OXYPHENCYCLIMINE

Oxyphencyclimine is widely used for the same indications as dicyclomine and oxybutynin.

Oxyphencycliminehydrochloride, 1,4,5,6-tetrahydro-1-methyl-2-pyrimidinyl)methyl -phenylcyclohexaneglycolate monohydrochloride(Daricon, Vistrax), was introduced in 1958 and promoted asa peripheral anticholinergic–antisecretory agent, with little orno curare-like activity and little or no ganglionic blocking activity.These activities are probably absent because of the tertiarycharacter of the molecule. This activity is in contrastwith that of compounds that couple antimuscarinic actionwith ganglionic blocking action. The tertiary character of thenitrogen promotes intestinal absorption of the molecule.Perhaps the most significant activity of this compound is itsmarked ability to reduce both the volume and the acid contentof the gastric juices, a desirable action in view of the more recenthypotheses pertaining to peptic ulcer therapy. Anotherimportant feature of this compound is its low toxicity in comparisonwith many of the other available anticholinergics.Oxyphencyclimine hydrochloride is hydrolyzed in the presenceof excessive moisture and heat. It is absorbed from theGI tract and has a duration of action of up to 12 hours.

Oxyphencyclimine hydrochloride is suggested for usein peptic ulcer, pylorospasm, and functional bowel syndrome.It is contraindicated, as are other anticholinergics,in patients with prostatic hypertrophy and glaucoma.

Oxyphencylimine, the 1,4,5,6-tetrahydro-1-methyl-2-pyrimidinylmethanolic ester of |á-phenylcyclohexaneglycolic acid (14.1.37), is synthesized by the esterification of |á-phenyl-|á-cyclohexaneglycolic acid with 2-chloromethyl-1-methyl- 1,4,5,6-tetrahydropyrimidine (14.1.36) in the presence of potassium iodide. The initial 2-chloromethyl-1-methyl-1,4,5,6-tetrahydropyrimidine (14.1.36), is synthesized in turn by reacting methyl ester of iminochloracetic acid with 3-methylaminopropylamine [27¨C29].