Metabolism and Urinary Excretion of N-Hydroxy-3,4-methylenedioxymethamphetamine, a Recently Banned Narcotic in Japan

徹, 鎌田; 宗弘, 片木; 啓子, 中西; 桂, 財津; 典明, 志摩; 寛恵, 鎌田; 昭宏, 三木; 均, 土橋

doi:10.3408/jafst.15.15

Cited by 3 publications

(2 citation statements)

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“…The finding (ii) was in accordance with the result of the direct analysis of the N-OH-MDMA-glucuronide. The findings (iii) and (iv) were consistent with the previous works (Kamata et al, 2010;Kikura-Hanajiri et al, 2010).…”

Section: Urinary Excretion Profiles After Oral N-oh-mdma Administratisupporting

confidence: 93%

“…In vitro metabolic studies using human liver S9 fraction (Kamata et al, 2010) or human hepatocytes showed N-OH-MDMA was mainly metabolised to MDMA and 3, 4-methylenedioxyamphetamine (MDA, Figure 1C). In in vivo studies, MDMA and MDA were the main urinary metabolites of intraperitoneally administered N-OH-MDMA in rats, and only very small amounts were excreted as the unchanged form and the demethylated form N-hydroxy-3,4-MDA (N-OH-MDA, Figure 1D) (Kamata et al, 2010;Kikura-Hanajiri et al, 2010).…”

Section: Introductionmentioning

confidence: 97%

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Urinary excretion profiles ofN-hydroxy-3,4-methylenedioxymethamphetamine in rats

et al. 2011

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N-hydroxy-3,4-methylenedioxymethamphetamine (N-OH-MDMA) is a psychedelic illicit drug that has recently been circulating in Japan. The aims of this study were (i) to optimise enzymatic hydrolysis conditions of the conjugated forms of N-OH-MDMA and its demethylated metabolite N-hydroxy-3,4-methylenedioxyamphetamine (N-OH-MDA), (ii) to investigate the urinary excretion profiles of N-OH-MDMA in rats, and (iii) to compare urinary excretion profiles of N-OH-MDMA and 3,4-methylenedioxymethamphetamine (MDMA). Conjugated forms of the N-hydroxylated compounds (N-OH-MDMA and N-OH-MDA) were almost successfully hydrolysed to their nonconjugated forms under anaerobic conditions after helium purging of the solution. The sum of N-OH-MDMA and N-OH-MDA was used to evaluate the amount of excreted N-hydroxylated metabolites because of degradation of N-OH-MDMA to N-OH-MDA during hydrolysis. Up to 24 h after oral administration of N-OH-MDMA oxalate, the main urinary metabolites were MDMA (14.3% of dose) and 3,4-MDA (7.7% of dose). Most of the N-hydroxylated forms were excreted as glucuronide conjugates. The total amount of N-hydroxylated metabolites after hydrolysis was 1.1% of dose. Urinary excretion profiles of MDMA were similar to that of N-OH-MDMA. It may be difficult to differentiate between abuse of MDMA and N-OH-MDMA by urine analysis.

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Section: Urinary Excretion Profiles After Oral N-oh-mdma Administratisupporting

confidence: 93%

Section: Introductionmentioning

confidence: 97%

Urinary excretion profiles ofN-hydroxy-3,4-methylenedioxymethamphetamine in rats

et al. 2011

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Simultaneous enantiomeric determination of MDMA and its phase I and phase II metabolites in urine by liquid chromatography–tandem mass spectrometry with chiral derivatization

et al. 2012

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A liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) procedure was developed for the simultaneous determination of enantiomers of the prevalent designer drug 3,4-methylenedioxymethamphetamine (MDMA) and its phase I and phase II metabolites in urine with chiral derivatization. The analytes in urine were directly derivatized with chiral Marfey's reagent, N(α)-(5-fluoro-2,4-dinitrophenyl)-D-leucinamide, without extraction. The diastereomers of the N(α)-(2,4-dinitrophenyl)-D-leucinamide derivatives generated were determined by LC-MS/MS. Satisfactory chromatographic separation was achieved for the enantiomers of MDMA and its metabolites 3,4-methylenedioxyamphetamine, 4-hydroxy-3-methoxymethamphetamine (HMMA), HMMA glucuronide, and HMMA sulfate on a semimicro octadecylsilane column using linear gradient elution. With use of multiple reaction monitoring mode, the limits of detection of these analytes ranged from 0.01 to 0.03 μg/mL. Linear calibration curves were obtained for all enantiomers from 0.1 to 20 μg/mL in urine. The method showed sufficient reproducibility and quantitative ability. This is the first report of a simple LC-MS/MS-based analytical procedure with direct chiral derivatization in aqueous media that allows simultaneous enantiomeric determination of drugs and their metabolites, including glucuronide and sulfate derivatives.

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Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement

Nakanishi¹,

Miki²,

Zaitsu³

et al. 2012

Forensic Science International

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Metabolism and Urinary Excretion of N-Hydroxy-3,4-methylenedioxymethamphetamine, a Recently Banned Narcotic in Japan

Cited by 3 publications

References 14 publications

Urinary excretion profiles ofN-hydroxy-3,4-methylenedioxymethamphetamine in rats

Urinary excretion profiles ofN-hydroxy-3,4-methylenedioxymethamphetamine in rats

Simultaneous enantiomeric determination of MDMA and its phase I and phase II metabolites in urine by liquid chromatography–tandem mass spectrometry with chiral derivatization

Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement

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