Cadaverine

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Cadaverine
Skeletal formula of cadaverine Pentane-1,5-diamine 200.svg
Skeletal formula of cadaverine
Ball and stick model of cadaverine Cadaverine-3D-balls.png
Ball and stick model of cadaverine
Names
Preferred IUPAC name
Pentane-1,5-diamine
Other names
1,5-Diaminopentane, pentamethylenediamine
Identifiers
3D model (JSmol)
1697256
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.664 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-329-0
2310
KEGG
MeSH Cadaverine
PubChem CID
RTECS number
  • SA0200000
UNII
UN number 2735
  • InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 Yes check.svgY
    Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N Yes check.svgY
  • NCCCCCN
Properties
C5H14N2
Molar mass 102.181 g·mol−1
AppearanceColourless liquid
Odor very unpleasant; putrid
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 solventsconventional organic solvents
log P −0.123
Acidity (pKa)10.25, 9.13
1.458
Hazards
GHS labelling:
GHS-pictogram-acid.svg
Danger
H314
P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704.svgHealth 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
3
2
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. Together with putrescine, it is largely responsible for the foul odor of putrefying flesh, but also contributes to other unpleasant odors.

Contents

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] It was named from the English adjective cadaverous.

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

Seminal plasma contains cadaverine as basic amines. [10] 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. [11]

Derivatives

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). [12]

See also

References

  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.
  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. 1 2 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. ISBN   3527306730.
  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. ↑ Jana Vitku; Lucie Kolatorova; Richard Hampl (2017). "Occurrence and reproductive roles of hormones in seminal plasma". Basic Clin Androl. 27 (19): 19. doi: 10.1186/s12610-017-0062-y . PMC   5640966 . PMID   29046808.
  11. ↑ 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.
  12. ↑ 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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