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, 9 (1), 8314

Characterization of a Recently Detected Halogenated Aminorex Derivative: para-fluoro-4-methylaminorex (4'F-4-MAR)

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Characterization of a Recently Detected Halogenated Aminorex Derivative: para-fluoro-4-methylaminorex (4'F-4-MAR)

D Fabregat-Safont et al. Sci Rep.

Abstract

Despite the fact that 33% of the new psychoactive substances seized in 2015 were synthetic cathinones, the number of these derivatives has been decreasing in the last years, probably as a consequence of the unfavourable effects reported by users. Thus, the list of possible cathinone analogues is expected to get shorter, and it is likely that the same moiety changes applied for the preparation of synthetic cathinones will be applied in the near future to other stimulants in the search for favourable alternatives to controlled substances. This is evidenced by the increase in newly reported substances belonging to stimulant classes other than cathinones. One of the possible candidates for a new backbone from which to base new stimulants is aminorex, which is classified as a Schedule I substance by the Drug Enforcement Administration. Three derivatives have been reported until now: 4-methylaminorex or 4-MAR (also categorized as a Schedule I substance), para-methyl-4-methylaminorex (4,4'-DMAR) and 3',4'-methylenedioxy-4-methylaminorex (MDMAR). Recently, the new halogenated 4-MAR derivative, para-fluoro-4-methylaminorex, characterised in this work (and abbreviated as pF-4-methylaminorex or 4'F-4-MAR) was detected by the Slovenian police. In the present work, 4'F-4-MAR has been characterized by high resolution mass spectrometry and nuclear magnetic resonance in a sample obtained from an anonymous consumer. This research shows that the same modifications applied for the preparation of synthetic cathinones are being used to prepare new stimulants based on the aminorex backbone.

Conflict of interest statement

The authors declare no competing interests.

Figures

Figure 1
Figure 1
Structure of aminorex and its reported derivatives, including the new derivative reported in this work.
Figure 2
Figure 2
Structure of methcathinone and its reported derivatives.
Figure 3
Figure 3
UHPLC-HRMS information of the putative aminorex derivative. (A) Low energy spectrum. (B) High energy spectrum. (C) Proposed fragmentation pathway once identified the new aminorex derivative.
Figure 4
Figure 4
Two-dimension NMR experiments, with signal assignation, performed for the identification of the novel aminorex derivative. (A) COSY spectrum. (B) HSCQ spectrum.

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