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Analysis of 25I-NBOMe, 25B-NBOMe, 25C-NBOMe and other dimethoxyphenyl-N-[(2-methoxyphenyl) methyl]ethanamine derivatives on blotter paper
2C-NBOMe (Item No. 9001096) is an analytical reference standard that is structurally categorized as a phenethylamine. 25C-NBOMe is a derivative of 2C-C having an N-(2-methoxybenzyl) addition at the amine. 2C-C is a known hallucinogen that stimulates monoamine receptor activity and inhibits the re-uptake of serotonin and norepinephrine in rat brain synaptosomes (IC50 = 31 and 63 μM, respectively).1,2 The N-(2-methoxybenzyl) addition to 2C-NBOMe increases the affinity and selectivity for the 5-HT2A receptor over other serotonin receptors.3 Radiolabeled 25C-NBOMe has been used for positron emission tomography imaging of the 5-HT2A receptor in porcine brain.4 This product is intended for forensic and research uses.
In recent years, N-methoxybenzyl-methoxyphenylethylamine (NBOMe) derivatives, a class of designer hallucinogenic drugs, have become popular drugs of abuse. These drugs have been the cause of severe intoxications and even deaths. They act as 5-HT2A receptors agonists and have been reported to produce serotonin-like syndrome with bizarre behavior, severe agitation and seizures persisting for as long as 3 days. The most commonly reported derivatives are 25I-NBOMe, 25B-NBOMe and 25C-NBOMe, respectively 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl) methyl]ethanamine, N-(2-methoxybenzyl)-2,5-dimethoxy-4-bromophenethylamine and N-(2-methoxybenzyl)-2,5-dimethoxy-4-chlorophenethylamine. Like many low dose hallucinogenic drugs these compounds are often sold on blotter paper. Three different types of commercially available blotter papers reported to contain NBOMe derivatives were obtained. These blotter papers were screened using Direct Analysis in Real Time AccuTOFTM mass spectrometry followed by confirmation and quantification by high-performance liquid chromatography triple quadrapole mass spectrometry. The major drug present on each of the three blotter products was different, 25I-NBOMe, 25C-NBOMe or 25B-NBOMe. The blotter papers were also found to have minute amounts of two or three NBOMe derivative impurities of 25H-NBOMe, 25I-NBOMe, 25C-NBOMe, 25B-NBOMe and/or 25D-NBOMe.
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