Degradation of N-hydroxy-3,4-methylenedioxymethamphetamine in aqueous solution and its prevention

Tsujikawa, Kenji; Kuwayama, Kenji; Miyaguchi, Hajime; Kanamori, Tatsuyuki; Iwata, Yuko; Inoue, Hiroyuki

doi:10.1016/j.forsciint.2009.09.020

Cited by 7 publications

(6 citation statements)

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“…N-OH-MDMA oxalate and N-OH-MDA (free base) were previously synthesised in our laboratory (Tsujikawa et al, 2009). MDMA hydrochloride and MDA hydrochloride were synthesised according to the previously reported methods (Shulgin and Shulgin, 1992).…”

Section: Methodsmentioning

confidence: 99%

“…Extraction of the metabolites (N-OH-MDMA, N-OH-MDA, MDMA, and MDA) was performed by our previously reported method with minor modifications (Tsujikawa et al, 2009). To 200 µL of the hydrolysed or non-hydrolysed urine solution (100 µL of the urine + 100 µL of the citrate buffer), 800 µL of distilled water and 1 mL of 0.5 mol/L sodium carbonate buffer (pH 10.0, containing 0.2% (w/v) l-ascorbic acid) were added.…”

Section: Quantitative Analysis Of the N-oh-mdma Metabolites In The Urinementioning

confidence: 99%

“…The peak intensity of N-OH-MDA was also increased by hydrolysis even though the peaks corresponding to N-OH-MDA-glucuronide and -sulphate were not observed in the direct analysis. Because N-OH-MDA is one of the degradation products of N-OH-MDMA in alkaline solution (Tsujikawa et al, 2009), it was supposed that this increase of N-OH-MDA was caused by degradation of N-OH-MDMA during hydrolysis.…”

Section: Direct Analysis Of the Conjugated Forms Of N-oh-mdma And N-omentioning

confidence: 99%

“…N-OH-MDMA and N-OH-MDA are easily degraded in neutral-to-basic solution, but this degradation can be prevented by addition of l-ascorbic acid (Tsujikawa et al, 2009) or by replacement of oxygen in the solution with argon (Uchiyama et al, 2009). Consequently, it is necessary to investigate hydrolysis conditions, especially the effect of oxygen removal, before examination of the urinary excretion profiles.…”

Section: Introductionmentioning

confidence: 99%

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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: Methodsmentioning

confidence: 99%

Section: Quantitative Analysis Of the N-oh-mdma Metabolites In The Urinementioning

confidence: 99%

Section: Direct Analysis Of the Conjugated Forms Of N-oh-mdma And N-omentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2011

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“…From the data obtained, absorbance vs pH curve was plotted (Figure 2). Also values of pH end point , pK a and pH working range were determined using mL vs pH and mL vs ∆E/∆V graphs [9].…”

Section: Chemicals and Instrumentationsmentioning

confidence: 99%

<b>A triazole derivative as a new acid-base indicator</b>

Bulut

Duran

Gündoğdu

et al. 2010

Bull. Chem. Soc. Eth.

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ABSTRACT ABSTRACT. In this study a new pH indicator, 3-benzyl-4-p-nitrobenzylidenamino-4,5-dihydro-1,2,4-triazole-5-on (BPNBAT), soluble in acetonitrile:water (1:4), was developed. The estimation of pH is possible either from the position of the absorption maxima or from the absorbance intensity at a constant wavelength. This feature allowed us to determine the basic transition range of the medium because BPNBAT is colorless at pH lower than 8.5 and showed strong yellow-green color with high extinction coefficient in the pH range of 8.5-10.1. pKa, pH at equivalent point and the molar absorptivity (in the aqueous medium at 380 nm) of BPNBAT are determined as 9.3, 8.3 and 8.8 x 10 3 L.mol, respectively. The color change at the transition range can be attributed to the resonance structures of BPNBAT. The triazole compound was compared with thymolphthalein for accuracy test. KEY WORDS KEY WORDS KEY WORDS

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On the Frontier: Analytical Chemistry and the Occurrence of Illicit Drugs into Surface Waters in the United States

Jones-Lepp

Alvarez

Loganathan

2011

Illicit Drugs in the Environment

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Degradation of N-hydroxy-3,4-methylenedioxymethamphetamine in aqueous solution and its prevention

Cited by 7 publications

References 7 publications

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

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

<b>A triazole derivative as a new acid-base indicator</b>

On the Frontier: Analytical Chemistry and the Occurrence of Illicit Drugs into Surface Waters in the United States

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