Identification of new NBOH drugs in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH

Purpose The recreational drug market remains dynamic. After the introduction of 25I-NBOH, an N -benzylphenethylamine and new psychoactive substance, as option for LSD and NBOMe drugs, new NBOH substances have been identified in recent years. Herein, we report our efforts for the identification and structural elucidation of three new NBOHs detected in seized blotter papers: 25B-NBOH, 25C-NBOH, and 25E-NBOH. Methods Blotter papers seized between 2017 and 2018 by local police force in Brazil were submitted to extraction, purification, identification and characterization using attenuated total reflectance-Fourier transform infrared spectroscopy, gas chromatography—mass spectrometry, liquid chromatography—tandem mass spectrometry, and one- and two-dimensional nuclear magnetic resonance spectroscopy. Results Three new NBOHs were characterized: 2-(((4-ethyl-2,5-dimethoxyphenethyl)amino)methyl)phenol (25E-NBOH, 2C-E-NBOH), 2-(((4-chloro-2,5-dimethoxyphenethyl)amino)methyl)phenol (25C-NBOH, 2C-C-NBOH), and 2-(((4-bromo-2,5-dimethoxyphenethyl)amino)methyl)phenol (25B-NBOH, 2C-B-NBOH). Conclusions To our knowledge, this is the first report for identification and detailed characterization of 25B-NBOH, 25C-NBOH, and 25E-NBOH in seized samples. NBOH substances are not under United Nations Conventions control. The identification of seized blotter papers between 2014 and beginning of 2019 showed that NBOH substances have become the main hallucinogenic drug in the region. These group are thermolabile under gas chromatographic conditions, demanding other analytical approaches of analysis to avoid misidentifications. Unfortunately, the knowledge about toxicology of NBOHs are limited.