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Cadaverine

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Title: Cadaverine  
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Subject: Polyamine, Putrescine, Alkaloid, C5H14N2, Methylhexanamine
Collection: Foul-Smelling Chemicals, Polyamines
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Cadaverine

Cadaverine
Skeletal formula of cadaverine
Ball and stick model of cadaverine
Identifiers
CAS number  YesY
PubChem
ChemSpider  YesY
UNII  YesY
EC number
UN number 2735
DrugBank
KEGG  YesY
MeSH
ChEBI  YesY
ChEMBL  YesY
RTECS number SA0200000
Beilstein Reference 1697256
Gmelin Reference 2310
3DMet
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
2
3
0
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   YesY/N?)

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.

Contents

  • History 1
  • Production 2
  • Clinical significance 3
  • Toxicity 4
  • See also 5
  • References 6
  • External links 7

History

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

Production

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

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

Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of 83 mg/kg body weight.[9]

See also

References

  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.  
  9. ^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats
  • Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press.  

External links

  • GMD MS Spectrum
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