PROCYCLIDINE HYDROCHLORIDE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses March 30, 2020 huzefakifayet GPAT Preparation, How to prepare for gpat, MCQ, NIPER JEE Examination (Masters/Ph.D. Admission), Pharmacy Exam Questions, Quiz, Study Material Drug Inspector Medicinal Chemistry muscarinic antagonist, GPAT chemistry questions, Pharmacist MCQ for chemistry, procyclidine Allergic reactions, procyclidine antipsychotics side effects, procyclidine Blurred vision, procyclidine Constipation, procyclidine Dizziness, procyclidine Drowsiness, procyclidine Dry mouth, PROCYCLIDINE HYDROCHLORIDE, PROCYCLIDINE HYDROCHLORIDE chemical properties, PROCYCLIDINE HYDROCHLORIDE gpat questions, PROCYCLIDINE HYDROCHLORIDE gpatindia, PROCYCLIDINE HYDROCHLORIDE mechanism of action, PROCYCLIDINE HYDROCHLORIDE MELTING POINT, PROCYCLIDINE HYDROCHLORIDE MOLECULAR WEIGHT, PROCYCLIDINE HYDROCHLORIDE NUMBER OF CHIRAL CARBONS, PROCYCLIDINE HYDROCHLORIDE OCTANOL WATER COEFFICIENT, PROCYCLIDINE HYDROCHLORIDE physical properties, PROCYCLIDINE HYDROCHLORIDE RING STRUCTURE, PROCYCLIDINE HYDROCHLORIDE SAR, PROCYCLIDINE HYDROCHLORIDE side effects, PROCYCLIDINE HYDROCHLORIDE SOLUBILITY, PROCYCLIDINE HYDROCHLORIDE structure, PROCYCLIDINE HYDROCHLORIDE synthesis, PROCYCLIDINE HYDROCHLORIDE therapeutic uses, procyclidine parkinson Procyclidine hydrochloride IUPAC nomenclature 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol;hydrochloride. Classification Procyclidine is an acetylcholine antagonist. It is a muscarinic antagonist. Physiochemical Properties S. NO. PHYSICAL AND CHEMICAL PROPERTIES 1 Molecular weight 323.9 g/mol 2 Physical appearance White crystalline substance 3 Melting point 86°C. 4 Solubility Soluble in water 5 Octanol/water partition coefficient 4.2 6 Presence of ring Benzene, pyrrolidine, cyclohexane 7 Number of chiral centers 1 Mechanism of Action Procyclidine blocks the central cholinergic receptors and balances the cholinergic and dopaminergic activity in the basal ganglia. It is also having pharmacological similarities with atropine, which results in many of its effects. It also exerts an antispasmodic effect on smooth muscle, and results in the production of mydriasis and reduction in salivation.  Structure Activity Relationship Either R1 or R2 must be heterocyclic or carbocyclic. The R3 group can be hydrogen, hydroxyl, hydroxymethyl or amide. Most potent derivatives has X as an ester. X can also be either oxygen or absent completely. The N substituent can be quaternary ammonium salt or tertiary amine or both with different alkyl groups. Maximum potency obtained when the distance between the ring substituted carbons is 2 carbon units. Method of synthesis i. cyclohexyl(phenyl) methanone reacts with ethyl-2-bromoacetate and (S)-1-phenylethylamine to give (S)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid. ii. The latter compound is reacted with B2H6 to give (S)-1-cyclohexyl-1-phenylpropane-1,3-diol. iii. On reaction with triphenylphosphine, (S)-3-chloro-1-cyclohexyl-1-phenylpropan-1-ol ca be obtained. iv. Ontreating with pyrrolidine, procyclidine hydrochloride is produced.  Therapeutic Uses Procyclidine hydrochloride is used for: Treatment of Parkinson’s disease Treatment of side effects of antipsychotics Side Effects Side effects of procyclidine are: Dry mouth Dizziness Constipation Drowsiness Allergic reactions Blurred vision MCQ Q.1 Correct statements related with the Physicochemical properties of Procyclidine hydrochloride are? I. Molecular weight = 496 gm/mol II. Physical appearance: present in white crystalline substance form III. Melting point = 199.5°C IV. Solubility: soluble in water a) I, III b) I, II, IV c) II, IV d) I Q.2 Match the following of the drugs with their correct IUPAC names. i. Methacholine A. 2-(Acetyloxy)-N,N,N-trimethylpropan-1-aminium. ii. Homatropin B. (RS)-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 3-hydroxy-2-phenylpropanoate iii. Procyclidine C. (N-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 2-hydroxy-2-phenylacetate iv. Atropin D. 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-ylpropan-1-ol a) i-B, ii-A, iii-D, iv-C b) i-A, ii-C, iii-D, iv-B c) i-D, ii-C, iii-B, iv-A d) i-A, ii-B, iii-C, iv-D Q.3 Complete the following sentence related with the mechanism of action of Procyclidine hydrochloride. ‘Procyclidine ………….. the central cholinergic receptors and ………..the cholinergic and dopaminergic activity in the basal ganglia.’ a) blocks, balances b) stimulates, balances c) balances, blocks d) balances, stimulates Q.4 Correct sequence for True/false for the classification of the drug can be? Methacoline: Cholinergic antagonist Procyclidine: Muscarinic antagonist Homatropin: Cholinergic agonist Atropin: Muscarinic antagonist a) FTFT b) TTTF c) TFTF d) FFTT Q.5 Maximum potency obtained when the distance between the ring substituted carbons in procyclidine hydrochloride is? a) 1 carbon unit b) 4 carbon unit c) 2 carbon unit d) 7 carbon unit Q.6 The correct sequence for the steps for synthesis of drug Procyclidine hydrochloride from ‘cyclohexyl(phenyl) methanone’? I. Treatment with pyrrolidine II. Reaction with triphenylphosphine III. Reaction with diborane IV. Reaction with ethyl-2-bromoacetate a) I – II b) IV – III – II – I c) I – III – II – IV d) III – IV Q.7 Side effect of drug procyclidine hydrochloride? a) Allergic reactions b) Dry mouth c) Constipation d) All of the above For More Standard and Quality Question Bank you can Join Our Test Series Programme for GPAT, NIPER JEE, Pharmacist Recruitment Exam, Drug Inspector Recruitment Exams, PhD Entrance Exam for Pharmacy ANSWERS 1-c 2-b 3-a 4-a 5-c 6-b 7-d REFERENCES  Schjelderup L, Harbitz O, Groth P, Aasen AJ. Syntheses of (S)-(+)-trihexyphenidyl hydrochloride and (S)-(+)-procyclidine hydrochloride, two anticholinergics, using (S)-(−)-3-cyclohexyl-3-hydroxy-3-phenylpropanoic acid as chiral synthon. Acta Chem. Scand.. 1987 May;41:356.