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    Chemistry

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    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
    Bethanechol
    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

    Bethanechol

    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]

    API Reference Price

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    [{"dataSource":"API Export","activeIngredients":"BETHANECHOL","year":"2021","qtr":"Q2","strtotime":1620412200,"product":"OTHER ORGANICS COMPOUND - BETHANECHOL CH LORIDE USP","address":"SETHNA BUILDING, 4TH FLR,55, MAHARSHI KARVE ROAD, MARINE","city":"LINES, MUMBAI ,MAHARASHTRA","supplier":"MEGAFINE PHARMA (P) LIMITED","supplierCountry":"INDIA","foreign_port":"MONTEVIDEO -","customer":"TO THE ORDER OF,","customerCountry":"URUGUAY","quantity":"2.50","actualQuantity":"2.5","unit":"KGS","unitRateFc":"3773.6","totalValueFC":"9279.4","currency":"USD","unitRateINR":271884.29999999999,"date":"08-May-2021","totalValueINR":"679710.75","totalValueInUsd":"9279.4","indian_port":"BOMBAY AIR","hs_no":"29224990","bill_no":"1655721","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"URUGAY","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"SETHNA BUILDING, 4TH FLR,55, MAHARSHI KARVE ROAD, MARINE, LINES, MUMBAI ,MAHARASHTRA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2022","qtr":"Q2","strtotime":1649788200,"product":"BETHANECHOL CHLORIDE USP","address":"D-4, MIDC, CHIKALTHANA, Contact No: 919619382911","city":"AURANGABAD","supplier":"WOCKHARDT","supplierCountry":"INDIA","foreign_port":"MONTEVIDEO -","customer":"BRANDT LABORATORIOS DEL ","customerCountry":"URUGUAY","quantity":"2.50","actualQuantity":"2.5","unit":"KGS","unitRateFc":"1100","totalValueFC":"2518.3","currency":"USD","unitRateINR":76000,"date":"13-Apr-2022","totalValueINR":"190000","totalValueInUsd":"2518.3","indian_port":"BOMBAY AIR","hs_no":"29231000","bill_no":"9687509","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"URUGAY","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"D-4, MIDC, CHIKALTHANA, Contact No: 919619382911, AURANGABAD","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2022","qtr":"Q3","strtotime":1657650600,"product":"BETHANECHOL CHLORIDE USP","address":"D-4, MIDC, CHIKALTHANA, Contact No: 919619382911","city":"AURANGABAD","supplier":"WOCKHARDT","supplierCountry":"INDIA","foreign_port":"MONTEVIDEO -","customer":"BRANDT LABORATORIOS DEL ","customerCountry":"URUGUAY","quantity":"3.50","actualQuantity":"3.5","unit":"KGS","unitRateFc":"1000","totalValueFC":"3219.5","currency":"USD","unitRateINR":73142.857142857145,"date":"13-Jul-2022","totalValueINR":"256000","totalValueInUsd":"3219.5","indian_port":"BOMBAY AIR","hs_no":"29231000","bill_no":"2787252","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"URUGAY","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"D-4, MIDC, CHIKALTHANA, Contact No: 919619382911, AURANGABAD","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q2","strtotime":1681065000,"product":"BETHANECHOL CHLORIDE USP - BATCH NO:EYS1","address":"B-1701, LOTUS CORPORATE PARK OFF W E HIGHWAY, GOREGAON E","city":"MUMBAI","supplier":"AMOLI ORGANICS","supplierCountry":"INDIA","foreign_port":"SINGAPORE","customer":"TO THE ORDER OF'","customerCountry":"SINGAPORE","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"450","totalValueFC":"22061.2","currency":"USD","unitRateINR":36160,"date":"10-Apr-2023","totalValueINR":"1808000","totalValueInUsd":"22061.2","indian_port":"BOMBAY AIR","hs_no":"29420090","bill_no":"9172264","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"SINGAPORE","selfForZScoreResived":"Pharma Grade","supplierPort":"BOMBAY AIR","supplierAddress":"B-1701, LOTUS CORPORATE PARK OFF W E HIGHWAY, GOREGAON E, MUMBAI","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2023","qtr":"Q4","strtotime":1700159400,"product":"BETHANECHOL CHLORIDE BATCH NO. 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    08-May-2021
    30-Apr-2024
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    USFDA APPLICATION NUMBER - 88440

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