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Casale JF, Hays PA.
“Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues - Part I”.
Microgram Journal. 2012;9(2):84-109.
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Abstract
ABSTRACT: The characterization of eleven 2,5-dimethoxy-N-(2-methoxybenzyl) phenethylamine (NBOMe) derivatives and their 3- and 4-methoxybenzyl analogues via mass spectrometry and infrared spectrometry is presented. Analytical data is presented to differentiate these positional isomers.
A number of highly potent hallucinogenic phenethylamine derivatives have been encountered by law enforcement within the past year. These designer drugs are commonly referred to as “NBOMe” compounds; their structures are depicted in Figure 1 (compounds 1, 4, 7, 10, 13, 16, 19, 22, 25, 28, and 31). They are N-(2-methoxy)benzyl derivatives of the “2C compounds” (2,5-dimethoxyphenethylamines with various substituents at C-4), first made popular as a result of their publication in PIHKAL [1]. The NBOMe series was first investigated by Heim and co-workers [2] as agonists for the 5-HT2A serotonin receptors that are associated with hallucinogenic activity, and later by Braden et al. as “superpotent” agonists for those receptors [3]. Although there have been no scientific studies on the potency of these derivatives, several illicit drug-related Internet websites recommend sub-milligram (microgram) doses, on par with LSD. Violent physical/mental episodes and deaths have been attributed to the abuse of these compounds [4, 5]. The NBOMe compounds are illicitly distributed as either uncut powders or diluted to sub-milligram doses laced into perforated blotter paper. Due to their extreme potency, forensic chemists must take great care to prevent accidental self-dosing during routine chemical analysis.
Except for three NBOMe derivatives [6], there currently is little or no spectroscopic or spectrometric data in the literature on these compounds. Herein, we report the synthesis, characterization, and differentiation of 11 commonly encountered 2,5-dimethoxy-N-(2-methoxybenzyl)phenethyl-amine (NBOMe) derivatives from their 3- and 4-methoxy-benzyl analogues (Figure 1) via mass spectrometry and infrared spectroscopy. Nuclear magnetic resonance spectroscopy of these compounds will be the subject of a later report.
Key Words: hallucinogens, NBOMe, 25H-NBOMe, 25B-NBOMe, 25C-NBOMe, 25D-NBOMe, 25E-NBOMe, 25I-NBOMe, 25N-NBOMe, 25P-NBOMe, 25T2-NBOMe, 25T4-NBOMe, 25T7-NBOMe, designer drugs, synthesis, characterization, forensic chemistry.
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