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MolPort-002-317-350
Also known as: Pentane-1,5-diamine, 1,5-diaminopentane, 462-94-2, 1,5-pentanediamine, Pentamethylenediamine, Cadaverin
Molecular Formula
C5H14N2
Molecular Weight
102.18  g/mol
InChI Key
VHRGRCVQAFMJIZ-UHFFFAOYSA-N
FDA UNII
L90BEN6OLL

A foul-smelling diamine formed by bacterial DECARBOXYLATION of LYSINE. It is also an intermediate secondary metabolite in lysine-derived alkaloid biosynthetic pathways (e.g., QUINOLIZIDINES and LYCOPODIUM).
1 2D Structure

MolPort-002-317-350

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
pentane-1,5-diamine
2.1.2 InChI
InChI=1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
2.1.3 InChI Key
VHRGRCVQAFMJIZ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CCN)CCN
2.2 Other Identifiers
2.2.1 UNII
L90BEN6OLL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,5 Pentanediamine

2. 1,5-pentanediamine

3. Biodex 1

4. Pentamethylenediamine

2.3.2 Depositor-Supplied Synonyms

1. Pentane-1,5-diamine

2. 1,5-diaminopentane

3. 462-94-2

4. 1,5-pentanediamine

5. Pentamethylenediamine

6. Cadaverin

7. 1,5-pentamethylenediamine

8. Animal Coniine

9. Ai3-26937

10. Brn 1697256

11. 1,5-diamino-n-pentane

12. L90ben6oll

13. Chembl119296

14. Chebi:18127

15. N2p

16. Pentamethylenediamine Dihydrochloride

17. Einecs 207-329-0

18. Unii-l90ben6oll

19. Hsdb 7866

20. Cadaverine, 95%

21. Mfcd00008239

22. Pentane-1,5-damne

23. 1,5-diamino-pentane

24. Biodex 1-

25. 1,5-amylene Diamine

26. Cadaverine [mi]

27. 5-azaniumylpentylammonium

28. Alpha,omega-pentanediamine

29. Bmse000072

30. Ec 207-329-0

31. Schembl21367

32. 4-04-00-01310 (beilstein Handbook Reference)

33. Cadaverine, Analytical Standard

34. H2n(ch2)5nh2

35. Schembl5495920

36. Dtxsid5075448

37. Zinc1529253

38. Bbl027704

39. Bdbm50323741

40. Stl372961

41. Akos005169829

42. Am61576

43. Cadaverine, Purum, >=97.0% (gc)

44. Ccg-266036

45. Db03854

46. Ncgc00166285-01

47. As-30673

48. Db-051367

49. Ft-0600435

50. C01672

51. 462d942

52. A827022

53. Q161555

54. J-523897

55. 1948270a-6d1b-4f40-bc13-9b680ed17b17

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 102.18 g/mol
Molecular Formula C5H14N2
XLogP3-0.6
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass102.115698455 g/mol
Monoisotopic Mass102.115698455 g/mol
Topological Polar Surface Area52 Ų
Heavy Atom Count7
Formal Charge0
Complexity25.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

The urinary excretion of histamine, methylhistamine, putrescine, cadaverine, spermidine and spermine was examined before, during and after pregnancy in rats. During the last third of undisturbed pregnancy a distinct and steep rise occurred in the excretion of all amines studied except spermine. The peak values were found a few days before the birth of the young. In spermidine excretion a second peak was observed one or two days after delivery. Before and during the first 2 weeks of gestation on a molar basis putrescine excretion was the greatest one. During the last trimester histamine was excreted in the largest amount. Under the influence of the diamine oxidase inhibitor aminoguanidine the general pattern of excretion of diamines and polyamines in pregnant rats remained essentially unchanged but the total amount excreted increased. Most conspicuous was the great elevation of urinary contents of putrescine and cadaverine.

PMID:745086 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1281758 Andersson AC et al; J Physiol 285: 311-24 (1978)


Cadaverine has been shown to be present in the central nervous system (CNS) ... Its concentration in the whole brain varies during behavioral sleep in mammals and during hibernation in molluscs. ... Cadaverine has been considered a non-metabolite of the brain, and its presence in the body was believed to be due almost entirely to bacterial decarboxylation of lysine in the intestine. In slices of mouse brain, exogenous cadaverine accumulates against a concentration gradient and can reach a concentration ten times greater in the tissue than in the surrounding medium. The question has been therefore: does the cadaverine in the brain originate from an exogenous source; is it formed and resorbed in the intestine? Assaying cadaverine in axenic mice, /it has been/ found that this is not the case, and that there is an endogenous source of cadaverine in the mouse.

Matej S-K, Dolezalova H; Nature 252: 158-9 (1974)


4.2 Metabolism/Metabolites

It is a precursor of piperidine, which has been linked with some functional stages of the CNS. Cadaverine is the source of much of the piperidine excreted in the urine.

Matej S-K, Dolezalova H; Nature 252: 158-9 (1974)


Cadaverine ... a relatively nontoxic ptomaine, C5H14N2, formed by decarboxylation of lysine; it is sometimes one of the products of Vibrio proteus and of V. cholerae, and occasionally found in the urine in cystinuria, where it causes an unpleasant odor.

Merck Source; Resource Library Powered by Dorland's Medical Dictionary for Healthcare Consumers. Available from, as of November 19, 2010: https://www.mercksource.com/pp/us/cns/cns_hl_dorlands_split.jsp?pg=/ppdocs/us/common/dorlands/dorland/misc/dmd-a-b-000.htm


Cadaverine is synthesized from lysine in a one-step reaction with lysine decarboxylase (LDC).

ChemEurope.com; Polyamine. In Encyclopedia of Chemistry. Available from, as of November 19, 2010: https://www.chemeurope.com/lexikon/e/Polyamine/


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