Aromatic hydroxylation of methylenedioxybenzene (MDB) and methylenedioxymethamphetamine (MDMA) by rabbit liver microsomes

Xenobiotica; the Fate of Foreign Compounds in Biological Systems
Y KumagaiA K Cho


1. Metabolites formed during incubation of methylenedioxybenzene (MDB) and methylenedioxymethamphetamine (MDMA) with rabbit liver microsomes were examined by h.p.l.c.-electrochemical detection and g.l.c.-mass spectrometry. 2. The trifluoroacetyl derivative of metabolite M-1, obtained from MDB, had a molecular ion at m/z 234 and was identified as 3,4-methylenedioxy-6-hydroxybenzene (sesamol) by comparison with authentic material. 3. The trifluoroacetyl derivative of metabolite M-2, obtained from MDMA, exhibited a molecular ion at m/z 401. Experiments with the deuterium substituted variants of MDMA indicated that the product was hydroxylated on the aromatic ring. 4. The formation of these hydroxylated metabolites required NADPH and was inhibited by carbon monoxide, indicating the possible participation of cytochrome P-450. Phenobarbital (PB) induction caused a marked enhancement of MDP hydroxylase activity whereas MDMA hydroxylation was not affected. 5. The aromatic hydroxylation of MDB and MDMA was also observed in a reconstituted system with cytochrome P-450 isozyme IIB4.


Jan 1, 1975·Biochemical Pharmacology·C Sachs, G Jonsson
May 1, 1991·Chemical Research in Toxicology·Y KumagaiA K Cho
Oct 26, 1988·European Journal of Pharmacology·C J Schmidt, V L Taylor
Jun 1, 1969·Biochemical Pharmacology·J V Dingell, A D Bass

Related Concepts

Sesamol, ion (1+)
Carbon Monoxide
High Pressure Liquid Chromatography Procedure
Cytochrome P-450 Oxygenase
Mixed Function Oxygenases
Microsomes, Liver

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