Identification of a new class of thermolabile psychoactive compounds, 4-substituted 2-(4-X-2, 5-dimethoxyphenyl)-N-[(2-hydroxyphenyl)methyl]ethanamine (25X-NBOH, X = Cl, Br, or I) by gas chromatography-mass spectrometry using chemical derivatization by heptafluorobutyric anhydride (HFBA)

Abstract

4-Substituted 2-(4-X-2,5-dimethoxyphenyl)-N-[(2-hydroxyphenyl)methyl] ethanamine (25X-NBOH, X = Cl, Br, or I) are new psychoactive substances (NPS). Identification of these NBOH analogues by gas chromatography-mass spectrometry is difficult because they are found in very low concentrations in the blotting paper in which they are sold, and because of the thermolabile nature of NBOH. In the ion source of a mass spectrometer they break down to the known NPS 2,5-dimethoxy-4-Xphenethylamine (2C-X) thereby giving no indication of the initial compound present. We identify 25XNBOH by heptafluorobutyric anhydride (HFBA) derivatization and subsequent mass spectrometric analysis. The major peak is the bis-derivative where both the amine and phenol are derivatized, with a minor peak of the mono-derivative in which only the amine is derivatized. There is a small amount of degradation of 25X-NBOH to the 2C-X amine which is then derivatized to the amide in-situ. Reaction with HFBA is an efficient and simple derivatization that works well with NBOH and NBOMe analogs and is recommended for routine forensic analysis.