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Chemistry

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Also known as: Putrescine, 1,4-butanediamine, 110-60-1, Butane-1,4-diamine, Tetramethylenediamine, Butylenediamine
Molecular Formula
C4H12N2
Molecular Weight
88.15  g/mol
InChI Key
KIDHWZJUCRJVML-UHFFFAOYSA-N
FDA UNII
V10TVZ52E4

Putrescine
A toxic diamine formed by putrefaction from the decarboxylation of arginine and ornithine.
1 2D Structure

Putrescine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
butane-1,4-diamine
2.1.2 InChI
InChI=1S/C4H12N2/c5-3-1-2-4-6/h1-6H2
2.1.3 InChI Key
KIDHWZJUCRJVML-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(CCN)CN
2.2 Other Identifiers
2.2.1 UNII
V10TVZ52E4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,4 Butanediamine

2. 1,4 Diaminobutane

3. 1,4-butanediamine

4. Putrescine

5. Tetramethylenediamine

2.3.2 Depositor-Supplied Synonyms

1. Putrescine

2. 1,4-butanediamine

3. 110-60-1

4. Butane-1,4-diamine

5. Tetramethylenediamine

6. Butylenediamine

7. Putrescin

8. 1,4-butylenediamine

9. Tetramethyldiamine

10. 1,4-tetramethylenediamine

11. Putrescina

12. Putreszin

13. Tetramethylendiamin

14. Mfcd00008235

15. Nsc 60545

16. Brn 0605282

17. H2n(ch2)4nh2

18. Ai3-25444

19. 1,4-diamino-n-butane

20. Nsc-60545

21. Putrescine; Nsc 60545; Putramine

22. Chembl46257

23. V10tvz52e4

24. Chebi:17148

25. Put

26. Ccris 6751

27. Einecs 203-782-3

28. Unii-v10tvz52e4

29. Butylene Amine

30. Hsdb 7865

31. Tetramethylendiamine

32. 4-amino-butyl-amine

33. Tetramethylene Diamine

34. 1,4 Diamino Butane

35. 1,4-butane Diamine

36. 1,4-diamino Butane

37. Putrescine, Free Base

38. Spectrum_001646

39. 1i7c

40. 1i7m

41. Putrescine [mi]

42. Spectrum2_001935

43. Spectrum3_001198

44. Spectrum4_000237

45. Spectrum5_001005

46. Lopac-p-7505

47. Bmse000109

48. Bmse000814

49. Bmse000862

50. Ec 203-782-3

51. 1,4-diaminobutane, 99%

52. Butane,1,4-diamino

53. Lopac0_000972

54. Bspbio_002875

55. Kbiogr_000933

56. Kbioss_002126

57. Divk1c_000716

58. Spbio_001969

59. .alpha.,.omega.-butanediamine

60. 1,4-diaminobutane-[13c4]

61. Putrescine, Analytical Standard

62. Gtpl2388

63. Dtxsid4041107

64. Kbio1_000716

65. Kbio2_002126

66. Kbio2_004694

67. Kbio2_007262

68. Kbio3_002375

69. 1a99

70. Ninds_000716

71. Hy-n2407

72. Nsc60545

73. Zinc5828633

74. Bbl027703

75. Bdbm50009385

76. S5825

77. Stl372697

78. Akos000119071

79. Ccg-205052

80. Db01917

81. Sdccgmls-0066929.p001

82. Sdccgsbi-0050945.p003

83. Idi1_000716

84. Ncgc00015837-01

85. Ncgc00015837-02

86. Ncgc00015837-03

87. Ncgc00015837-07

88. Ncgc00162302-01

89. Bp-21408

90. Nci60_004431

91. Cs-0022608

92. D0239

93. Ft-0606836

94. 1,4-diaminobutane, Purum, >=98.0% (gc)

95. C00134

96. C02896

97. F17678

98. P-7990

99. 1,4-diaminobutane, Puriss., >=99.0% (gc)

100. Q410190

101. F1791-1258

102. Z1245649995

103. A4738f6f-f1a1-4b30-bf38-866d5ac66c93

104. 58i

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 88.15 g/mol
Molecular Formula C4H12N2
XLogP3-0.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass88.100048391 g/mol
Monoisotopic Mass88.100048391 g/mol
Topological Polar Surface Area52 Ų
Heavy Atom Count6
Formal Charge0
Complexity17.5
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)


4.2 Metabolism/Metabolites

Putrescine is synthesized biologically via two different pathways, both starting from arginine. In one pathway, arginine is converted into agmatine, with a reaction catalyzed by the enzyme arginine decarboxylase (ADC); then agmatine is transformed into carbamilputrescine by agmatine imino hydroxylase (AIH). Finally, carbamilputrescine is converted into putrescine. In the second pathway, arginine is converted into ornithine and then ornithine is converted into putrescine by ornithine decarboxylase (ODC).

ChemieDe; Putresine. In Encyclopedia of Chemistry. Available from, as of November 19, 2010: https://www.chemie.de/lexikon/e/Putrescine/


Putrescine attacks s-adenosyl methionine and converts it to spermidine. Spermidine in turn ... /reacts with/ attacks another s-adenosyl methionine and converts it to spermine.

ChemieDe; Putresine. In Encyclopedia of Chemistry. Available from, as of November 19, 2010: https://www.chemie.de/lexikon/e/Putrescine/


Putrescine is synthesized in small quantities by healthy living cells by the action of ornithine decarboxylase. The polyamines, of which putrescine is one of the simplest, appear to be growth factors necessary for cell division.

ChemieDe; Putresine. In Encyclopedia of Chemistry. Available from, as of November 19, 2010: https://www.chemie.de/lexikon/e/Putrescine/


A novel bacterial putrescine utilization pathway was discovered. Seven genes, the functions of whose products were not known, are involved in this novel pathway. Five of them encode enzymes that catabolize putrescine; one encodes a putrescine importer, and the other encodes a transcriptional regulator. This novel pathway involves six sequential steps as follows: 1) import of putrescine; 2) ATP-dependent gamma-glutamylation of putrescine; 3) oxidization of gamma-glutamylputrescine; 4) dehydrogenation of gamma-glutamyl-gamma-aminobutyraldehyde; 5) hydrolysis of the gamma-glutamyl linkage of gamma-glutamyl-gamma-aminobutyrate; and 6) transamination of gamma-aminobutyrate to form the final product of this pathway, succinate semialdehyde, which is the precursor of succinate.

PMID:15590624 Kurihara S et al; J Biol Chem 280 (6): 4602-8 (2005)


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