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In vivo formation of aromatic hydroxylated metabolites of 3,4‐(methylenedioxy)methamphetamine in the rat: Identification by ion trap tandem mass spectrometric (MS/MS and MS/MS/MS) techniques
Author(s) -
Lim H. K.,
Foltz R. L.
Publication year - 1991
Publication title -
biological mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1052-9306
DOI - 10.1002/bms.1200201105
Subject(s) - methylenedioxy , chemistry , structural isomer , hydroxylation , designer drug , tandem mass spectrometry , chromatography , in vivo , metabolite , methamphetamine , mass spectrometry , mdma , stereochemistry , biochemistry , pharmacology , enzyme , organic chemistry , drug , alkoxy group , biology , alkyl , microbiology and biotechnology
Aromatic hydroxylation has been established as a pathway for the in vivo metabolism of 3,4‐(methylenedioxy)methamphetamine (MDMA) in the rat. Hydroxylation occurred at positions 2, 5 and 6 of the 3,4‐methylenedioxyphenyl ring, but is favored at the 6 position. All three regioisomers of both hydroxy‐MDMA and hydroxy‐3,4‐(methylenedioxy)amphetamine (hydroxy‐MDA) were detected in the rat liver when 20 mg kg −1 of MDMA was administered. However, 6‐hydroxy‐MDMA and 6‐hydroxy‐MDA were the only hydroxylated metabolites detected in the rat brain and plasma and no hydroxylated metabolites were detected in the urine. The hydroxylated metabolites were identified by co‐injection of synthetic reference compounds and comparison of the mass spectra of the trifluoroacetyl derivatives of the metabolites with the synthesized reference compounds. The regioisomers of both hydroxy‐MDMA and hydroxy‐MDA could not be distinguished by either single‐stage or two‐stage mass analysis. However, employment of a third stage of mass analysis produced distinctly different mass spectra for each of the three regioisomers.