Chemical Properties
Crystalline Solid
Originator
Cantil,Merrell National,US,1956
Uses
Used as an anticholinergic
Definition
ChEBI: Mepenzolate bromide is a diarylmethane.
Manufacturing Process
A mixture containing 8 g (0.06 mol) of N-methyl-3-chloro-piperidine and 13.6 g (0.06 mol) of benzilic acid in 50 cc of anhydrous isopropyl alcohol was refluxed for 3 days; the isopropyl alcohol was removed by distillation in vacuo, the residue treated with dilute aqueous hydrochloric acid and the aqueous acid mixture extracted repeatedly with ether. The aqueous phase was separated, made strongly alkaline with 20% aqueous sodium hydroxide and extracted with ether. The ether extracts were dried with potassium carbonate and distilled; the product was collected at 175° to 176°C (0.03 mm), yield 11.5 g (59 %).The ester base thus prepared was then dissolved in 75 cc of isopropyl alcohol and 3.4 g (0.037 mol) methyl bromide added. The reaction mixture was allowed to stand at 30°C for 2 days and the product isolated by filtration, yield, 13 g (87%), MP 228° to 229°C dec.
Therapeutic Function
Spasmolytic
General Description
Mepenzolate bromide, 3-hydroxy-1,1-dimethylpiperidinium bromide benzilate (Cantil),has an activity about one half that of atropine in reducingACh-induced spasms of the guinea pig ileum. The selectiveaction on colonic hypermotility is said to relieve pain, cramps,and bloating and to help curb diarrhea.
Pharmacology
Mepenzolate inhibits muscarinic action of acetylcholine on postganglionic parasympathetic effector regions. It is used in place of other drugs for treating stomach ulcers and
inflammation of the intestine. Synonyms of this drug are cantil and eftoron.
Synthesis
Mepenzolate, 3-[(hydroxydiphenylacetyl)oxy]-1,1-dimethyl piperidinium
bromide (14.1.13), is synthesized by esterification of benzilic acid with 1-methyl-3-
chloropiperidine and subsequent reaction of the resulting ester (14.1.12) with methyl
bromide [14,15].
