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2D Structure
Also known as: Neostigmine methyl sulfate, 51-60-5, Syntostigmin, Normastigmin, Hodostin, Neostigmine methylsulphate
Molecular Formula
C13H22N2O6S
Molecular Weight
334.39  g/mol
InChI Key
OSZNNLWOYWAHSS-UHFFFAOYSA-M
FDA UNII
98IMH7M386

A cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike PHYSOSTIGMINE, does not cross the blood-brain barrier.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;methyl sulfate
2.1.2 InChI
InChI=1S/C12H19N2O2.CH4O4S/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5;1-5-6(2,3)4/h6-9H,1-5H3;1H3,(H,2,3,4)/q+1;/p-1
2.1.3 InChI Key
OSZNNLWOYWAHSS-UHFFFAOYSA-M
2.1.4 Canonical SMILES
CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C.COS(=O)(=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
98IMH7M386
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bromide, Neostigmine

2. Methylsulfate, Neostigmine

3. Neostigmine

4. Neostigmine Bromide

5. Polstigmine

6. Proserine

7. Prostigmin

8. Prostigmine

9. Prozerin

10. Synstigmin

11. Syntostigmine

2.3.2 Depositor-Supplied Synonyms

1. Neostigmine Methyl Sulfate

2. 51-60-5

3. Syntostigmin

4. Normastigmin

5. Hodostin

6. Neostigmine Methylsulphate

7. Neostigmine Metilsulfate

8. Neostigmine (methyl Sulfate)

9. Neostigmeth

10. Polstigmine

11. Synstigmine

12. 3-[[(dimethylamino)carbonyl]oxy]-n,n,n-trimethylbenzenaminium Methyl Sulfate

13. Neostigmine Methosulfate

14. Neostigmine Monomethyl Sulfate

15. Eustigmin Methyl Sulfate

16. Proserine Methyl Sulfate

17. Stigmanol Methyl Sulfate

18. Stigmosan Methyl Sulfate

19. Neoeserine Methyl Sulfate

20. Syntostigmin (injection)

21. Leostigmine Methyl Sulfate

22. Kirkstigmine Methyl Sulfate

23. Philostigmin Methyl Sulfate

24. Syntostigmin Methyl Sulfate

25. Vagostigmine Methyl Sulfate

26. Prostigmin

27. Syntostigmine Methyl Sulfate

28. Synthostigmine Methyl Sulfate

29. Intrastigmina

30. Ar-32

31. Sb-23

32. 3-((dimethylcarbamoyl)oxy)-n,n,n-trimethylbenzenaminium Methyl Sulfate

33. Tl-1394

34. (m-hydroxyphenyl)trimethylammonium Methyl Sulfate Dimethylcarbamate

35. Nsc-93753

36. 51-60-5 (methylsulfate)

37. Mls000028383

38. Chebi:7516

39. Chembl211471

40. [3-(dimethylcarbamoxy)phenyl]trimethylammonium Methyl Sulfate

41. [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium;methyl Sulfate

42. 98imh7m386

43. (3-hydroxyphenyl)trimethylammonium Methyl Sulfate Dimethylcarbamic Ester

44. Juvastigmin

45. Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-, Methyl Sulfate

46. (3-(dimethylcarbamoxy)phenyl)trimethylammonium Methyl Sulfate

47. Smr000058592

48. Prostigmin (tn)

49. (3-(dimethylcarbamoyl)oxyphenyl)trimethylammonium Methyl Sulfate

50. Syntostigmin (van)

51. Eustigmin Methylsulfate

52. Proserinum

53. Bloxiverz

54. 3-(dimethylcarbamoyloxy)-n,n,n-trimethylbenzenaminium Methyl Sulfate

55. Neostigmine Monomethylsulfate

56. Neostigminmetilsulfat

57. Ccris 3274

58. Gd 65

59. Einecs 200-109-5

60. Nsc 93753

61. Kirkstigmine

62. Proserin

63. [3-(dimethylcarbamoyl)oxyphenyl]trimethylammonium Methyl Sulfate

64. Unii-98imh7m386

65. Bloxiverz (tn)

66. Neostigmine Methylsulfate [usp:jan]

67. Mfcd00011796

68. Neostigmini Metilsulfas

69. Neostigminemethylsulfate

70. 3-(dimethylcarbamoxy)phenyl Trimethylammonium Methyl Sulfate

71. Opera_id_536

72. Prostigmin Methyl Sulfate

73. Ammonium, (3-(dimethylcarbamoyloxy)phenyl)trimethyl-, Methylsulfate

74. Dimethylcarbamic Ester Of 3-oxyphenyltrimethylammonium Methylsulfate

75. Prostigmine Methyl Sulfate

76. Ammonium, (m-hydroxyphenyl)trimethyl-, Methyl Sulfate, Dimethylcarbamate

77. Carbamic Acid, N,n-dimethyl-, 3-dimethylaminophenyl Ester, Methosulfate

78. Neostigmine Methyl Sulphate

79. Carbamic Acid, N,n-dimethyl-, 3-(trimethylammonio)phenyl Ester, Methylsulfate

80. Carbamic Acid, Dimethyl-, Ester With (m-hydroxyphenyl)trimethylammonium Methyl Sulfate

81. Schembl41903

82. Mls001148660

83. Mls001333720

84. Hms500j20

85. Dtxsid40199003

86. Hms2234e04

87. Hms3371e13

88. Act05636

89. Bcp11922

90. Hy-b1206

91. Nsc93753

92. 3-[(dimethylcarbamoyl)oxy]-n,n,n-trimethylanilinium Methyl Sulfate

93. Akos015856682

94. Neostigmine Methylsulfate (jp17/usp)

95. Ac-6847

96. Ccg-213722

97. Cs-4698

98. Neostigmine Methyl Sulfate [mi]

99. Neostigmine Methylsulfate [jan]

100. Neostigmine Metilsulfate [mart.]

101. Neostigmine Methylsulfate [vandf]

102. Neostigmine Metilsulfate [who-dd]

103. Neostigmine Metilsulfate [who-ip]

104. As-15291

105. Neostigmine Methylsulfate [usp-rs]

106. Ammonium, Methyl Sulfate, Dimethylcarbamate

107. Db-051998

108. Benzenaminium,n,n-trimethyl-, Methyl Sulfate

109. Ft-0603223

110. N0447

111. Neostigmine Methylsulfate [green Book]

112. Neostigmini Metilsulfas [who-ip Latin]

113. C08200

114. C75419

115. D00998

116. Neostigmine Methylsulfate [orange Book]

117. Neostigmine Methylsulfate [usp Impurity]

118. Neostigmine Metilsulfate [ep Monograph]

119. Wln: 1n1&vor Ck1&1&1 &q &osw1

120. Neostigmine Methylsulfate [usp Monograph]

121. A828681

122. Q27107519

123. (3-(dimethylcarbamoyloxy)phenyl)trimethyl-ammoniumethylsulfate

124. (3-dimethylcarbamoyloxyphenyl)trimethylammonium Methyl Sulfate

125. (3-hydroxyphenyl)trimethylammonium Methyl Sulfate Dimethylcarbamate

126. [3-(dimethylcarbamoyloxy)phenyl]-trimethyl-azanium; Methyl Sulfate

127. 3-[[(dimethylamino)carbonyl]oxy]-n,n,n-trimethylbenzaminium Bromide

128. Dimethylcarbamic Ester Of 3-oxyphenyltrimethylammonium Methylsulfato

129. (m-hydroxyphenyl)trimethylammonium Methyl Sulphate Dimethylcarbamate

130. [3-[dimethylamino(oxo)methoxy]phenyl]-trimethylammonium; Methyl Sulfate

131. Carbamic Acid, Ester With (m-hydroxyphenyl)trimethylammonium Methyl Sulfate

132. Carbamic Acid,n-dimethyl-, 3-(trimethylammonio)phenyl Ester, Methyl Sulfate

133. Neostigmine Methyl Sulfate, European Pharmacopoeia (ep) Reference Standard

134. Benzenaminium, 3-(((dimethylamino)carbonyl)oxy)-n,n,n-trimethyl-, Methyl Sulphate

135. Neostigmine Methyl Sulfate, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 334.39 g/mol
Molecular Formula C13H22N2O6S
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass334.11985760 g/mol
Monoisotopic Mass334.11985760 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count22
Formal Charge0
Complexity337
Isotope Atom Count0
Defined Atom Stereocenter Count0
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 2  
Drug NameBloxiverz
PubMed HealthNeostigmine
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nondepolarizing Muscle Relaxant Antagonist
Drug LabelNeostigmine methylsulfate, a cholinesterase inhibitor, is (m-hydroxyphenyl) trimethylammonium methylsulfate dimethylcarbamate. The structural formula is:Neostigmine methylsulfate is a white crystalline powder and is very soluble in water and soluble...
Active IngredientNeostigmine methylsulfate
Dosage FormSolution
RouteIntravenous
Strength10mg/10ml (1mg/ml); 5mg/10ml (0.5mg/ml)
Market StatusPrescription
CompanyEclat Pharms

2 of 2  
Drug NameBloxiverz
PubMed HealthNeostigmine
Drug ClassesCentral Nervous System Agent, Immunological Agent, Nondepolarizing Muscle Relaxant Antagonist
Drug LabelNeostigmine methylsulfate, a cholinesterase inhibitor, is (m-hydroxyphenyl) trimethylammonium methylsulfate dimethylcarbamate. The structural formula is:Neostigmine methylsulfate is a white crystalline powder and is very soluble in water and soluble...
Active IngredientNeostigmine methylsulfate
Dosage FormSolution
RouteIntravenous
Strength10mg/10ml (1mg/ml); 5mg/10ml (0.5mg/ml)
Market StatusPrescription
CompanyEclat Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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]