Analytical characterization of four new ortho‐methoxybenzylated amphetamine‐type designer drugs

Abstract

In a seizure of German custom authorities four N-(ortho-methoxybenzyl)amines with amphetamine partial structure were obtained as pure compounds: N-(ortho-methoxybenzyl)-3,4-dimethoxyamphetamine (3,4-DMA-NBOMe (1)), N-(ortho-methoxybenzyl)-4-ethylamphetamine (4-EA-NBOMe (2)), N-(ortho-methoxybenzyl)-4-methylmethamphetamine (4-MMA-NBOMe (3)), and N-(ortho-methoxybenzyl)-5-(2-aminopropyl)benzofuran (5-APB-NBOMe (4)). The compounds have been detected in Germany for the first time and no analytical data had been previously published. Mass spectrometric (MS), infrared (IR) spectroscopic, and nuclear magnetic resonance (NMR) spectroscopic data are presented. Copyright © 2015 John Wiley & Sons, Ltd.

Mass spectrometric properties ofN-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (2,4,6-TMPEA-NBOMe), a new representative of designer drugs of NBOMe series and derivatives thereof

“…Further structural modifications consisted in position of the methoxy group (a part of N ‐methoxybenzyl moiety), replacing of a methoxy group by 2,3‐methylenedioxy or hydroxy groups, or increasing a number of methoxy groups in benzene ring . Another approach to new NBOMes involves a replacement of 2,5‐dimethoxybenzene for benzofurane (5‐APB‐NBOMe), 4‐alkylbenzene, 3,4‐dimethoxybenzene or 3,4,5‐trimethoxybenzene (mescaline‐NBOMe) …”

“…Although there are many analytical data enabling identification of NBOMes and the metabolites thereof in the literature, 2,4,6‐TMPEA‐NBOMe ( 1 ) (or its isomer, mescaline‐NBOMe) was never described from analytical point of view. To the best of our knowledge, current work is the first scientific report on 2,4,6‐TMPEA‐NBOMe ( 1 ).…”

“…[35] Another approach to new NBOMes involves a replacement of 2,5-dimethoxybenzene for benzofurane (5-APB-NBOMe), 4-alkylbenzene, 3,4-dimethoxybenzene or 3,4,5trimethoxybenzene (mescaline-NBOMe). [21,36] In October 2015, we have detected in illicit market a representative of NBOMe with modified design, namely N-(2-methoxybenzyl)-2-(2,4,6-trimethoxyphenyl)ethanamine (conventionally named as 2,4,6-TMPEA-NBOMe) (1). Among known NBOMes, the closest analog of compound 1 is its isomer, N-(2-methoxybenzyl)-2-(3,4,5trimethoxyphenyl)ethanamine (mescaline-NBOMe), for which the data on its interaction with serotonin receptors are published.…”

The analysis of illicit 25X‐NBOMe seizures in Western Australia

“…In recent years there have been numerous publications relating to the identification of new and novel illicit drugs from a wide range of chemical classes; including cathinones, tryptamines and phenylethylamines, along with the identification of novel synthetic cannabinoids. [1][2][3][4] One group of compounds that has received widespread attention is the N-(2-methoxy) benzyl derivatives of well-known phenylethylamines such as 2C-I and 2C-C. [5][6][7][8] This class of compounds is generally named using the abbreviation for the phenylethylamine (such as 2C-I) combined with the NBOMe acronym representing the N-(2-methoxy)benzyl moiety (for example 2C-I-NBOMe, also known as 25I-NBOMe). 7,9 Several recent deaths attributed to NBOMe-related compounds have received coverage in the press both in Australia and internationally.…”

Identification of five substituted phenethylamine derivatives 5‐MAPDB, 5‐AEDB, MDMA methylene homolog, 6‐Br‐MDMA, and 5‐APB‐NBOMe

“…[22][23][24][25] 6-Br-MDMA (4) has been detected in Europe and reported by the EMCDDA in 2014. [26] Our paper added the high resolution LC-MS data and presented the NMR data with a different deuterated solvent to make the analytical properties of 5 more exhaustive. The GC-MS, NMR, and IR data of 5-APB-NBOMe (5) have been recently reported by Westphal et al, but without high resolution LC-MS data.…”