Cadaverine

Cadaverine
	File:Cadaverine-2D-skeletal.png
Names
	IUPAC name pentane-1,5-diamine
Identifiers
CAS Number	462-94-2 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL119296 ;
ChemSpider	13866593 ;
ECHA InfoCard	100.006.664
KEGG	C01672 ;
MeSH	Cadaverine
PubChem CID	273;
CompTox Dashboard (EPA)	DTXSID5075448 ;
	InChI InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N ; InChI=1/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 Key: VHRGRCVQAFMJIZ-UHFFFAOYAX;
	SMILES NCCCCCN;
Properties
Chemical formula	C5H14N2
Molar mass	102.178
Density	0.870 g/cm³
Melting point	9 °C
Boiling point	178-180 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cadaverine is a foul-smelling compound produced by protein hydrolysis during putrefaction of animal tissue. Cadaverine is a toxic^[1] 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^[2] and cadaverine^[3] were first described in 1885 by the Berlin physician Ludwig Brieger (1849–1919).^[4]

Production

Cadaverine is the decarboxylation product of the amino acid lysine.

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 and semen.

Clinical significance

Elevated levels of cadaverine have been found in the urine of some patients with defects in lysine metabolism.

Toxicity

Cadaverine is toxic in large doses. In rats it had an acute oral toxicity of more than 2000 mg/kg body weight.^[5]

Notes

^ 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).
^ Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats

References

Lewis, Robert Alan (1998). Lewis' Dictionary of Toxicology. CRC Press. ISBN 1566702232.

[1] Lewis 1998, Page 212

[2] Ludwig Brieger, "Weitere Untersuchungen über Ptomaine" [Further investigations into ptomaines] (Berlin, Germany: August Hirschwald, 1885), page 43.

[3] 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.)

[4] Brief biography of Ludwig Brieger (in German).

[5] Acute and subacute toxicity of tyramine, spermidine, spermine, putrescine and cadaverine in rats

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