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Ergotidine

Ergotidine

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Also known as: 56-92-8, Histamine 2hcl, Ceplene, Peremin, 1h-imidazole-4-ethanamine dihydrochloride, 2-(1h-imidazol-4-yl)ethanamine dihydrochloride

Molecular Formula

C₅H₁₁Cl₂N₃

Molecular Weight

184.06 g/mol

InChI Key

PPZMYIBUHIPZOS-UHFFFAOYSA-N

FDA UNII

3POA0Q644U

An amine derived by enzymatic decarboxylation of HISTIDINE. It is a powerful stimulant of gastric secretion, a constrictor of bronchial smooth muscle, a vasodilator, and also a centrally acting neurotransmitter.

1 2D Structure

Ergotidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(1H-imidazol-5-yl)ethanamine;dihydrochloride

2.1.2 InChI

InChI=1S/C5H9N3.2ClH/c6-2-1-5-3-7-4-8-5;;/h3-4H,1-2,6H2,(H,7,8);2*1H

2.1.3 InChI Key

PPZMYIBUHIPZOS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=C(NC=N1)CCN.Cl.Cl

2.2 Other Identifiers

2.2.1 UNII

3POA0Q644U

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ceplene

2. Histamine

3. Histamine Hydrochloride

4. Peremin

2.3.2 Depositor-Supplied Synonyms

1. 56-92-8

2. Histamine 2hcl

3. Ceplene

4. Peremin

5. 1h-imidazole-4-ethanamine Dihydrochloride

6. 2-(1h-imidazol-4-yl)ethanamine Dihydrochloride

7. 1h-imidazole-4-ethanamine, Dihydrochloride

8. 2-(4-imidazolyl)ethylamine Dihydrochloride

9. 2-(1h-imidazol-4-yl)ethylamine Dihydrochloride

10. Histaminedihydrochloride

11. Mfcd00012703

12. Histamine Chloride

13. Histamine Dihcl

14. Histamine Dichloride

15. Histamine Dihydrochloride [usan]

16. 2-imidazol-4-ylethylamine Dihydrochloride

17. Histaminedium Dichloride

18. Histamine Hcl

19. 4-(2-aminoethyl)imidazole Dihydrochloride

20. Histamine Dichlorhydrate

21. Histaminum Hydrochloricum

22. 2-(1h-imidazol-5-yl)ethanamine Dihydrochloride

23. Histamine (dihydrochloride)

24. 2-(1h-imidazol-4-yl)ethan-1-amine Dihydrochloride

25. Histamine, Dihydrochloride

26. 3poa0q644u

27. Nsc-257873

28. 1h-imidazole-5-ethanamine, Hydrochloride (1:2)

29. Bichlorhydrated'histamine

30. Histamine Dihydrochloride (usan)

31. 2-(1h-imidazol-4-yl)ethanamine;dihydrochloride

32. Sr-01000075270

33. Bichlorhydrate D'histamine [french]

34. Einecs 200-298-4

35. Bichlorhydrate D'histamine

36. Nsc 257873

37. Unii-3poa0q644u

38. Ai3-24394

39. Ceplene (tn)

40. Histamine Dihydrocloride

41. 2-(1h-imidazol-5-yl)ethanamine;dihydrochloride

42. C5h9n3.2hcl

43. Schembl58710

44. Spectrum1500331

45. Chembl1533310

46. Dtxsid1058767

47. Schembl16778301

48. Timtec-bb Sbb003722

49. Hms1920d11

50. Act02743

51. Bcp16313

52. Hy-b0722

53. Str02021

54. Tox21_500595

55. Ccg-38567

56. Mfcd08060928

57. S4118

58. Histamine Dihydrochloride [mi]

59. Akos015894236

60. Akos016353223

61. Ac-7507

62. Bs-3141

63. Cs-w020699

64. Histamine Hydrochloride [mart.]

65. Ks-5310

66. Lp00595

67. Histamine Hydrochloride [who-dd]

68. Histaminum Hydrochloricum [hpus]

69. Ncgc00093973-01

70. Ncgc00093973-02

71. Ncgc00093973-03

72. Ncgc00261280-01

73. 2-(4-imidazolyl)ethylaminedihydrochloride

74. 4-(2-aminoethyl)imidazole Dihydorchloride

75. Bp-12001

76. Histamine Dihydrochloride [usp-rs]

77. Sy012860

78. Db-019204

79. Histamine Dihydrochloride [ema Epar]

80. Histamine Dihydrochloride, >=99.0% (at)

81. Eu-0100595

82. Ft-0627074

83. H0146

84. Sw219552-1

85. En300-75558

86. 4-(2-aminoethyl)-1h-imidazole Dihydrochloride

87. D04444

88. Edihydrochlorideavailablefrom1kgto100kg.

89. H 7250

90. H-2250

91. H-2255

92. Histamine Dihydrochloride [ep Monograph]

93. 012h703

94. A831236

95. Histamine Dihydrochloride, >=99% (tlc), Powder

96. 1h-imidazole-4-ethanamine, Chloride (1:1)

97. 2-(1h-imidazol-5-yl)ethan-1-amine Dihydrochloride

98. Q5772985

99. Sr-01000075270-1

100. Sr-01000075270-7

101. Histamine Dihydrochloride, Tested According To Ph Eur

102. F2191-0277

103. Histamine Dihydrochloride, Saj Special Grade, >=98.0%

104. Histamine Dihydrochloride, Vetec(tm) Reagent Grade, 98%

105. Z1267773750

106. 2-(1h-imidazol-5-yl)ethanamine Dihydrochloride, Aldrichcpr

107. 2-(1h-imidazol-5-yl)ethanamine Hydrochloride (1:1)

108. Histamine Dihydrochloride 100 Microg/ml In Acetonitrile:water

109. Histamine Dihydrochloride, European Pharmacopoeia (ep) Reference Standard

110. Allergen Scratch Extract Positive Control 'torii' Histamine Dihydrochloride

111. Histamine Dihydrochloride, United States Pharmacopeia (usp) Reference Standard

112. 2-(4-imidazolyl)ethylamine Dihydrochloride; 2-(1h-imidazol-4-yl)ethylamine Dihydrochloride;histamine 2hcl

2.3.3 Other Synonyms

1. Ergamine

2. Ergotidine

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₅H₁₁Cl₂N₃
Molecular Weight	184.06 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	183.0330028 g/mol
Monoisotopic Mass	183.0330028 g/mol
Topological Polar Surface Area	54.7 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	64.7
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	3

4 Drug and Medication Information

4.1 Drug Indication

Ceplene maintenance therapy is indicated for adult patients with acute myeloid leukaemia in first remission concomitantly treated with interleukin-2 (IL-2). The efficacy of Ceplene has not been fully demonstrated in patients older than age 60.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Histamine Agonists

Drugs that bind to and activate histamine receptors. Although they have been suggested for a variety of clinical applications histamine agonists have so far been more widely used in research than therapeutically. (See all compounds classified as Histamine Agonists.)

5.2 ATC Code

L03AX14

L - Antineoplastic and immunomodulating agents

L03 - Immunostimulants

L03A - Immunostimulants

L03AX - Other immunostimulants

L03AX14 - Histamine dihydrochloride