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2D Structure
Also known as: Galanthamine hydrobromide, 1953-04-4, Reminyl, Nivalin, Nivaline, Razadyne
Molecular Formula
C17H22BrNO3
Molecular Weight
368.3  g/mol
InChI Key
QORVDGQLPPAFRS-XPSHAMGMSA-N
FDA UNII
MJ4PTD2VVW

A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;hydrobromide
2.1.2 InChI
InChI=1S/C17H21NO3.BrH/c1-18-8-7-17-6-5-12(19)9-14(17)21-16-13(20-2)4-3-11(10-18)15(16)17;/h3-6,12,14,19H,7-10H2,1-2H3;1H/t12-,14-,17-;/m0./s1
2.1.3 InChI Key
QORVDGQLPPAFRS-XPSHAMGMSA-N
2.1.4 Canonical SMILES
CN1CCC23C=CC(CC2OC4=C(C=CC(=C34)C1)OC)O.Br
2.1.5 Isomeric SMILES
CN1CC[C@@]23C=C[C@@H](C[C@@H]2OC4=C(C=CC(=C34)C1)OC)O.Br
2.2 Other Identifiers
2.2.1 UNII
MJ4PTD2VVW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Galantamin

2. Galantamine

3. Galanthamine

4. Galanthamine Hydrobromide

5. Lycoremine

6. Nivalin

7. Nivaline

8. Razadyne

9. Reminyl

2.3.2 Depositor-Supplied Synonyms

1. Galanthamine Hydrobromide

2. 1953-04-4

3. Reminyl

4. Nivalin

5. Nivaline

6. Razadyne

7. Lycoremine Hydrobromide

8. Jilkon Hydrobromide

9. Galanthamine (hydrobromide)

10. Galanthamine Hbr

11. Tamilin

12. 193146-85-9

13. Mj4ptd2vvw

14. 5n4sa4kqx9

15. (-)-galantamine Hydrobromide

16. (+/-)-galantamine Hydrobromide

17. (+/-)-galanthamine Hydrobromide

18. Galantamine Hydrobromide (racemic)

19. Galantamine Hydrobromide, (+/-)-

20. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;hydrobromide

21. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

22. Razadyne Er

23. Reminyl (tn)

24. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azoniatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-ol;bromide

25. (4as,6r,8as)-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6h-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol Hydrobromide

26. Galanthaminehydrobromide

27. 1953-04-4 (hbr); 1953-04-4 (free Base).

28. (1s,12s,14r)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6(17),7,9,15-tetraen-14-ol Hydrobromide

29. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol Hydrobromide

30. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide (1:1), (4ar,6s,8ar)-rel-

31. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide (1:1), (4as,6r,8as)-

32. Smr000449267

33. Sr-01000597844

34. Nivaline (pharmaceutical)

35. C17h22brno3

36. Anti-alzheimer

37. Sr-05000001783

38. Nivalin;razadyne

39. Galantamine Hydrobromide [usan]

40. Reminyl Xl

41. Jilcon Hydrobromide

42. Razadyne (tn)

43. Prestwick_236

44. Einecs 217-780-5

45. Galanthamine Hydrobromide From Lycoris Sp.

46. Mfcd00067672

47. Unii-mj4ptd2vvw

48. Unii-5n4sa4kqx9

49. 1953-04-4 Unlabeled

50. Chembl1555

51. Galanthamine-d3 Hydrobromide

52. Mls000758283

53. Mls001401401

54. Galanthamine Hydrobromide,(s)

55. Schembl177993

56. Spectrum1501202

57. Hms1569f18

58. Hms1921p21

59. Hy-a0009

60. Galantamine Hydrobromide (jan/usp)

61. Ac-469

62. Ccg-38829

63. Galantamine Hydrobromide [mi]

64. Galantamine Hydrobromide [usan:usp]

65. S1339

66. Galantamine Hydrobromide [jan]

67. Galanthamine-o-methyl-d3 Hydrobromide

68. Akos007930166

69. Akos015960209

70. Cs-0378

71. Fd10095

72. Galantamine Hydrobromide [hsdb]

73. Nc00061

74. Galantamine Hydrobromide [mart.]

75. Galantamine Hydrobromide [vandf]

76. Galantamine Hydrobromide [usp-rs]

77. Galantamine Hydrobromide [who-dd]

78. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4as,6r,8as)-

79. As-12155

80. Gp-37267

81. G0293

82. Galantamine Hydrobromide [orange Book]

83. D02173

84. Galantamine Hydrobromide [ep Monograph]

85. Galantamine Hydrobromide [usp Monograph]

86. Galantamine Hydrobromide Racemic [usp-rs]

87. 953g044

88. A866857

89. A903748

90. R-113675

91. Sr-01000597844-1

92. Sr-01000597844-5

93. Sr-05000001783-3

94. Q47495772

95. Z1558572528

96. Galanthamine Hydrobromide From Lycoris Sp., >=94% (tlc)

97. (4as,6r,8as)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4ah-benzo[2,3]benzofuro[4,3-cd]azepin-6-ol Hydrobromide

98. (4as,6r,8as)-3-methoxy-11-methyl-5,6,9,10,11,12-hexahydro-4ah-benzo[2,3]benzofuro[4,3-cd]azepin-6-olhydrobromide

99. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol, Hydrobromide

100. (4as,6r,8as)-4a,5,9,10,11,12-hexahydro-3-methoxy-d3-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

101. 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6h-benzofuro[3a,3,2-ef][2]benzazepin-6-ol Hydrobromide

102. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hbr (1:1), (4as,6r,8as)-

103. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hbr, (4as,6r,8as)-

104. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4a.alpha.,6.beta.,8ar*)-

105. 6h-benzofuro(3a,3,2-ef)(2)benzazepin-6-ol, 4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-, Hydrobromide, (4aalpha,6beta,8ar*)-

2.3.3 Other Synonyms

1. Galantamine

2. Galanthamine Hydrobromide

3. Lycoremin

4. Lycoremine

5. Nivalin

6. Razadyne

7. Reminyl

8. Galanthamine

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 368.3 g/mol
Molecular Formula C17H22BrNO3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count1
Exact Mass367.07831 g/mol
Monoisotopic Mass367.07831 g/mol
Topological Polar Surface Area41.9 Ų
Heavy Atom Count22
Formal Charge0
Complexity440
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameGalantamine hydrobromide
PubMed HealthGalantamine (By mouth)
Drug ClassesCentral Nervous System Agent
Drug LabelGalantamine hydrobromide is a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro [3a,3,2-ef][2]benzazepin-6-ol hydrobromide....
Active IngredientGalantamine hydrobromide
Dosage FormTablet; Capsule, extended release; Solution
Routeoral; Oral
Strengtheq 4mg base; 8mg; eq 12mg base; 4mg; 4mg/ml; 12mg; eq 16mg base; eq 24mg base; eq 8mg base
Market StatusTentative Approval; Prescription
CompanyRanbaxy; Apotex; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Sun Pharma Global; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs; Barr

2 of 4  
Drug NameRazadyne
Drug LabelRAZADYNE ER/RAZADYNE (galantamine hydrobromide) is galantamine hydrobromide, a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS ,6R,8aS )-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H...
Active IngredientGalantamine hydrobromide
Dosage FormTablet; Solution
RouteOral
Strengtheq 4mg base; eq 12mg base; 4mg/ml; eq 8mg base
Market StatusPrescription
CompanyJanssen Pharms

3 of 4  
Drug NameGalantamine hydrobromide
PubMed HealthGalantamine (By mouth)
Drug ClassesCentral Nervous System Agent
Drug LabelGalantamine hydrobromide is a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro [3a,3,2-ef][2]benzazepin-6-ol hydrobromide....
Active IngredientGalantamine hydrobromide
Dosage FormTablet; Capsule, extended release; Solution
Routeoral; Oral
Strengtheq 4mg base; 8mg; eq 12mg base; 4mg; 4mg/ml; 12mg; eq 16mg base; eq 24mg base; eq 8mg base
Market StatusTentative Approval; Prescription
CompanyRanbaxy; Apotex; Aurobindo Pharma; Sun Pharm Inds; Sandoz; Sun Pharma Global; Roxane; Watson Labs; Teva Pharms; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs; Barr

4 of 4  
Drug NameRazadyne
Drug LabelRAZADYNE ER/RAZADYNE (galantamine hydrobromide) is galantamine hydrobromide, a reversible, competitive acetylcholinesterase inhibitor. Galantamine hydrobromide is known chemically as (4aS ,6R,8aS )-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H...
Active IngredientGalantamine hydrobromide
Dosage FormTablet; Solution
RouteOral
Strengtheq 4mg base; eq 12mg base; 4mg/ml; eq 8mg base
Market StatusPrescription
CompanyJanssen Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Nootropic Agents

Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. (See all compounds classified as Nootropic Agents.)


Cholinesterase Inhibitors

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system. (See all compounds classified as Cholinesterase Inhibitors.)


Parasympathomimetics

Drugs that mimic the effects of parasympathetic nervous system activity. Included here are drugs that directly stimulate muscarinic receptors and drugs that potentiate cholinergic activity, usually by slowing the breakdown of acetylcholine (CHOLINESTERASE INHIBITORS). Drugs that stimulate both sympathetic and parasympathetic postganglionic neurons (GANGLIONIC STIMULANTS) are not included here. (See all compounds classified as Parasympathomimetics.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Cholinesterase Inhibitors [MoA]; Cholinesterase Inhibitor [EPC]