Carbachol

Title: Carbachol
CAS Registry Number: 51-83-2
CAS Name: 2-[(Aminocarbonyl)oxy]-N,N,N-trimethylethanaminium chloride
Additional Names: (2-hydroxyethyl)trimethyl ammonium chloride carbamate; choline chloride carbamate; carbamylcholine chloride; carbocholine
Trademarks: Doryl (Merck KGaA); Isopto Carbachol (Alcon); Jestryl (Ankerpharm); Miostat (Alcon)
Molecular Formula: C6H15ClN2O2
Molecular Weight: 182.65
Percent Composition: C 39.45%, H 8.28%, Cl 19.41%, N 15.34%, O 17.52%
Literature References: Parasympathomimetic. Prepn: O. Dalmer, C. Diehl, DE 539329 (1930 to E. Merck); eidem, US 1894162 (1933); Kreitmair, Arch. Exp. Pathol. Pharmakol. 164, 346 (1932); R. D. Haworth et al., J. Chem. Soc. 1947, 176. Toxicity: Molitor, J. Pharmacol. Exp. Ther. 58, 337 (1936). Evaluation in bronchoprovocation test for asthma: G. Rosati et al., Eur. J. Respir. Dis. 64, Suppl. 128, 417 (1983). Clinical effect on post-surgical intraocular pressure: R. S. Ruiz et al., Am. J. Ophthalmol. 107, 7 (1989).
Properties: Prismatic crystals from alcohol-ether, mp 207° (Haworth); also reported as mp 204-205° (Kreitmair). Hygroscopic. Odorless or slight amine-like odor. One gram dissolves in 1 ml water, 50 ml alcohol. Practically insol in chloroform, ether. LD50 in mice (mg/kg): 15 orally, 0.3 i.v. (Molitor).
Melting point: mp 207° (Haworth); mp 204-205° (Kreitmair)
Toxicity data: LD50 in mice (mg/kg): 15 orally, 0.3 i.v. (Molitor)
Therap-Cat: Cholinergic; miotic.
Therap-Cat-Vet: Cholinergic; miotic.
Keywords: Cholinergic; Miotic.
Carbacrylic Resins Carbadox Carbamazepine Carbamide Peroxide Carbamyl Chloride

Carbachol
Carbachol chloride.svg
Systematic (IUPAC) name
2-[(Aminocarbonyl)oxy]-N,N,N-trimethylethanaminium chloride
Clinical data
Trade names Miostat
AHFS/Drugs.com monograph
Pregnancy cat. C (US)
Legal status Prescription only
Routes Oral-Tablet, Injectable-solution, Topical-eye drops
Pharmacokinetic data
Bioavailability low
Metabolism  ?
Half-life  ?
Excretion  ?
Identifiers
CAS number 51-83-2 YesY
ATC code N07AB01 S01EB02 QA03AB92
PubChem CID 5831
IUPHAR ligand 298
DrugBank DB00411
ChemSpider 5626 YesY
UNII 8Y164V895Y YesY
KEGG D00524 YesY
ChEBI CHEBI:3385 YesY
ChEMBL CHEMBL14 YesY
Chemical data
Formula C6H15ClN2O2 
Mol. mass 182.696 g/mol
 YesY (what is this?)  (verify)

Carbachol (Carbastat, Carboptic, Isopto Carbachol, Miostat), also known as carbamylcholine, is a cholinomimetic drug that binds and activates the acetylcholine receptor. Thus it is classified as a cholinergic agonist. It is primarily used for various ophthalmic purposes, such as for treating glaucoma, or for use during ophthalmic surgery. It is generally administered as an ophthalmic solution (i.e. eyedrops).