Bethanechol (CHEM002321)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:10 UTC
Update Date2016-11-09 01:08:44 UTC
Accession NumberCHEM002321
Identification
Common NameBethanechol
ClassSmall Molecule
DescriptionBethanechol is a synthetic ester structurally and pharmacologically related to acetylcholine. 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. [PubChem]
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Carbamate
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Muscarinic Agonist
  • Organic Compound
  • Parasympathomimetic
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2-Hydroxypropyl)trimethylammonium carbamateChEBI
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminiumChEBI
2-Carbamoyloxypropyl-trimethylazaniumChEBI
AmidopropyldimethylbetaineChEBI
Carbamoyl-beta-methylcholineChEBI
Carbamyl-beta-methylcholineChEBI
(2-Hydroxypropyl)trimethylammonium carbamic acidGenerator
Carbamoyl-b-methylcholineGenerator
Carbamoyl-β-methylcholineGenerator
Carbamyl-b-methylcholineGenerator
Carbamyl-β-methylcholineGenerator
BesacholineHMDB
beta-Methyl carbachol chlorideHMDB
Bethaine choline chlorideHMDB
Bethanechol chlorideHMDB
BTCHMDB
Carbamylmethylcholine chlorideHMDB
Chloride, bethanecholHMDB
Organon brand OF bethanechol chlorideHMDB
PMSBethanechol chlorideHMDB
DuvoidHMDB
Hermes, myoHMDB
Myo hermesHMDB
MyotonacholHMDB
Roberts brand OF bethanechol chlorideHMDB
Glenwood brand OF bethanechol chlorideHMDB
Hamilton brand OF bethanechol chlorideHMDB
PMS-Bethanechol chlorideHMDB
Pharmascience brand OF bethanechol chlorideHMDB
UrocarbHMDB
BethanecolHMDB
MyocholineHMDB
MyotonineHMDB
PMS Bethanechol chlorideHMDB
UrecholineHMDB
Chemical FormulaC7H17N2O2
Average Molecular Mass161.222 g/mol
Monoisotopic Mass161.129 g/mol
CAS Registry Number674-38-4
IUPAC Name1-(trimethylazaniumyl)propan-2-yl carbamate
Traditional Namebethanechol
SMILESCC(C[N+](C)(C)C)OC(N)=O
InChI IdentifierInChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1
InChI KeyNZUPCNDJBJXXRF-UHFFFAOYSA-O
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassQuaternary ammonium salts
Direct ParentTetraalkylammonium salts
Alternative Parents
Substituents
  • Tetraalkylammonium salt
  • Carboximidic acid derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Imine
  • Amine
  • Organic cation
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Pointabout 220°C
Boiling PointNot Available
Solubility10 mg/mL (chloride salt)
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP-2.8ALOGPS
logP-4.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)15.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area52.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.44 m³·mol⁻¹ChemAxon
Polarizability17.73 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9200000000-ce89fb005ab6417b9823Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3900000000-3dba79e269dc8a5a9906Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2a-7900000000-5938fdfa6269132e896aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h2g-9300000000-a630235eb0d4cfee2ba0Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityBethanechol directly stimulates cholinergic receptors in the parasympathetic nervous system while stimulating the ganglia to a lesser extent. Its effects are predominantly muscarinic, inducing little effect on nicotinic receptors and negligible effects on the cardiovascular system.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentAtropine Sulfate is a specific antidote. The recommended dose for adults is 0.6 mg. Repeat doses can be given every two hours, according to clinical response. The recommended dosage in infants and children up to 12 years of age is 0.01 mg/kg (to a maximum single dose of 0.4 mg) repeated every two hours as needed until the desired effect is obtained or adverse effects of atropine preclude further usage. Subcutaneous injection of atropine is preferred except in emergencies when the intravenous route may be employed. (2)
Concentrations
Not Available
DrugBank IDDB01019
HMDB IDHMDB0015154
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBethanechol
Chemspider ID2280
ChEBI ID3084
PubChem Compound ID2370
Kegg Compound IDC06850
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Major, R.T. and Bonnett, H.T.; U.S. Patent 2,322,375: June 22,1943; assigned to Merck &
Co., Inc.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17889543