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

Three new hallucinogenic substances—25D-NBOMe, 25E-NBOMe, and 25G-NBOMe—were identified in blotter papers seized from the drug market. These are N-(2-methoxy)benzyl derivatives of the 2C-series of phenethylamine drugs. A range of analytical methods, including gas chromatography-mass spectrometry, liquid chromatography-mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance, unequivocally identified the active components. The GC-MS spectra showed very similar dominant ions at m/z = 150, 121, and 91, with other ions analogous to those of the parent 2C compounds but at low intensities. Derivatization helped determine molecular masses, and exact masses and chemical formulas were confirmed by LC-QTOF-MS. Tandem mass spectrometry confirmed the N-(2-methoxy)benzyl derivative structures, and NMR provided final structural elucidation. FTIR spectroscopy corroborated compound identities.

Study at a glance

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.