Bethanechol Chloride

Title: Bethanechol Chloride
CAS Registry Number: 590-63-6
CAS Name: 2-[(Aminocarbonyl)oxy]-N,N,N-trimethyl-1-propanaminium chloride
Additional Names: (2-hydroxypropyl)trimethylammonium chloride carbamate; 2-carbamoyloxypropyltrimethylammonium chloride; carbamylmethylcholine chloride; b-methylcholine chloride urethan
Trademarks: Duvoid (Shire); Myocholine (Glenwood); Myotonine (Glenwood); Urecholine (Merck & Co.)
Molecular Formula: C7H17ClN2O2
Molecular Weight: 196.68
Percent Composition: C 42.75%, H 8.71%, Cl 18.03%, N 14.24%, O 16.27%
Literature References: Prepn: Dalmer, Diehl, US 1894162 (1933); Major, Bonnett, US 2322375 (1943 to Merck & Co.). 1H-NMR determn in tablets: G. M. Hanna, C. A. Lau-Cam, J. Assoc. Off. Anal. Chem. 70, 557 (1987). Clinical trial in postoperative urinary retention: L. Gottesman et al., Dis. Colon Rectum 32, 867 (1989).
Properties: Hygroscopic crystals, slight amine odor, dec 218-219°. One gram dissolves in 0.6 ml of water, in 12.5 ml of 95% alc. pH of an 0.5% aq soln 5.5-6.0. Aq solns may be sterilized by autoclaving at 120° for 20 minutes.
Therap-Cat: Cholinergic; in treatment of urinary retention.
Therap-Cat-Vet: Cholinergic.
Keywords: Cholinergic.
Bethanidine Betonicine Betoxycaine Betulin Betulinic Acid

Bethanechol
Systematic (IUPAC) name
2-(Carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
Clinical data
Trade names Urecholine
AHFS/Drugs.com monograph
MedlinePlus a682849
Pregnancy cat. C (US)
Legal status  ?
Routes Oral, subcutaneous
Identifiers
CAS number 674-38-4 YesY
ATC code N07AB02
PubChem CID 2370
IUPHAR ligand 297
DrugBank DB01019
ChemSpider 2280 YesY
UNII 004F72P8F4 YesY
KEGG C06850 YesY
ChEBI CHEBI:3084 YesY
ChEMBL CHEMBL1482 YesY
Synonyms 2-[(aminocarbonyl)oxy]- N,N,N-trimethyl- 1-propanaminium
Chemical data
Formula C7H17N2O2 
Mol. mass 161.221 g/mol
 YesY (what is this?)  (verify)

Bethanechol is a parasympathomimetic choline carbamate that selectively stimulates muscarinic receptors without any effect on nicotinic receptors. Unlike acetylcholine, bethanechol is not hydrolyzed by cholinesterase and will therefore have a long duration of action. Bethanechol is sold under the brand names Duvoid (Roberts), Myotonachol (Glenwood), Urecholine (Merck Frosst) and Urocarb (Hamilton).