What one hand giveth the other taketh away: some unpredicted effects of enantiomers in psychopharmacology.
It is well known that many medicines are a mixture of two enantiomers, or mirror-image molecules. Two enantiomers occur when a molecule has a single chiral centre and the two mirror images, called S or L (left handed) and R or D (right handed), are usually found in equal amounts in the parent (racemic) mixture. While for many compounds used in clinical practice the active moiety is found in one of the two enantiomers with the other being seen as an unnecessary and redundant component of the racemic mixture, the difference between enantiomers can mean a difference between therapeutic and adverse effects, as well as in beneficial pharmacological effect and potency.
Nutt
David J
DJ
Neuropsychopharmacology Unit, Centre for Pharmacology and Therapeutics, Imperial College London, Hammersmith Hospital, London, UK. D.Nutt@imperial.ac.uk
Feetam
Celia L
CL
D000818:Animals; D053961:Azabicyclo Compounds / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D015283:Citalopram / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D000069582:Eszopiclone; D005473:Fluoxetine / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D001523:Mental Disorders / Q000188:drug therapy*; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology; D011619:Psychotropic Drugs / Q000009:adverse effects / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D051381:Rats; D017367:Selective Serotonin Reuptake Inhibitors / Q000009:adverse effects / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D053961:Azabicyclo Compounds; D015283:Citalopram; D000069582:Eszopiclone; D005473:Fluoxetine; D010879:Piperazines; D011619:Psychotropic Drugs; D017367:Selective Serotonin Reuptake Inhibitors; C515050:zopiclone