Basic information
- CAS
590-63-6- Standard SMILES
CC(C[N+](C)(C)C)OC(N)=O.[Cl-]- InChIKey
XXRMYXBSBOVVBH-UHFFFAOYSA-N- Molecular formula
- C7H17ClN2O2
- Average molar mass
- 196.67 g/mol
- Monoisotopic mass
- 196.0978555
Overview
Bethanechol chloride is the chloride salt of bethanechol. A slowly hydrolysed muscarinic agonist with no nicotinic effects, it is used to increase smooth muscle tone, as in the gastrointestinal tract following abdominal surgery, treatment of gastro-oesophageal reflux disease, and as an alternative to catheterisation in the treatment of non-obstructive urinary retention. It has a role as a muscarinic agonist. It is a carbamate ester, a chloride salt and a quaternary ammonium salt. It contains a bethanechol.
Names & identifiers
- Preferred name
- Bethanechol Chloride
- IUPAC
- 2-carbamoyloxypropyl(trimethyl)azanium chloride
- English name
- Bethanechol
- Molecular formula
- C7H17ClN2O2
- Molecular weight
- 196.68
Names & synonyms
Bethanechol chloride590-63-6Myotonachol2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium chlorideDTXSID2022676Trimethyl(2-carbamoyloxypropyl)ammonium chloride(2-Hydroxypropyl)trimethylammonium chloride carbamateH4QBZ2LO84NSC-307832-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propanaminium chlorideCHEBI:3085DTXCID902676
Show more names
BetanecholBthanechol chlorideMictoneUro-CarbMechotaneMecothaneNSC 30783-β-methyL
NSC30783Chloride, BethanecholRefChem:54535(2RS)-2-Carbamoyloxy-N,N,N-trimethylpropylaminium chlorideUrecholineDuvoidMechothaneMictrol
Database identifiers
- CAS
590-63-6- PubChem CID
- 11548
- DTXSID
DTXSID2022676
Properties
Computed structural properties
- Topological polar surface area
- 52.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 140
Experimental & physicochemical properties
Solubility>29.5 [ug/mL] (The mean of the results at pH 7.4)
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section133 Ų [M]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 187 · 187-190°C
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 1.7 g/mL stable for several days at 4°C.
- form
- crystalline
- color
- white
- Water Solubility
- 2 O: · H2O: 1.7g/mL (stable for several days at 4°C.)ethanol: 80mg/mL (stable for several days at 4°C.)
- Merck
- 14 · 14,1185
- InChI
- InChI=1S/C7H16N2O2.ClH/c1-6(11-7(8)10)5-9(2,3)4;/h6H,5H2,1-4H3,(H-,8,10);1H
- InChIKey
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
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. (L1712)
Exposure RoutesOral
Toxicity Summary
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.
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
BETHANECHOL CHLORIDE
Cholinergic Muscarinic Agonists [MoA]; Cholinergic Muscarinic Agonist [EPC]
MeSH Pharmacological Classification
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.
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.
Uses & manufacturing
UsesFor the treatment of acute postoperative and postpartum nonobstructive (functional) urinary retention and for neurogenic atony of the urinary bladder with retention.
General Manufacturing Information1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride (1:1): ACTIVE
Applications
DescriptionBethanechol is an agonist of muscarinic acetylcholine receptors with IC50 values of 1,837, 25, 631, 317, and 393 μM for M1-5, respectively, in a radioligand binding assay using CHO cells expressing the human receptors. It inhibits M2-mediated increases in cyclic AMP induced by isoproterenol in isolated guinea pig small intestine (IC50 = 127 μM). Bethanechol increases basal tone of isolated porcine intravesical ureter (EC50 = 4.27 μM). It also induces fluid secretion in the ileum, duodenum, and jejunum of anesthetized rats when administered at a dose of 60 μg/kg. Formulations containing bethanechol have been used to increase urination and improve smooth muscle tone in the gastrointestinal tract.
Related reactions
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Compound notes
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