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Dumasia MC. 
“Identification of some N-hydroxylated metabolites of +/--3,4-methylenedioxymethamphetamine in horse urine by gas chromatography-mass spectrometry”. 
Xenobiotica. 2003 Oct 13;33(10):1013-25.
Abstract
1. The in vivo biotransformation of -3,4-methylenedioxymethamphetamine [-MDMA] in the thoroughbred horse was determined after oral administration. 2. Unconjugated compounds and aglycones were isolated from enzyme-hydrolysed urine by solid-phase extraction using mixed-mode cartridges. The basic isolates were derivatized trimethylsilylether, TMS and analysed by positive-ion electron ionization/gas chromatography-mass spectrometry EI+/GC-MS. MDMA and 10 Phase I metabolites containing the arylisopropylamine substructure were detected. 3. N-Hydroxy amphetamine and N-hydroxymethamphetamine were synthesized. The EI + mass spectra of their O-TMS derivatives showed characteristic &1072-cleavage ions at m/z 132 and 146, respectively, as base peaks. Based upon these data, five putative N-hydroxylated metabolites of MDMA were detected. 4. In the horse, -MDMA is metabolized by oxidative N-demethylation to form the primary amine methylenedioxyamphetamine MDA. Both MDMA and MDA are further metabolized by oxidative demethylenation cleavage and O-demethylation of the benzodioxole moiety to form the corresponding catechols, 3-O-methylation to form the guaiacols and N-oxidation of the secondary and primary amine metabolites to form the hydroxylamines. 5. Both phenolic and N-hydroxy metabolites of -MDMA undergo Phase II conjugation before excretion in urine.
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