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Studies on the metabolism of mitragynine, the main alkaloid of the herbal drug Kratom, in rat and human urine using liquid chromatography‐linear ion trap mass spectrometry
Author(s) -
Philipp Anika A.,
Wissenbach Dirk K.,
Zoerntlein Siegfried W.,
Klein Oliver N.,
Kanogsunthornrat Jidapha,
Maurer Hans H.
Publication year - 2009
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.1607
Subject(s) - chemistry , chromatography , alkaloid , urine , demethylation , designer drug , mass spectrometry , indole alkaloid , metabolic pathway , metabolism , organic chemistry , drug , biochemistry , pharmacology , medicine , gene expression , dna methylation , gene
Mitragynine (MG) is an indole alkaloid of the Thai medicinal plant Mitragyna speciosa (Kratom in Thai) and reported to have opioid agonistic properties. Because of its stimulant and euphoric effects, Kratom is used as a herbal drug of abuse. The aim of the presented study is to identify the phase I and II metabolites of MG in rat and human urine after solid‐phase extraction (SPE) using liquid chromatography‐linear ion trap mass spectrometry providing detailed structure information in the MS n mode particularly with high resolution. The seven identified phase I metabolites indicated that MG was metabolized by hydrolysis of the methylester in position 16, O ‐demethylation of the 9‐methoxy group and of the 17‐methoxy group, followed, via the intermediate aldehydes, by oxidation to carboxylic acids or reduction to alcohols and combinations of some steps. In rats, four metabolites were additionally conjugated to glucuronides and one to sulfate, but in humans, three metabolites to glucuronides and three to sulfates. Copyright © 2009 John Wiley & Sons, Ltd.