Characterization of hallucinogenic phenethylamines using high‐resolution mass spectrometry for non‐targeted screening purposes

Hallucinogenic phenethylamines such as 2,5-dimethoxyphenethylamines (2C-X) and their N-(2-methoxybenzyl) derivatives (25X-NBOMe) have seen an increase in novel analogues in recent years. These rapidly changing analogues make it difficult for laboratories to rely on traditional targeted screening methods to detect unknown new psychoactive substances (NPS). In this study, twelve 2C-X, six 2,5-dimethoxyamphetamines (DOX), and fourteen 25X-NBOMe derivatives, including two deuterated derivatives (2C-B-d6 and 25I-NBOMe-d9 ), were analyzed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-QTOF-MS). Collision-induced dissociation (CID) experiments were performed using collision energies set at 10, 20, and 40 eV. For 2C-X and DOX derivatives, common losses were observed including neutral and radical losses such as NH3 (17.0265 Da), •CH6 N (32.0500 Da), C2 H7 N (45.0578 Da) and C2 H9 N (47.0735 Da). 2C-X derivatives displayed common product ions at m/z 164.0837 ([C10 H12 O2 ]+• ), 149.0603 ([C9 H9 O2 ]+ ), and 134.0732 ([C9 H10 O]+• ) while DOX derivatives had common product ions at m/z 178.0994 ([C11 H14 O2 ]+• ), 163.0754 ([C10 H11 O2 ]+ ), 147.0804 ([C10 H11 O]+ ), and 135.0810 ([C9 H11 O]+ ). 25X-NBOMe had characteristic product ions at m/z 121.0654 ([C8 H9 O]+ ) and 91.0548 ([C7 H7 ]+ ) with minor common losses corresponding to 2-methylanisole (C8 H10 O, 122.0732 Da), 2-methoxybenzylamine (C8 H11 NO, 137.0847 Da), and •C9 H14 NO (152.1074 Da). Novel analogues of the selected classes can be detected by applying neutral loss filters (NLFs) and extracting the common product ions. Copyright © 2017 John Wiley & Sons, Ltd.