Cadaverine
| Cadaverine | |
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Pentane-1,5-diamine[1] |
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Other names
1,5-Diaminopentane |
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| Identifiers | |
| CAS number | 462-94-2  |
| PubChem | 273 |
| ChemSpider | 13866593 |
| UNII | L90BEN6OLL |
| EC number | 207-329-0 |
| UN number | 2735 |
| DrugBank | DB03854 |
| KEGG | C01672 |
| MeSH | Cadaverine |
| ChEBI | CHEBI:18127 |
| ChEMBL | CHEMBL119296 |
| RTECS number | SA0200000 |
| Beilstein Reference | 1697256 |
| Gmelin Reference | 2310 |
| 3DMet | B00334 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C5H14N2 |
| Molar mass | 102.18 g mol−1 |
| Appearance | Colourless liquid |
| Density | 0.873 g/mL |
| Melting point |
9 °C, 282 K, 48 °F |
| Boiling point |
179 °C, 452.2 K, 354 °F |
| log P | −0.123 |
| Refractive index (nD) | 1.458 |
| Hazards | |
| GHS pictograms |  |
| GHS signal word | DANGER |
| GHS hazard statements | H314 |
| GHS precautionary statements | P280, P305+351+338, P310 |
| EU classification |  C |
| R-phrases | R34 |
| S-phrases | S26, S36/37/39, S45 |
| Flash point | 62 °C |
| Related compounds | |
| Related alkanamines | |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Cadaverine is a foul-smelling 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.
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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.[citation needed]
Clinical significance [edit]
Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism.
Toxicity [edit]
Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of more than 2000 mg/kg body weight.[7]
See also [edit]
References [edit]
- ^ "Cadaverine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 27 May 2012.
- ^ Lewis 1998, Page 212
- ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
- ^ 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.)
- ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
- ^ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2.
- ^ 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.
