaverine[4] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[5]

Production[edit]

Cadaverine is the decarboxylation product of the amino acid lysine.[6]

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.[7]

Clinical significance[edit]

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.[8]

Toxicity[edit]

Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of more than 2000 mg/kg body weight.[9]

See also[edit]

References[edit]

  1. ^ "Cadaverine – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 27 May 2012. 
  2. ^ Lewis 1998, Page 212
  3. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
  4. ^ 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.)
  5. ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
  6. ^ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2.
  7. ^ Cadaverine PubChem
  8. ^ Yeoman, CJ; Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M; Gomez, A; Ho, M; Leigh, SR; Stumpf, R; Creedon, DJ; Smith, MA; Weisbaum, JS; Nelson, KE; Wilson, BA; White, BA (2013). "A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.". PloS one 8 (2): e56111. doi:10.1371/journal.pone.0056111. PMID 23405259. 
  9. ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats
  • Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. ISBN 1-56670-223-2. 

External links[edit]