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[1-(trimethylaminiumyl)propan-2-yl] carbamate chloride
Also known as: 590-63-6, Urecholine, Duvoid, Myocholine, Besacholine, Myotonachol
Molecular Formula
C7H17ClN2O2
Molecular Weight
196.67  g/mol
InChI Key
XXRMYXBSBOVVBH-UHFFFAOYSA-N
FDA UNII
H4QBZ2LO84

A slowly hydrolyzing muscarinic agonist with no nicotinic effects. Bethanechol is generally used to increase smooth muscle tone, as in the GI tract following abdominal surgery or in urinary retention in the absence of obstruction. It may cause hypotension, HEART RATE changes, and BRONCHIAL SPASM.
1 2D Structure

[1-(trimethylaminiumyl)propan-2-yl] carbamate chloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-carbamoyloxypropyl(trimethyl)azanium;chloride
2.1.2 InChI
InChI=1S/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H
2.1.3 InChI Key
XXRMYXBSBOVVBH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C[N+](C)(C)C)OC(=O)N.[Cl-]
2.2 Other Identifiers
2.2.1 UNII
H4QBZ2LO84
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bethanechol

2. Bethanecol

3. Chloride, Bethanechol

4. Duvoid

5. Hermes, Myo

6. Myo Hermes

7. Myocholine

8. Myotonachol

9. Myotonine

10. Pms Bethanechol Chloride

11. Pms-bethanechol Chloride

12. Urecholine

13. Urocarb

2.3.2 Depositor-Supplied Synonyms

1. 590-63-6

2. Urecholine

3. Duvoid

4. Myocholine

5. Besacholine

6. Myotonachol

7. Carbamyl-beta-methylcholine Chloride

8. Mechotane

9. Mechothane

10. Mecothane

11. Mictone

12. Mictrol

13. Bethanechol (chloride)

14. Uro-carb

15. Urecholine Chloride

16. Carbamylmethylcholine Chloride

17. Bethaine Choline Chloride

18. 2-carbamoyloxypropyltrimethylammonium Chloride

19. Trimethyl(2-carbamoyloxypropyl)ammonium Chloride

20. 2-(carbamoyloxy)-n,n,n-trimethylpropan-1-aminium Chloride

21. (2-hydroxypropyl)trimethylammonium Chloride Carbamate

22. 2-(carbamoyloxy)-n,n,n-trimethyl-1-propanaminium Chloride

23. Beta-methyl Carbachol Chloride

24. Nsc-30783

25. 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-1-propanaminium Chloride

26. 1-propanaminium, 2-[(aminocarbonyl)oxy]-n,n,n-trimethyl-, Chloride

27. H4qbz2lo84

28. Mls000028675

29. Chebi:3085

30. Myotonine

31. 2-carbamoyloxypropyl(trimethyl)azanium;chloride

32. Muscaran

33. Smr000058680

34. 1-propanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride

35. Dsstox_cid_2676

36. Mfcd00055224

37. (2-carbamoyloxypropyl)trimethylammonium Chloride

38. Dsstox_rid_76686

39. Dsstox_gsid_22676

40. Myotonine Chloride

41. Beta-methylcholine Chloride Urethan

42. Sr-01000000282

43. Ncgc00163217-01

44. Einecs 209-686-8

45. Nsc 30783

46. Unii-h4qbz2lo84

47. Carbaminoyl, Beta-methylcholine Chloride

48. 1-propanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride (1:1)

49. 1-propanaminium, 2-[(aminocarbonyl)oxy]-n,n,n-trimethyl-, Chloride (1:1)

50. Carbamyl-

51. A-methylcholine Chloride

52. Urecholine (tn)

53. Bethanechol Chloride [usp:ban:jan]

54. Regid855684

55. Opera_id_1125

56. Cas-590-63-6

57. Chembl1768

58. Schembl37393

59. Ammonium, Chloride, Carbamate

60. Mls001148071

61. Mls006011984

62. Spectrum1500146

63. Dtxsid2022676

64. .beta.-methyl Carbachol Chloride

65. Hms500i21

66. Hy-b0406a

67. (+-)-(2-hydroxypropyl)trimethylammonium Chloride Carbamate

68. Bethanechol Chloride [mi]

69. Carbamyl-ss-methylcholine Chloride

70. Bethanechol Chloride (jp17/usp)

71. Bethanechol Chloride [jan]

72. Hms1571g08

73. Hms1920g19

74. Hms2091m19

75. Hms2098g08

76. Hms2232d09

77. Hms3259l15

78. Hms3260n10

79. Hms3374d01

80. Hms3656g21

81. Hms3715g08

82. Hms3884h19

83. Pharmakon1600-01500146

84. Nsc30783

85. Bethanechol Chloride [vandf]

86. Tox21_112028

87. Tox21_500304

88. Ammonium, (2-hydroxypropyl)trimethyl-, Chloride, Carbamate

89. Bethanechol Chloride [mart.]

90. Ccg-38936

91. Nsc755913

92. S2455

93. .beta.-methylcholine Chloride Urethan

94. Bethanechol Chloride [usp-rs]

95. Bethanechol Chloride [who-dd]

96. 1-propanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride, (+-)-

97. Akos006230324

98. Carbamyl- Beta -methylcholine Chloride

99. Tox21_112028_1

100. Carbamyl-beta-methylcholine Chloride.cd

101. Lp00304

102. Nc00660

103. Nsc-755913

104. Ncgc00015245-10

105. Ncgc00093753-01

106. Ncgc00093753-02

107. Ncgc00093753-03

108. Ncgc00093753-04

109. Ncgc00093753-05

110. Ncgc00260989-01

111. ( Inverted Exclamation Marka)-bethanechol

112. As-13371

113. Bethanechol Chloride [orange Book]

114. Carbaminoyl, .beta.-methylcholine Chloride

115. Wln: Zvoy1&1k1&1&1 &q &g

116. Bethanechol Chloride [usp Monograph]

117. Carbamyl-b-methylcholinechloride*crystalline

118. Eu-0100304

119. Ft-0622944

120. Ft-0663092

121. Ft-0663093

122. Sw197254-3

123. En300-51035

124. C 5259

125. C08202

126. D01000

127. F20466

128. A832139

129. Sr-01000000282-2

130. Sr-01000000282-4

131. Sr-01000000282-7

132. Q27105939

133. (+/-)-(2-hydroxypropyl)trimethylammonium Chloride Carbamate

134. 2-[(aminocarbonyl)oxy]-n,n,n-trimethylpropan-1-aminium Chloride

135. 1-propanaminium, 2-((aminocarbonyl)oxy)-n,n,n-trimethyl-, Chloride, (+/-)-

136. 2-carbamoyloxypropyl(trimethyl)ammonium Chloride;2-(carbamoyloxy)-n,n,n-trimethyl-1-propanaminium Chloride

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 196.67 g/mol
Molecular Formula C7H17ClN2O2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass196.0978555 g/mol
Monoisotopic Mass196.0978555 g/mol
Topological Polar Surface Area52.3 Ų
Heavy Atom Count12
Formal Charge0
Complexity140
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
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 NameBethanechol chloride
Drug LabelBethanechol chloride, a cholinergic agent, is a synthetic ester which is structurally and pharmacologically related to acetylcholine.It is designated chemically as 2-[(aminocarbonyl)oxy]-N, N, N-trimethyl-1-propanaminium chloride. Its molecular formu...
Active IngredientBethanechol chloride
Dosage FormTablet
Routeoral; Oral
Strength5mg; 25mg; 50mg; 10mg
Market StatusPrescription
CompanyEmcure Usa; Wockhardt; Upsher Smith; Amneal Pharm; Lannett; Sun Pharm Inds; Pharmax; Impax Labs

2 of 4  
Drug NameUrecholine
PubMed HealthBethanechol
Drug ClassesCholinergic, Urinary Antispasmodic
Active IngredientBethanechol chloride
Dosage FormTablet
RouteOral
Strength25mg; 5mg; 50mg; 10mg
Market StatusPrescription
CompanyOdyssey Pharms

3 of 4  
Drug NameBethanechol chloride
Drug LabelBethanechol chloride, a cholinergic agent, is a synthetic ester which is structurally and pharmacologically related to acetylcholine.It is designated chemically as 2-[(aminocarbonyl)oxy]-N, N, N-trimethyl-1-propanaminium chloride. Its molecular formu...
Active IngredientBethanechol chloride
Dosage FormTablet
Routeoral; Oral
Strength5mg; 25mg; 50mg; 10mg
Market StatusPrescription
CompanyEmcure Usa; Wockhardt; Upsher Smith; Amneal Pharm; Lannett; Sun Pharm Inds; Pharmax; Impax Labs

4 of 4  
Drug NameUrecholine
PubMed HealthBethanechol
Drug ClassesCholinergic, Urinary Antispasmodic
Active IngredientBethanechol chloride
Dosage FormTablet
RouteOral
Strength25mg; 5mg; 50mg; 10mg
Market StatusPrescription
CompanyOdyssey Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Muscarinic Agonists

Drugs that bind to and activate muscarinic cholinergic receptors (RECEPTORS, MUSCARINIC). Muscarinic agonists are most commonly used when it is desirable to increase smooth muscle tone, especially in the GI tract, urinary bladder and the eye. They may also be used to reduce heart rate. (See all compounds classified as Muscarinic Agonists.)


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
Cholinergic Muscarinic Agonists [MoA]; Cholinergic Muscarinic Agonist [EPC]
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  • TABLET;ORAL - 10MG
  • TABLET;ORAL - 25MG
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