5940. Methacholine Chloride

Nomenclature

CAS number: 62-51-1
2-(Acetyloxy)-N,N,N-trimethyl-1-propanaminium chloride; acetyl-β-methylcholine chloride; O-acetyl-β-methylcholine chloride; (2-hydroxypropyl)trimethylammonium chloride acetate; (2-acetoxypropyl)trimethylammonium chloride; trimethyl-β-acetoxypropylammonium chloride; Amechol (Moorsfields); Provocholine (Roche).
C8H18ClNO2; mol wt 195.69.
C 49.10%, H 9.27%, Cl 18.12%, N 7.16%, O 16.35%.

Description and references

Parasympathomimetic bronchoconstrictor. Prepn: R. T. Major, J. K. Cline, US 2040146 (1936 to Merck & Co.). Mechanism of ganglionic blockade in cats: R. L. Volle, J. Pharmacol. Exp. Ther. 158, 66 (1967). Clinical diagnostic efficacy in bronchial asthma: S. L. Spector, R. S. Farr, J. Allergy Clin. Immunol. 56, 308 (1975); J. G. Easton, I. Hirata, Ann. Allergy 50, 171 (1983).

Chemical structure

Properties

White, hygroscopic needles from ether, mp 172-173°. Slight odor of dead fish. Freely sol in water, alcohol, chloroform. Insol in ether. Aq solns are neutral to litmus. Should not be handled in very moist atmosphere. Bromide is less hygroscopic.
Antidote: Atropine.

Therapeutic Category

Cholinergic. Diagnostic aid (bronchial asthma).

Keywords

Cholinergic; Diagnostic Aid