Identification and Analytical Characterization of a Novel Synthetic Cannabinoid-Type Substance in Herbal Material in Europe.

Emmanouil D Tsochatzis,Margaret V Holland,Fabiano Reniero,Claude Guillou,Giovanni Palmieri,Joao Alberto Lopes

doi:10.3390/molecules26040793

Emmanouil D Tsochatzis, Margaret V Holland + Show 4 more

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https://doi.org/10.3390/molecules26040793

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Abstract

The rapid diffusion of new psychoactive substances (NPS) presents unprecedented challenges to both customs authorities and analytical laboratories involved in their detection and characterization. In this study an analytical approach to the identification and structural elucidation of a novel synthetic cannabimimetic, quinolin-8-yl-3-[(4,4-difluoropiperidin-1-yl) sulfonyl]-4-methylbenzoate (2F-QMPSB), detected in seized herbal material, is detailed. An acid precursor 4-methyl-3-(4,4-difluoro-1-piperidinylsulfonyl) benzoic acid (2F-MPSBA), has also been identified in the same seized material. After extraction from the herbal material the synthetic cannabimimetic, also referred to as synthetic cannabinoid receptor agonists or “synthetic cannabinoids”, was characterized using gas chromatography-mass spectrometry (GC-MS), 1H, 13C, 19F and 15N nuclear magnetic resonance (NMR) and high-resolution tandem mass spectrometry (HR-MS/MS) combined with chromatographic separation. A cheminformatics platform was used to manage and interpret the analytical data from these techniques.

Highlights

Recent studies have reported a significant increase in the number of novel psychoactive substances (NPS) within the EU recreational drug market [1,2,3,4,5,6]
The current study presents the application of this workflow to the chemical characterization of the new synthetic cannabinoid 2F-quinolinyl-4methyl-3-(1-piperidinylsulfonyl) benzoate (QMPSB) (quinolin-8-yl 3-((4,4-difluoropiperidin1-yl)sulfonyl)-4-methylbenzoate) (Figure S1), which was identified in three different samples of herbal material which were found, together with several other synthetic cannabinoids, in a postal parcel seized by customs control authorities
Through peak picking analysis and interpretation of the mass spectra using the ACD/Spectrus algorithms, it was revealed that the peak at tR = 17.54 min refers to the potential synthetic cannabinoid-type substance 2F-QMPSB and the peak at tR = 5.38 min initially looked as if it could be 4,4-difluoropiperidine (m/z 121)

Summary

Introduction

Recent studies have reported a significant increase in the number of novel psychoactive substances (NPS) within the EU recreational drug market [1,2,3,4,5,6]. The authorities are struggling to keep up with the surge in these substances of abuse Their accessibility via the internet, e-shops and social-networking sites, where they are often mislabeled as “bath salts” or “herbal extracts”, plays a major role in their marketing, sale and distribution. An example of this was seen in the seizure of plant material containing QMPSB, which was packaged and labeled as herbal incense [9,10,11,12,13,14,15,16,17,18,19,20]. Many attempts have been made to try to reduce the production of such products, marketed as potpourri, herbal tea or “Spice”, and all containing synthetic cannabinoids [9,19]

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