Cadaverine

Cadaverine is a foul-smelling diamine compound produced by the putrefaction of animal tissue. Cadaverine is a toxic[1] diamine with the formula NH2(CH2)5NH2, which is similar to putrescine's NH2(CH2)4NH2. Cadaverine is also known by the names 1,5-pentanediamine and pentamethylenediamine.

Cadaverine
Names
Preferred IUPAC name
Pentane-1,5-diamine
Other names
1,5-Diaminopentane
Identifiers
CAS Number
3D model (JSmol)
3DMet
Beilstein Reference
 1697256
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.664
EC Number
  • 207-329-0
Gmelin Reference
 2310
KEGG
MeSH Cadaverine
PubChem CID
RTECS number
  • SA0200000
UNII
UN number 2735
Properties
Chemical formula
 C5H14N2
Molar mass 102.181 g·mol−1
Appearance Colourless to yellow oily liquid
Odor Unbearably unpleasant to 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 in other solvents 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
GHS Signal word Danger
GHS hazard statements
 H314
GHS precautionary statements
 P280, P305+351+338, P310
NFPA 704 (fire diamond)
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 fuelHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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).
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Infobox references

History

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

Receptors

In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverin.[5] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.[6]

Production

Cadaverine is the decarboxylation product of the amino acid lysine.[7] This can be done 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.

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.[8]

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.[9]

Derivatives
  • Pentolinium and pentamethonium are both chemical derivatives of cadaverine.

Toxicity

Cadaverine is toxic in large doses. In rats it has a low acute oral toxicity of 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).[10]

See also

References
  1. Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. p. 212. ISBN 1-56670-223-2.
  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 Archived 2011-10-03 at the Wayback Machine (in German). Biography of Ludwig Brieger in English.
  5. Li, Q; Tachie-Baffour, Y; Liu, Z; Baldwin, MW; Kruse, AC; Liberles, SD (2015). "Non-classical amine recognition evolved in a large clade of olfactory receptors". eLife. 4: e10441. doi:10.7554/eLife.10441. PMC 4695389. PMID 26519734.
  6. Izquierdo, C; Gomez-Tamayo, JC; Nebel, J-C; Pardo, L; Gonzalez, A (2018). "Identifying human diamine sensors for death related putrescine and cadaverine molecules". PLOS Computational Biology. 14 (1): e1005945. Bibcode:2018PLSCB..14E5945I. doi:10.1371/journal.pcbi.1005945. PMC 5783396. PMID 29324768.
  7. Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2.
  8. Cadaverine PubChem
  9. 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. Bibcode:2013PLoSO...856111Y. doi:10.1371/journal.pone.0056111. PMC 3566083. PMID 23405259.
  10. 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.
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