Chemistry:Cadaverine
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| Names | |
|---|---|
| Preferred IUPAC name
Pentane-1,5-diamine | |
| Other names
1,5-Diaminopentane, pentamethylenediamine
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| Identifiers | |
3D model (JSmol)
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| 3DMet | |
| 1697256 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| EC Number |
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| 2310 | |
| KEGG | |
| MeSH | Cadaverine |
PubChem CID
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| RTECS number |
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| UNII | |
| UN number | 2735 |
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| Properties | |
| C5H14N2 | |
| Molar mass | 102.181 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Unpleasant |
| Density | 873,0 g/l |
| Melting point | 11.83[2] °C (53.29 °F; 284.98 K) |
| Boiling point | 179.1 °C; 354.3 °F; 452.2 K |
| Soluble | |
| Solubility in other solvents | conventional organic solvents |
| log P | −0.123 |
| Acidity (pKa) | 10.25, 9.13 |
Refractive index (nD)
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1.458 |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | DANGER |
| H314 | |
| P280, P305+351+338, P310 | |
| NFPA 704 (fire diamond) | |
| Flash point | 62 °C (144 °F; 335 K) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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2000 mg/kg (oral, rat) |
| Related compounds | |
Related alkanamines
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as a diamine, it is a colorless liquid with an unpleasant odor.[3] It is present in small quantities in living organisms but is often associated with the putrefaction of animal tissue.
Production
Cadaverine is produced by decarboxylation of lysine.[4] It can be synthesized by many methods including the hydrogenation of glutaronitrile and the reactions of 1,5-dichloropentane.[3]
History
Putrescine[5] and cadaverine[6] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[7]
Receptors
In zebrafish, the trace amine-associated receptor 13c (or TAAR13c) has been identified as a high-affinity receptor for cadaverine.[8] In humans, molecular modelling and docking experiments have shown that cadaverine fits into the binding pocket of the human TAAR6 and TAAR8.[9]
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.[10]
Derivatives
- Pentolinium and pentamethonium.
Toxicity
Acute oral toxicity of cadaverine is 2,000 mg/kg body weight; its no-observed-adverse-effect level is 2,000 ppm (180 mg/kg body weight/day).[11]
See also
References
- ↑ Thalladi, V.R.; Boese, R.; Weiss, H.-C. (2001). CSD Entry: QATWEN : 1,5-Pentanediamine. Cambridge Crystallographic Data Centre. doi:10.5517/cc4g861. https://dx.doi.org/10.5517/cc4g861. Retrieved 2021-11-07.
- ↑ Thalladi, V. R.; Boese, R.; Weiss, H. C. (2000). "The Melting Point Alternation in α,ω-Alkanediols and α,ω-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions". Angew. Chem. Int. Ed. 39 (5): 918–922. doi:10.1002/(SICI)1521-3773(20000303)39:5<918::AID-ANIE918>3.0.CO;2-E. PMID 10760893.
- ↑ 3.0 3.1 Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
- ↑ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN:978-3-8348-1245-2
- ↑ 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.
- ↑ 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. PMID 26519734.
- ↑ 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. doi:10.1371/journal.pcbi.1005945. PMID 29324768. Bibcode: 2018PLSCB..14E5945I.
- ↑ Yeoman, CJ; Thomas, SM; Miller, ME; Ulanov, AV; Torralba, M; Lucas, S; Gillis, M; Cregger, M et al. (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. Bibcode: 2013PLoSO...856111Y.
- ↑ 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. PMID 9207896.
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