A phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP), newly detected in illicit products

Abstract

Two new psychoactive substances (NPSs), a phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD, 1) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP, 2), were identified in illicit products distributed from January to March 2015 in Japan. The identification was based on liquid chromatography–mass spectrometry (LC–MS), gas chromatography–mass spectrometry (GC–MS), high-resolution MS and nuclear magnetic resonance (NMR) analyses. Compound 1 has a 3,4-methylenedioxybenzyl moiety that is an analog of N-benzylmethoxy derivatives of 2,5-dimethoxyphenethylamines (“NBOMe”-compounds), e.g., 25I-NBOMe. Compound 2 is a difluoromethylenedioxy analog of the known designer drug 1-(3,4-methylenedioxybenzyl)piperazine (MDBP). To our knowledge, this is the first report of compounds 1 and 2 detected as NPSs in illicit products. Although there is no chemical or pharmaceutical information for compound 1, a 2,3-methylenedioxy isomer of 1, 25I-NBMD, was reported to have a binding affinity for 5-HT_2A receptor. In the GC–MS and LC–MS analyses, compound 1 (25I-NB34MD) showed spectra that are very similar to those of the isomer 25I-NBMD. The structure of compound 1 was determined here by an NMR analysis. Considering these results, we should be careful when analyzing NPSs in illicit products to prevent their misidentification as isomers of other NPSs. It is important to directly compare an unknown substance with an authentic substance by using multiple instruments such as GC–MS and LC–MS.