Procyclidine

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia, Parkinson's disease, and idiopathic or secondary dystonia.

Procyclidine is an anticholinergic drug principally used for the treatment of drug-induced parkinsonism, akathisia and acute dystonia, Parkinson's disease, and idiopathic or secondary dystonia.

Side effects

Side effects include nausea, constipation, urinary retention, blurred vision, anxiety, cognitive impairment, confusion, dizziness, gingivitis, hallucination, memory loss, rash and vomiting.

Pharmacology

Pharmacodynamics

Procyclidine is an anticholinergic. It is specifically an antimuscarinic. The drug acts as a non-selective antagonist of the muscarinic acetylcholine M 1 , M 2 , and M 4 receptors, whereas its activities at the M 3 and M 5 receptors are reportedly unknown.

Chemistry

Synthesis

Procyclidine, 1-cyclohexyl-1-phenyl-3-pyrrolidinopropan-1-ol, is synthesized in exactly the same manner as was seen for trihexyphenidyl, except this time the linear synthesis begins with the preparation of 3-(1-pyrrolidino)propiophenone. In an interesting variation, the ketone is first reacted with phenylmagnesium bromide. Catalytic hydrogenation of the carbinol thus obtained can be stopped after the reduction of only one aromatic ring. Morton method: The Reformatsky reaction between Cyclohexyl phenyl ketone (BzCy) [712-50-5] (1) and Ethyl Bromoacetate [105-36-2] (2) gives ethyl 3-cyclohexyl-3-hydroxy-3-phenylpropanoate, PC12565684 (3). The reduction of the ester gives 1-cyclohexyl-1-phenylpropane-1,3-diol, PC13841193 (4). FGI of the primary alcohol to the Tosyl leaving group gives 3-Cyclohexyl-3-hydroxy-3-phenylpropyl 4-methylbenzenesulfonate [102473-43-8] (5). Alkylation with pyrrolidine [123-75-1] completes the synthesis of procyclidine.

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