Cadaverine: Difference between revisions

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==Clinical significance==
==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]] <ref>{{cite journal|last=Yeoman|first=CJ|coauthors=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|title=A multi-omic systems-based approach reveals metabolic markers of bacterial vaginosis and insight into the disease.|journal=PloS one|date=2013|year=2013|volume=8|issue=2|pages=e56111|doi=10.1371/journal.pone.0056111|pmid=23405259|url=http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0056111}}</ref>.
Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism.


==Toxicity==
==Toxicity==

Revision as of 14:15, 16 June 2013

Cadaverine
Skeletal formula of cadaverine
Ball and stick model of cadaverine
Names
IUPAC name
Pentane-1,5-diamine[1]
Other names
1,5-Diaminopentane
Identifiers
3D model (JSmol)
3DMet
1697256
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.664 Edit this at Wikidata
EC Number
  • 207-329-0
2310
KEGG
MeSH Cadaverine
RTECS number
  • SA0200000
UNII
UN number 2735
  • InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 checkY
    Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N checkY
  • NCCCCCN
Properties
C5H14N2
Molar mass 102.181 g·mol−1
Appearance colourless to yellow oily liquid
Odor 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
soluble
Solubility soluble in ethanol
slightly soluble in ethyl ether
log P −0.123
Acidity (pKa) 10.25, 9.13
1.458
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
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
3
2
0
Flash point 62 °C
Lethal dose or concentration (LD, LC):
2000 mg/kg (oral, rat)
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Cadaverine is a foul-smelling diamine 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.

History

Putrescine[3] and cadaverine[4] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).[5]

Production

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.[7]

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 [8].

Toxicity

Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of more than 2000 mg/kg body weight.[9]

See also

References

  1. ^ "Cadaverine - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 27 May 2012.
  2. ^ Lewis 1998, Page 212
  3. ^ Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.
  4. ^ 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.)
  5. ^ Brief biography of Ludwig Brieger (in German). Biography of Ludwig Brieger in English.
  6. ^ Wolfgang Legrum: Riechstoffe, zwischen Gestank und Duft, Vieweg + Teubner Verlag (2011) S. 65, ISBN 978-3-8348-1245-2.
  7. ^ Cadaverine PubChem
  8. ^ Yeoman, CJ (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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)CS1 maint: date and year (link) CS1 maint: unflagged free DOI (link)
  9. ^ 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.
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