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

Abstract

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.

The Use of Single Crystal X-Ray Diffraction Technique for Characterization of 25I-NBOMe and 25R-NBOH (R = Cl, I, Br, Et) in Forensic Application

“…For example, these bands are quite present in cellulose, the main constituent of blotter papers. 41 Furthermore, unlike reported in the literature, 29 it is not possible to clearly visualize a double peak at 1250 cm -1 related to the substitution by OH of the N-benzyl group in Figure 4a. This was probably due to a large amount of impurities present in these samples.…”

“…[20][21][22][23] Raman spectroscopy proved very useful and has been extensively employed to rapidly determine drug abuse, such as hand luggage control for aircraft passengers. 14,[24][25][26][27][28] NMR also has been used in NPS characterization; 29 however, it is an expensive equipment and only laboratories with good financial resources can carry out this analysis.…”

Analysis of 2,5-dimethoxy-amphetamines and 2,5-dimethoxy-phenethylamines aiming their determination in biological matrices: a review

“…In the last years, other NBOH drugs (4-bromo-2,5-dimethoxy- N -(2-hydroxybenzyl)phenethylamine 25B-NBOH, 4-chloro-2,5-dimethoxy- N -(2-hydroxybenzyl)phenethylamine 25C-NBOH, 4-ethyl-2,5-dimethoxy- N -(2-hydroxybenzyl)phenethylamine 25E-NBOH and 2,5-dimethoxy- N -(2-hydroxybenzyl)phenethylamine 25H-NBOH) were identified in blotter papers in Brazil [ 37 ] and Singapore [ 38 ].…”

The new psychoactive substances 25H-NBOMe and 25H-NBOH induce abnormal development in the zebrafish embryo and interact in the DNA major groove

“…In fact, unlike NBOMes/NBOHs, LSD and ecstasy are rarely directly attributable to death. Moreover, knowledge about the toxicology of LSD or ecstasy, or even cocaine, is well established ( Alvarenga et al, 2010 , Barenys et al, 2009 , Dishotsky et al, 1971 , Jih-Heng and Lih-Fang, 1998 , Nichols and Grob, 2018 , Polifka and Friedman, 1991 ), while very limited or practically non-existent data are reported for NBOMes/NBOHs ( Arantes et al, 2017 , de Barros et al, 2021a , Machado et al, 2020 ). 25I-NBOMe was detected, after death, in blood (from 0.04 to 0.95 nM), urine (6.69 nM), vitreous humor (0.23 nM); 25C-NBOMe was detected in blood (1.49 nM) and urine (6.85 nM), and 25B-NBOMe detected in blood samples (4.18 nM) ( Andreasen et al, 2015 , Kueppers and Cooke, 2015 , Lowe et al, 2015 , Morini et al, 2017 , Poklis et al, 2014 , Shanks et al, 2015 , Tang et al, 2014 ).…”