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Synopsis

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Chemistry

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Also known as: 71-44-3, Musculamine, Neuridine, Gerontine, Spermin, 4,9-diaza-1,12-dodecanediamine

Molecular Formula

C₁₀H₂₆N₄

Molecular Weight

202.34 g/mol

InChI Key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

FDA UNII

2FZ7Y3VOQX

A biogenic polyamine formed from spermidine. It is found in a wide variety of organisms and tissues and is an essential growth factor in some bacteria. It is found as a polycation at all pH values. Spermine is associated with nucleic acids, particularly in viruses, and is thought to stabilize the helical structure.

1 2D Structure

Spermine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N,N'-bis(3-aminopropyl)butane-1,4-diamine

2.1.2 InChI

InChI=1S/C10H26N4/c11-5-3-9-13-7-1-2-8-14-10-4-6-12/h13-14H,1-12H2

2.1.3 InChI Key

PFNFFQXMRSDOHW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C(CCNCCCN)CNCCCN

2.2 Other Identifiers

2.2.1 UNII

2FZ7Y3VOQX

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 71-44-3

2. Musculamine

3. Neuridine

4. Gerontine

5. Spermin

6. 4,9-diaza-1,12-dodecanediamine

7. N,n'-bis(3-aminopropyl)-1,4-butanediamine

8. Diaminopropyltetramethylenediamine

9. Spermine, Puriss

10. 1,4-butanediamine, N,n'-bis(3-aminopropyl)-

11. 4,9-diazadodecamethylenediamine

12. N,n'-bis(3-aminopropyl)butane-1,4-diamine

13. 1,4-bis(aminopropyl)butanediamine

14. Gerotine

15. 4,9-diazadodecane-1,12-diamine

16. 68956-56-9

17. Polyspermine

18. Nsc 268508

19. 1,4-bis(aminopropyl) Butanediamine

20. N1,n1'-(butane-1,4-diyl)bis(propane-1,3-diamine)

21. Spermine Free Base

22. Actilip Sp-91

23. 1,4-diaminobutane, N,n'-bis(3-aminopropyl)-

24. Brn 1750791

25. Ai3-26633

26. 1,5,10,14-tetraazatetradecane

27. 2fz7y3voqx

28. Nsc-268508

29. Nsc 268508; Neuridine

30. Chembl23194

31. Hydrocarbons, Terpene Processing By-products

32. 71052-31-8

33. Chebi:15746

34. N1,n4-bis(3-aminopropyl)-1,4-butanediamine

35. Nsc268508

36. 71-44-3 (free Base)

37. Spermidine 3hcl

38. 1,4-butanediamine, N1,n4-bis(3-aminopropyl)-

39. Spm

40. (3-aminopropyl)({4-[(3-aminopropyl)amino]butyl})amine

41. 1,4-butanediamine, N1,n4-bis(3-aminopropyl)-, Homopolymer

42. Spermina

43. Mls002472980

44. Diaminopropyl-tetramethylenediamine

45. Spermina [italian]

46. Smr001397086

47. Einecs 200-754-2

48. Unii-2fz7y3voqx

49. Mfcd00008215

50. Spermine Puriss

51. N,n'-bis(3-aminopropyl)-1,4-diaminobutane

52. Terpene Hydrocarbons, By Product

53. Einecs 273-309-3

54. 4,12-diamine

55. Spermine, >=97%

56. Tocris-0958

57. Gerotine [inci]

58. Spermine [mi]

59. Lopac-s-2876

60. Biomol-nt_000213

61. Bmse000117

62. Ec 273-309-3

63. Ncimech_000206

64. Spermine, Min. 98.0%

65. Lopac0_001077

66. Schembl14965

67. Wln: Z3m4m3z

68. Gtpl710

69. Spermine, Analytical Standard

70. 4-04-00-01301 (beilstein Handbook Reference)

71. Bpbio1_001086

72. Sperminetetrahydrochloride

73. Dtxsid9058781

74. Bdbm79403

75. Cid_5351186

76. 1, N,n'-bis(3-aminopropyl)-

77. Spermine, >=99.0% (gc)

78. Hy-b1777

79. Zinc1532734

80. Ccg-35276

81. Hsci1_000212

82. S3948

83. Akos024258603

84. Db00127

85. Sb38410

86. Sdccgsbi-0051047.p003

87. N1,n4-bis(3-aminopropyl)-butanediamine

88. Ncgc00015941-01

89. Ncgc00015941-02

90. Ncgc00015941-03

91. Ncgc00015941-04

92. Ncgc00015941-05

93. Ncgc00015941-10

94. Ncgc00024902-01

95. Ncgc00024902-02

96. Ncgc00024902-03

97. As-35114

98. Bp-21388

99. Nci60_035280

100. Db-055526

101. Cs-0013806

102. Ft-0625219

103. Ft-0631308

104. N,na?bis(3-aminopropyl)-1,4-diaminobutane

105. Spermine, Vetec(tm) Reagent Grade, >=97%

106. N,n''-bis(3-aminopropyl)butane-1,4-diamine

107. C00750

108. S-7400

109. Z-1049

110. 956s569

111. A866441

112. L001114

113. N1,n1'-(butane-1,4-diyl)dipropane-1,3-diamine

114. Q424597

115. N,n'-bis(3-aminopropyl)-1,4-tetramethylenediamine

116. N1,n1-(butane-1,4-diyl)bis(propane-1,3-diamine)

117. N1,n1'-(butane-1,4-diyl);bis(propane-1,3-diamine);

118. 2b445aed-6284-43e4-82fe-39598858d67f

119. 3-aminopropyl-[4-(3-aminopropylamino)butyl]amine;hydrochloride

120. N,n''''-bis(3-aminopropyl)butane-1,4-diamine;hydrochloride

121. N,n''''-bis(3-azanylpropyl)butane-1,4-diamine;hydrochloride

122. Spermine, Bioreagent, Amorphous Semi-solid, Suitable For Cell Culture

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₆N₄
Molecular Weight	202.34 g/mol
XLogP3	-1.1
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	11
Exact Mass	202.21574685 g/mol
Monoisotopic Mass	202.21574685 g/mol
Topological Polar Surface Area	76.1 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	86.1
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For nutritional supplementation, also for treating dietary shortage or imbalance

5 Pharmacology and Biochemistry

5.1 Pharmacology

Spermine is a polyamine. It is an organic molecule that is involved in cellular metabolism.

5.2 Mechanism of Action

Spermine is derived from spermidine by spermine synthase. Spermine is a polyamine, a small organic cations that is absolutely required for eukaryotic cell growth. Spermine, is normally found in millimolar concentrations in the nucleus. Spermine functions directly as a free radical scavenger, and forms a variety of adducts that prevent oxidative damage to DNA. Oxidative damage to DNA by reactive oxygen species is a continual problem that cells must guard against to survive. Hence, spermine is a major natural intracellular compound capable of protecting DNA from free radical attack. Spermine is also implicated in the regulation of gene expression, the stabilization of chromatin, and the prevention of endonuclease-mediated DNA fragmentation.

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