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Skeletal formula of cadaverine
Ball and stick model of cadaverine
Preferred IUPAC name
Other names
1,5-Diaminopentane, pentamethylenediamine
3D model (JSmol)
ECHA InfoCard 100.006.664 Edit this at Wikidata
EC Number
  • 207-329-0
MeSH Cadaverine
RTECS number
  • SA0200000
UN number 2735
  • InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 checkY
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
Solubility in other solvents conventional organic solvents
log P −0.123
Acidity (pKa) 10.25, 9.13
GHS labelling:
GHS05: Corrosive
P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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 fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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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Cadaverine is an organic compound with the formula (CH2)5(NH2)2. Classified as 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.


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]


Putrescine[5] and cadaverine[6] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[7]


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[edit]

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]



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[edit]


  1. ^ Thalladi, V.R.; Boese, R.; Weiss, H.-C. (2001). "CSD Entry: QATWEN : 1,5-Pentanediamine". Cambridge Structural Database: Access Structures. Cambridge Crystallographic Data Centre. doi:10.5517/cc4g861. Retrieved 2021-11-07.
  2. ^ 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. ^ a b Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_001.
  4. ^ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2
  5. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
  6. ^ 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.)
  7. ^ Brief biography of Ludwig Brieger Archived 2011-10-03 at the Wayback Machine (in German). Biography of Ludwig Brieger in English.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.

External links[edit]