Cadaverine

Cadaverine
Names
IUPAC name
Pentane-1,5-diamine[1]
Other names
1,5-Diaminopentane
Identifiers
462-94-2 YesY
3DMet B00334
1697256
ChEBI CHEBI:18127 YesY
ChEMBL ChEMBL119296 YesY
ChemSpider 13866593 YesY
DrugBank DB03854 YesY
EC Number 207-329-0
2310
Jmol 3D model Interactive image
KEGG C01672 YesY
MeSH Cadaverine
PubChem 273
RTECS number SA0200000
UNII L90BEN6OLL YesY
UN number 2735
Properties
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
soluble
Solubility soluble in ethanol
slightly soluble in ethyl ether
log P −0.123
Acidity (pKa) 10.25, 9.13
1.458
Hazards
GHS pictograms
GHS signal word DANGER
H314
P280, P305+351+338, P310
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
2
3
0
Flash point 62 °C (144 °F; 335 K)
Lethal dose or concentration (LD, LC):
2000 mg/kg (oral, rat)
Related compounds
Related alkanamines
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
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

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] This can be done at home by heating lysine with a small amount of Sodium bicarbonate mixed in. The produced gas should be led to a glass container which is surrounded by ice water. The heating must be done in a glass container, as metals may contaminate the process. Heating will produce hydrochloric acid, which is neutralized by the Sodium bicarbonate.

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 has a low acute oral toxicity of 2000 mg/kg body weight, with no-observed-adverse-effect level of 2000 ppm (180 mg/kg body weight/day).[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. doi:10.1371/journal.pone.0056111. PMID 23405259.
  9. ↑ Til, H.P.; Falke, H.E.; Prinsen, M.K.; Willems, M.I. (1997). "Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats". Food and Chemical Toxicology 35 (3-4): 337–348. doi:10.1016/S0278-6915(97)00121-X. ISSN 0278-6915.

External links

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