Analytical characterization of three hallucinogenic N‐(2‐methoxy)benzyl derivatives of the 2C‐series of phenethylamine drugs

Abstract

This publication reports analytical properties of three new hallucinogenic substances identified in blotter papers seized from the drug market, namely 25D-NBOMe [2-(2,5-dimethoxy-4-methylphenyl)-N-(2-methoxybenzyl)ethanamine], 25E-NBOMe [2-(4-ethyl-2,5-dimethoxyphenyl)-N-(2-methoxybenzyl)ethanamine] and 25G-NBOMe [2-(2,5-dimethoxy-3,4-dimethylphenyl)-N-(2-methoxybenzyl)ethanamine]. These substances are N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. The applied procedure covered a variety of analytical methods, including gas chromatography with electron impact mass spectrometry (GC-EI-MS; without derivatization and after derivatization with trifluoroacetic anhydride (TFAA)), liquid chromatography-electrospray ionization-quadrupole time of flight mass spectrometry (LC-ESI-QTOF-MS), Fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR), which made it possible to identify the active components unequivocally. The GC-MS spectra of analyzed compounds were very similar, with dominant ions observed at m/z = 150, 121, and 91. The remaining ions were analogous to those observed for parent substances, namely 2C-D, 2C-E, 2C-G, but their intensities were low. Derivatization allowed determination of molecular masses of the investigated substances. Their exact masses and chemical formulas were confirmed by LC-QTOF-MS experiments and the fragmentation patterns of these compounds following ESI were determined. The tandem mass spectrometry (MS/MS) experiments confirmed that the studied substances were N-(2-methoxy)benzyl derivatives of the 2C-series compounds. Final elucidation of the structures was performed by NMR spectroscopy. The substances were also characterized by FTIR spectroscopy to corroborate the identity of the compounds.

Analytical Validation of a Portable Mass Spectrometer Featuring Interchangeable, Ambient Ionization Sources for High Throughput Forensic Evidence Screening

“…Of note, MS/MS spectra obtained from NBOMe derivatives using the CIT of the AI-MS 1.2 demonstrated much higher complexity compared to that contained in the Wiley Registry of Tandem MS Data (Supplementary Figure S-8C), although there have been similar reports in recent literature [28,68,69]. It has been asserted that the addition of the N-(2-methoxy)benzyl group to the 2C-phenethylamine structure (another electron donating aromatic ring, as seen in Supplementary Figure S-8C) creates more favorable sites for dissociation that can occur along the -C-C-N-C-linkage chain, specifically C-C bond cleavage between the α-and β-carbon atoms on the ethylene bridge [68,69].…”

“…It has been asserted that the addition of the N-(2-methoxy)benzyl group to the 2C-phenethylamine structure (another electron donating aromatic ring, as seen in Supplementary Figure S-8C) creates more favorable sites for dissociation that can occur along the -C-C-N-C-linkage chain, specifically C-C bond cleavage between the α-and β-carbon atoms on the ethylene bridge [68,69]. The complexity and intensity to which these fragmentation patterns are seen is highly dependent on the MS/MS conditions utilized [44], which leads to the inter-instrument variations reported [66,70].…”

Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs)

“…Of particular interest are N-2-methoxybenzyl-phenethylamines (NBOMe drugs), which are novel and reportedly very potent hallucinogens that have been increasingly used recreationally (Forrester, 2014;Hill et al, 2013;Ninnemann and Stuart, 2013;Rose et al, 2013;Walterscheid et al, 2014;Wood et al, 2015;Zuba, 2012), with additional potential use as radiotracers (Ettrup et al, 2011;Ettrup et al, 2010). Recreationally used NBOMe drugs include 25I-NBOMe, 25C-NBOMe, 25B-NBOMe, and 25D-MBOMe (Armenian and Gerona, 2014;Poklis et al, 2014;Rose et al, 2013), which are derivatives of 2,5-dimethoxy-4-substituted phenethylamines (2C drugs; Dean et al, 2013;Hill and Thomas, 2011;Shulgin and Shulgin, 1991).…”

Découverte d’un laboratoire de conditionnement de nouveaux produits de synthèse en France

“…Le spectre de masse de la RH-34 (figure 5) montre, comme pour les autres composés de la famille des NBOMe, les fragments de masse 121, 91 et 150 correspondant à l'ion méthoxy-benzyle, l'ion benzyle résultant de la perte du groupement mé-thoxyle, et l'ion résultant du clivage de la liaison C-N [12,17].…”