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Implications of chirality and geometric isomerism in some psychoactive drugs and their metabolites
Authors:R T Coutts  G B Baker
Institution:Faculty of Pharmacy and Pharmaceutical Sciences, University of Alberta, Edmonton, Canada.
Abstract:Many drugs contain a chiral centre, or such a centre is introduced during metabolism of the drug in man and in animals. If a single chiral centre is present, the drug will normally exist as a mixture of two enantiomers, of which one may have quite different pharmacologic and/or toxic effects than the other. Chiral drugs that are used in psychiatry, and some other pharmacologically related drugs are identified, and the implications of the presence of one or two chiral centres in these drugs are discussed. Differences in pharmacologic properties of drug and metabolite enantiomers are identified and discussed. Also reviewed are the properties of some drugs used in psychiatry that both are chiral and display geometric isomerism.
Keywords:asymmetry  enantiomers  geometric isomers  (+)- (?)-isomers  D- and L-isomers  R- and S-isomers  Z- and E-isomers  drug metabolism  stereoselectivity and stereospecificity in drug action  stereoselectivity and stereospecificity in drug metabolism  psychotropic drugs  stimulants  antidepressants
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