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Substance Name: Bethanechol chloride [USP:BAN:JAN]
RN: 590-63-6
UNII: H4QBZ2LO84
InChIKey: XXRMYXBSBOVVBH-UHFFFAOYSA-N

Note

  • A slowly hydrolyzed 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, cardiac rate changes, and bronchial spasms.

Molecular Formulas

  • C7-H17-Cl-N2-O2
  • C7-H17-N2-O2.Cl

Molecular Weight

  • 196.6763
 

Classification Codes

  • Cholinergic
  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Bethanechol chloride [USP:BAN:JAN]

MeSH Heading

  • Bethanechol

Synonyms

  • (+-)-(2-Hydroxypropyl)trimethylammonium chloride carbamate
  • (2-Hydroxypropyl)trimethylammonium chloride carbamate
  • 1-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-, chloride
  • 1-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-, chloride, (+-)-
  • 2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propanaminium chloride
  • 2-Carbamoyloxypropyltrimethylammonium chloride
  • Besacholine
  • beta-Methyl carbachol chloride
  • beta-Methylcholine chloride urethan
  • Bethaine choline chloride
  • Bethanechol chloride
  • BTC
  • Carbaminoyl, beta-methylcholine chloride
  • Carbamylmethylcholine chloride
  • Duvoid
  • EINECS 209-686-8
  • Mechotane
  • Mechothane
  • Mecothane
  • Mictone
  • Mictrol
  • Muscaran
  • Myocholine
  • Myotonachol
  • Myotonine
  • NSC 30783
  • Trimethyl(2-carbamoyloxypropyl)ammonium chloride
  • UNII-H4QBZ2LO84
  • Urecholine
  • Urecholine chloride
  • Uro-Carb

Systematic Names

  • (2-Hydroxypropyl)trimethylammonium chloride carbamate
  • 1-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-, chloride
  • 1-Propanaminium, 2-((aminocarbonyl)oxy)-N,N,N-trimethyl-, chloride (1:1)
  • 2-Carbamoyloxypropyltrimethylammonium chloride
  • Ammonium, (2-hydroxypropyl)trimethyl-, chloride, carbamate

Registry Numbers

CAS Registry Number

  • 590-63-6

FDA UNII

  • H4QBZ2LO84

Other Registry Number

  • 21293-39-0

Related Registry Number

  • 674-38-4 (Parent)

System Generated Number

  • 0000590636

Molecular Formulas

Molecular Formulas

  • C7-H17-Cl-N2-O2
  • C7-H17-N2-O2.Cl

Molecular Formula Fragments

  • C7-H17-N2-O2
  • Cl
  • COMPONENT

Structure Descriptors

InChI

1S/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H

InChIKey

XXRMYXBSBOVVBH-UHFFFAOYSA-N

Smiles

C([N+](C)(C)C)[C@@H](OC(N)=O)C.[ClH-]

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 13mg/kg (13mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Archives Internationales de Pharmacodynamie et de Therapie. Vol. 106, Pg. 245, 1956.
human TDLo subcutaneous 130mg/kg (130mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 130, 1969.
man TDLo subcutaneous 1071ug/kg/3D- (1.071mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Archives of Dermatology. Vol. 95, Pg. 499, 1967.
mouse LD50 intramuscular 192mg/kg (192mg/kg)   Drugs in Japan Vol. 6, Pg. 139, 1982.
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 intravenous 10mg/kg (10mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
mouse LD50 oral 250mg/kg (250mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
mouse LD50 subcutaneous 120mg/kg (120mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 intramuscular 220mg/kg (220mg/kg)   Drugs in Japan Vol. 6, Pg. 139, 1982.
rat LD50 intravenous 21mg/kg (21mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 oral 1500mg/kg (1500mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.
rat LD50 subcutaneous 175mg/kg (175mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 58, Pg. 337, 1936.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -3.370 (none)   EST
Water Solubility 6.25E+05 mg/L   EXP
Atmospheric OH Rate Constant 2.88E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.