title: Amitriptyline metabolites in human urine. Identification of phenols, dihydrodiols, glycols, and ketones.
abstract: From the urine patients being treated with amitriptyline, drug metabolites were extracted by adsorption to polystyrene. Nonconjugated compounds and aglycones liberated by enzymic hydrolysis were purified separately by repeated TLC and characterized by physicochemical and chemical methods. Besides the known E- and Z-10-hydroxy derivatives of amitriptyline (AT), nortriptyline (NT), and their primary amine analogue, two isomeric 10,11-dihydroxy compounds could be identified in each series. Metabolites with an oxo function in position 10 occurred in minor quantities. The phenols 2-hydroxy-NT and 2,11-dihydroxy-NT, as well as the 1,2-dihydrodiol derived from NT, were regularly present, while the corresponding tertiary amines as well as 3-hydroxy-AT and -NT were detected occasionally in very small amounts.
mesh_terms: D000639:Amitriptyline / Q000652:urine*; D001711:Biotransformation; D002855:Chromatography, Thin Layer; D005260:Female; D006018:Glycols / Q000378:metabolism; D006801:Humans; D007659:Ketones / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010636:Phenols / Q000378:metabolism; D012015:Reference Standards
chemical_list: D006018:Glycols; D007659:Ketones; D010636:Phenols; D000639:Amitriptyline