Cadaverine

Cadaverine
	; Skeletal formula
	; Ball-and-stick model
Names
	Preferred IUPAC name Pentane-1,5-diamine
	Other names 1,5-Diaminopentane, pentamethylenediamine
Identifiers
CAS Number	462-94-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1697256
ChEBI	CHEBI:18127 ;
ChEMBL	ChEMBL119296 ;
ChemSpider	13866593 ;
DrugBank	DB03854 ;
ECHA InfoCard	100.006.664
EC Number	207-329-0;
Gmelin Reference	2310
KEGG	C01672 ;
MeSH	Cadaverine
PubChem CID	273;
RTECS number	SA0200000;
UNII	L90BEN6OLL ;
UN number	2735
CompTox Dashboard (EPA)	DTXSID5075448 ;
	InChI InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2 Key: VHRGRCVQAFMJIZ-UHFFFAOYSA-N ;
	SMILES NCCCCCN;
Properties
Chemical formula	C5H14N2
Molar mass	102.181 g·mol−1
Appearance	Colourless liquid
Odor	Unpleasant
Density	873,0 g/l
Melting point	11.83 °C (53.29 °F; 284.98 K)
Boiling point	179.1 °C; 354.3 °F; 452.2 K
Solubility in water	Soluble
Solubility in other solvents	conventional organic solvents
log P	−0.123
Acidity (pKa)	10.25, 9.13
Refractive index (nD)	1.458
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	3 2 0
Flash point	62 °C (144 °F; 335 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	2000 mg/kg (oral, rat)
Related compounds
Related alkanamines	n-Butylamine; Putrescine; Pentylamine; Hexamethylenediamine;
	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 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.

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

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).^[12]

References

^ 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.
^ 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.
^ ^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. ISBN 3527306730.
^ 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 Archived 2011-10-03 at the Wayback Machine (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. PMC 4695389. 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. Bibcode:2018PLSCB..14E5945I. doi:10.1371/journal.pcbi.1005945. PMC 5783396. PMID 29324768.
^ 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.
^ 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.
^ 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

Media related to Pentamethylenediamine at Wikimedia Commons
GMD MS Spectrum

[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.

[Ull-3] 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.

[Legrum-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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