ContaminantDB: Bethanechol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:10 UTC

Update Date

2026-05-14 16:56:00 UTC

Accession Number

CHEM002321

Identification

Common Name

Bethanechol

Class

Small Molecule

Description

Bethanechol 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(2-Hydroxypropyl)trimethylammonium carbamate	ChEBI
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium	ChEBI
2-Carbamoyloxypropyl-trimethylazanium	ChEBI
Amidopropyldimethylbetaine	ChEBI
Carbamoyl-beta-methylcholine	ChEBI
Carbamyl-beta-methylcholine	ChEBI
(2-Hydroxypropyl)trimethylammonium carbamic acid	Generator
Carbamoyl-b-methylcholine	Generator
Carbamoyl-β-methylcholine	Generator
Carbamyl-b-methylcholine	Generator
Carbamyl-β-methylcholine	Generator
Besacholine	HMDB
beta-Methyl carbachol chloride	HMDB
Bethaine choline chloride	HMDB
Bethanechol chloride	HMDB
BTC	HMDB
Carbamylmethylcholine chloride	HMDB
Chloride, bethanechol	HMDB
Organon brand OF bethanechol chloride	HMDB
PMSBethanechol chloride	HMDB
Duvoid	HMDB
Hermes, myo	HMDB
Myo hermes	HMDB
Myotonachol	HMDB
Roberts brand OF bethanechol chloride	HMDB
Glenwood brand OF bethanechol chloride	HMDB
Hamilton brand OF bethanechol chloride	HMDB
PMS-Bethanechol chloride	HMDB
Pharmascience brand OF bethanechol chloride	HMDB
Urocarb	HMDB
Bethanecol	HMDB
Myocholine	HMDB
Myotonine	HMDB
PMS Bethanechol chloride	HMDB
Urecholine	HMDB

Chemical Formula

C₇H₁₇N₂O₂

Average Molecular Mass

161.222 g/mol

Monoisotopic Mass

161.129 g/mol

CAS Registry Number

674-38-4

IUPAC Name

1-(trimethylazaniumyl)propan-2-yl carbamate

Traditional Name

bethanechol

SMILES

CC(C[N+](C)(C)C)OC(N)=O

InChI Identifier

InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1

InChI Key

NZUPCNDJBJXXRF-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium 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 Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester (CHEBI:3084 )
quaternary ammonium ion (CHEBI:3084 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

muscarinic agonist

Biological Roles

muscarinic agonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	about 220°C
Boiling Point	Not Available
Solubility	10 mg/mL (chloride salt)

Predicted Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-4.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.44 m³·mol⁻¹	ChemAxon
Polarizability	17.73 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fu-9200000000-ce89fb005ab6417b9823	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-3900000000-3dba79e269dc8a5a9906	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w2a-7900000000-5938fdfa6269132e896a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h2g-9300000000-a630235eb0d4cfee2ba0	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral

Mechanism of Toxicity

Bethanechol 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.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Atropine 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

External Links

DrugBank ID

DB01019

HMDB ID

HMDB0015154

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID