Bethanechol

Bethanechol Basic information
Product Name:Bethanechol
Synonyms:(2-hydroxypropyl)trimethylammoniumchloridecarbamate;2-((aminocarbonyl)oxy)-n,n,n-trimethyl-1-propanaminiuchloride;2-[(aminocarbonyl)oxy]-n,n,n-trimethyl-1-propanaminiuchloride;ammonium,(2-hydroxypropyl)trimethyl-,chloride,carbamate;beta-methylcholinechlorideurethan;bethainecholinechloride;carbaminoyl,beta-methylcholinechloride;carbamyl-b-methylcholinechloride*crystalline
CAS:590-63-6
MF:C7H17ClN2O2
MW:196.68
EINECS:209-686-8
Product Categories:Coumarins ,Pyrans;Inhibitors;DUVOID;Acetylcholine receptor;Aliphatics;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;590-63-6
Mol File:590-63-6.mol
Bethanechol Structure
Bethanechol Chemical Properties
Melting point 187-190°C
storage temp. Inert atmosphere,2-8°C
solubility H2O: 1.7 g/mL stable for several days at 4°C.
form crystalline
color white
Merck 14,1185
CAS DataBase Reference590-63-6(CAS DataBase Reference)
EPA Substance Registry System1-Propanaminium, 2-[(aminocarbonyl)oxy]-N,N,N-trimethyl-, chloride (590-63-6)
Safety Information
Hazard Codes Xn
Risk Statements 22
Safety Statements 36
WGK Germany 3
RTECS BR5425000
TSCA Yes
HS Code 2924190002
MSDS Information
ProviderLanguage
SigmaAldrich English
Bethanechol Usage And Synthesis
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.
Chemical PropertiesWhite Solid
OriginatorUrecholine CI,MSD,US,1949
UsesTherapeutic action of Betanechol is based on this action, and it is used for treating postoperational non-obstructive retention of urine and neurogenic bladder atony. Earlier, it was used for treating gastrointestinal illnesses and Alzheimer’s disease.
UsesA selective muscarinic receptor stimulant, used to treat cerebral palsy.
Usescholinergic
DefinitionChEBI: 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.
Manufacturing ProcessAbout 3 grams of β-methylcholine chloride are stirred at room temperature with an excess of phosgene dissolved in 50 grams of chloroform, for about 2 hours. Excess phosgene and hydrochloric acid are removed by distillation under vacuo. Additional chloroform is added to the syrup and the mixture is poured into excess ammonia dissolved in chloroform and cooled in solid carbon dioxide-acetone. The solid is filtered and extracted with hot absolute alcohol. The solid in the alcohol is precipitated with ether, filtered, and recrystallized from isopropanol. The carbaminoyl-β-methylcholine chloride obtained has a melting point of about 220°C.
Brand nameDuvoid (WellSpring); Myotonachol (Glenwood); Urecholine (Odyssey).
Therapeutic FunctionCholinergic
General DescriptionBethanechol, β-methylcholinechloride carbamate, (2-hydroxypropyl)trimethylammoniumchloride carbamate, carbamylmethylcholinechloride (Urecholine), is nonspecific in its action on muscarinicreceptor subtypes but appears to be more effective ateliciting pharmacological action of M3 receptors. It haspharmacological properties similar to those of methacholine.Both are esters of β-methylcholine and have feeblenicotinic activity. Bethanechol is inactivated more slowlyby AChE in vivo than is methacholine. It is a carbamyl esterand is expected to have stability in aqueous solutions similarto that of carbachol.
HazardHeadache, flushing, gastrointestinal distress, diarrhea, hypotension, excessive salivation, sweating, hypersensitivity.
Mechanism of actionBentanechol is a drug, which has structurally unique qualities of both methacholine and carbachol, i.e. it contains both β-methyl and carbamate functional groups, and quite logically exhibits pharmacological properties of both the drugs. It is resistant to hydrolysis by cholinesterases and has a very minor effect on nicotinic receptors of the autonomic ganglia and neuromuscular junctions. Betanechol has more of a selective action on muscarinic receptors of the gastrointestinal tract and the bladder than do other cholinic esters.
Clinical UseThe main use of bethanechol chloride is in the relief ofurinary retention and abdominal distention after surgery.The drug is used orally and by subcutaneous injection. Itmust never be administered by intramuscular or intravenousinjection because of the danger from cholinergic overstimulationand loss of selective action. Proper administration ofthe drug is associated with low toxicity and no serious sideeffects. Bethanechol chloride should be used with caution inasthmatic patients; when used for glaucoma, it producesfrontal headaches from the constriction of the sphinctermuscle in the eye and from ciliary muscle spasms. Its durationof action is 1 hour.
SynthesisBetanechol, 2-carbamoyloxy-1-(N,N,N-trimethyl)propyl ammonium chloride (13.1.8), is made by either the subsequent reaction of 1-(N,N,N-trimethylammonium) propan-2-ol with phosgene, followed by ammonia, or by a completely analogous synthesis of carbachol by the reaction of 1-chloro-2-propanol with phosgene followed by consequent reactions with ammonia, and then with trimethylamine, giving betanechol (13.1.8) [14,15].

Synthesis_590-63-6

Veterinary Drugs and TreatmentsIn veterinary medicine, bethanechol is used primarily to stimulate bladder contractions in small animals. It also can be used as an esophageal or general GI stimulant, although metoclopramide and/ or neostigmine have largely supplanted it for these uses.
Bethanechol Preparation Products And Raw materials
Raw materialsAmmonia-->PHOSGENE
Hemin BETHANECHOL Moclobemide ALUMINUM CLOFIBRATE Acetylcholine (2-hydroxypropyl)trimethylammonium Bethanechol Compounds Bethanechol-d6 Ferric chloride Clofibrate P-AMINOBENZAMIDE GLUTAMIC ACID L-ACYLASE Bethanechol Bethanechol-d6 Chloride Potassium chloride Acetylcholine chloride SUCCINYL CHLORIDE 2-​[[(2-​ethylphenyl)​(2-​hydroxyethyl)​amino]​methyl]​-​3,​3-​difluoro-Propanenitrile

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