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Synthesis and determination of analytical characteristics and differentiation of positional isomers in the series of N-(2-methoxybenzyl)-2-(dimethoxyphenyl)ethanamine using chromatography-mass spectrometry.

Drug testing and analysis (2020-05-18)
Olga V Kupriyanova, Vadim A Shevyrin, Yuri M Shafran, Albert T Lebedev, Vasili A Milyukov, Vladimir L Rusinov
ABSTRACT

N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamines (NBOMes) are synthetic phenethylamine derivatives emerging on the global drug market and reported to be associated with untoward effects in people who use drugs. Its action involves agonism at serotonin 5-HT2A receptors, affecting cognitive and behavioral processes. However, certain isomers of NBOMes may not show any psychoactive effects. They are not controlled by legislation and can be tested as pharmaceutical drugs. This study deals with the differentiation among positional isomers of 25H-NBOMe differing in the position of the two methoxy groups in the phenylethyl moiety of the molecule, using chromatography-mass spectrometry methods. The gas chromatography analysis showed that the isothermal mode was more efficient than the usually applied temperature-programming mode for the separation of the mentioned isomers. Electron ionization mass spectra of 25H-NBOMe isomers were highly similar, often resulting in a high probability of erroneous identification. However, mass spectra of their trifluoroacetyl or pentafluoropropanoyl derivatives were easily identified as they contained fragments with many significant differences. The proposed analysis using liquid chromatography-tandem mass spectrometry could distinguish the isomers of 25H-NBOMe without the need for any derivatization.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium borohydride, ReagentPlus®, 99%
Sigma-Aldrich
Trifluoroacetic anhydride, ReagentPlus®, ≥99%
Sigma-Aldrich
Hydrogen chloride, ReagentPlus®, ≥99%
Sigma-Aldrich
3,4-Dimethoxybenzaldehyde, 99%
Sigma-Aldrich
2-Methoxybenzaldehyde, 98%
Sigma-Aldrich
2,4-Dimethoxybenzaldehyde, 98%
Sigma-Aldrich
3,5-Dimethoxybenzaldehyde, 98%
Sigma-Aldrich
2,3-Dimethoxybenzaldehyde, 98%
Sigma-Aldrich
2,6-Dimethoxybenzaldehyde, 99%

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