ENANTIOMER ANALYSIS OF E-10-HYDROXYAMITRIPTYLINE AND Z-10-HYDROXYAMITRIPTYLINE IN HUMAN URINE

E- and Z-10-hydroxyamitriptyline (E- and Z-10-OH-AT) are racemic alcoholic metabolites of the antidepressant amitriptyline. Their enantiomers were separated by high-performance liquid chromatography as diastereomeric derivatives using R-(+)-α-methoxy-α-trifluoromethylphenylacetyl chloride (Mosher's reagent). Although E-10-hydroxyamitriptyline excreted in patient urine in free form or as the O-glucuronide consisted primarily of the (-)-enantiomer, the N-glucuronide contained similar amounts of the two enantiomers. Z-10-OH-AT was analysed in one patient and an excess of the (+)-isomer was found in the unconjugated, total conjugated and N-glucuronidated metabolite. The specific optical rotation of (-)-E-10-OH-AT was determined. © 1990.