A technique combining trifluoroacetyl derivatization and gas chromatography–mass spectrometry to distinguish methamphetamine and its 4‐substituted analogs

Taniguchi, Masashi; Yamamoto, Yoshio; Nishi, Katsuji

doi:10.1002/jms.1851

Cited by 7 publications

(7 citation statements)

References 10 publications

(5 reference statements)

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“…To a solution of 1-5 mg of 2,4,6-TMPEA-NBOMe (1) in 0.4 ml acetonitrile 200 μl of trifluoroacetic anhydride was added (similar to [9,24,38,43] ). The mixture was kept in tightly closed vial at ambient temperature (20-23°C) during 10 min to obtain predominately mono-trifluoroacetic derivative 4 or 30 min at 70°C to obtain bis-trifluoroacetic derivative 5.…”

Section: Synthesis Of 246-tmpea-nbome Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…Applying GC/MS to study amphetamines of 2C and NBOMe series (as well as of the metabolites thereof) and to ensure their reliable determination and identification, their acyl and alkyl derivatives are often obtained. [8][9][10][11][12][13][14][15]22,24,38] In current investigation, we have prepared methyl (2), acetyl (3), trifluoroacetyl (4), bis-trifluoroacetyl (5) and dideutero (6) derivatives of 2,4,6-TMPEA-NBOMe (1) ( Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

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Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

et al. 2016

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Emergence of new psychoactive substances, hallucinogenic phenethylamines in particular, in illicit market is a serious threat to human health in global scale. We have detected and identified N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new compound in NBOMe series. Identification was achieved by means of gas chromatography/mass spectrometry (GC/MS), including high-resolution mass spectrometry with tandem experiments (GC/HRMS and GC/HRMS ), ultra-high performance liquid chromatography/high-resolution mass spectrometry with tandem experiments (UHPLC/HRMS and UHPLC/HRMS ), and H and C nuclear magnetic resonance spectroscopy. The peculiarities of fragmentation of the compound under electron ionization (EI) and collision-induced dissociation were studied. Despite of the empirical rule denying migration of the hydrogen atom in McLafferty rearrangement to the benzene ring with substituents in the both ortho-positions, it easily occurs for 2,4,6-TMPEA-NBOMe in EI conditions. We have noticed that electron-donating substituents, e.g. methoxy groups in the both ortho-positions and para-positions favor the rearrangement. For specially synthesized N-methyl and N-acyl derivatives McLafferty rearrangement is not observed. N-Acyl derivatives demonstrate McLafferty rearrangement, but the charge retains at the alternative fragment involving N-acyl carbonyl group. We have also showed that the hydrogen atoms in 2,4,6-trimethoxybenzene ring may be easily substituted for deuterium or for strong electrophiles like trifluoroacetyl. Analytical characteristics of 2,4,6-TMPEA-NBOMe and of some derivatives thereof which enable their determination in various criminal seizures are given. Copyright © 2016 John Wiley & Sons, Ltd.

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Section: Synthesis Of 246-tmpea-nbome Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

et al. 2016

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“…We previously reported a method for distinguishing currently controlled substances, such as MA, 4-MMA, and 4-FMA, from other uncontrolled 4-substituted MAs, including 4-chloromethamphetamine (4-CMA), 4-bromomethamphetamine (4-BMA), 4-iodomethamphetamine (4-IMA), and 4-nitromethamphetamine (4-NMA) [18]. As a way to circumvent existing drug laws, production and subsequent abuse of 4-CMA, 4-BMA and 4-NMA is expected in future because details of their psychotomi-metic properties and synthetic processes are easy to obtain online [19].…”

Section: Introductionmentioning

confidence: 99%

Comparative <i>in Vitro</i> Studies of the Metabolism of Six 4-Substituted Methamphetamines and Their Inhibition of Cytochrome P450 2D6 by GC-MS with Trifluoroacetyl Derivatization

Taniguchi

Yamamoto²,

Nishi³

2013

AJAC

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Use of new amphetamine-type stimulants (ATS) as designer drugs is a serious problem worldwide. ATS are used in tablet, capsule, and powder forms, and can be mixed with other drugs. There is little information available on how these new drugs are metabolized or their ability to inhibit the metabolism of co-administered drugs. This study aimed to investigate the metabolism of six 4-substituted analogs of methamphetamine (MA), and their potential inhibition of MA metabolism. The metabolism of MA and the 4-substituted MAs was examined in vitro using human metabolic enzymes. Metabolite analyses were performed using trifluoroacetyl derivatization and GC-MS. The experiments showed that cytochrome P450 2D6 (CYP2D6) was involved in the major metabolic pathway of MA, where it catalyzed N-demethylation of 4-fluoromethamphetamine (4-FMA), 4-chloromethamphetamine (4-CMA), 4-bromomethamphetamine (4-BMA), 4-iodomethamphetamine (4-IMA) and 4-nitromethamphetamine (4-NMA), and O-demethylation of 4-methoxymethamphetamine (4-MMA). The half maximal inhibitory concentration (IC 50 ) values for CYP2D6 using MA as substrate were different for each of the 4-substituted MAs. The strongest inhibitors of amphetamine production from MA were, in order, 4-IMA, 4-BMA, 4-CMA, 4-MMA, 4-FMA, and 4-NMA. The same order was observed for the IC 50 values for inhibition of p-hydroxymethamphetamine production from MA, except for the IC 50 of 4-MMA. The IC 50 values of 4-IMA were lower than the IC 50 values of fluoxetine and higher than that of quinidine. The results of this study imply that the risk of illicit drug interactions fluctuates so widely that unintentional fatal drug poisonings could occur.

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“…O teste multidrogas One Step (Inlab, São Luís, Brasil) foi utilizado para a triagem do uso de anfetaminas (valor de cut off de 1.000ng/mL). As amostras com resultados positivos foram então encaminhadas para confirmação, através de extração líquido-líquido e análise por cromatografia em fase gasosa acoplada a espectrometria de massas (CG-EM) 4 para a identificação da presença de anfetaminas (valor de cut off de 500ng/mL).…”

Section: Métodosunclassified

A continuidade do uso de anfetaminas por motoristas de caminhão no Estado de São Paulo, Brasil, a despeito da proibição de sua produção, prescrição e uso

et al. 2013

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Amphetamine use by truck drivers for occupational purposes is widely known. The production and consumption of amphetamines was banned by the Brazilian National Health Surveillance Agency (ANVISA) in October 2011. This study analyzes persistent amphetamine use by truck drivers since the ban was implemented. A convenience sample of 427 truck drivers was taken along highways in São Paulo State in 2012. Participants were asked to answer a structured questionnaire and provide a urine sample to screen for recent amphetamine consumption through toxicological analysis. Among the interviewed drivers, 7% had used some illicit drug recently and 2.7% had used amphetamines. Amphetamines are still consumed by truck drivers despite the risks and the recent ban. The authorities should thus monitor the possession and use of amphetamines by drivers in order to effectively enforce the ban.

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A technique combining trifluoroacetyl derivatization and gas chromatography–mass spectrometry to distinguish methamphetamine and its 4‐substituted analogs

Cited by 7 publications

References 10 publications

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

Comparative <i>in Vitro</i> Studies of the Metabolism of Six 4-Substituted Methamphetamines and Their Inhibition of Cytochrome P450 2D6 by GC-MS with Trifluoroacetyl Derivatization

A continuidade do uso de anfetaminas por motoristas de caminhão no Estado de São Paulo, Brasil, a despeito da proibição de sua produção, prescrição e uso

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A technique combining trifluoroacetyl derivatization and gas chromatography–mass spectrometry to distinguish methamphetamine and its 4‐substituted analogs

Cited by 7 publications

References 10 publications

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

Comparative &lt;i&gt;in Vitro&lt;/i&gt; Studies of the Metabolism of Six 4-Substituted Methamphetamines and Their Inhibition of Cytochrome P450 2D6 by GC-MS with Trifluoroacetyl Derivatization

A continuidade do uso de anfetaminas por motoristas de caminhão no Estado de São Paulo, Brasil, a despeito da proibição de sua produção, prescrição e uso

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Comparative <i>in Vitro</i> Studies of the Metabolism of Six 4-Substituted Methamphetamines and Their Inhibition of Cytochrome P450 2D6 by GC-MS with Trifluoroacetyl Derivatization