Enantiomer analysis of E- 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-(+)-alpha-methoxy-alpha-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.
Nusser
E
E
Department of Toxicology, University of Tübingen, F.R.G.
Nill
K
K
Breyer-Pfaff
U
U
D000639:Amitriptyline / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000627:therapeutic use / Q000652:urine; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D005260:Female; D005965:Glucuronates / Q000652:urine; D006801:Humans; D015394:Molecular Structure; D013237:Stereoisomerism
D005965:Glucuronates; D000639:Amitriptyline; C033738:10-hydroxyamitriptyline