Indazole-derived synthetic cannabinoids: Absolute configuration determination and structure characterization by circular dichroism and DFT calculations

K Dobšíková; D Spálovská; M Kuchař; N Paškanová; V Setnička

doi:10.1016/j.saa.2023.122373

Indazole-derived synthetic cannabinoids: Absolute configuration determination and structure characterization by circular dichroism and DFT calculations

Spectrochim Acta A Mol Biomol Spectrosc. 2023 Apr 15:291:122373. doi: 10.1016/j.saa.2023.122373. Epub 2023 Jan 14.

Authors

K Dobšíková¹, D Spálovská², M Kuchař³, N Paškanová⁴, V Setnička²

Affiliations

¹ Department of Analytical Chemistry, University of Chemistry and Technology, Technická 5, Prague 6, 166 28, Czech Republic. Electronic address: kristyna.dobsikova@vscht.cz.
² Department of Analytical Chemistry, University of Chemistry and Technology, Technická 5, Prague 6, 166 28, Czech Republic.
³ Forensic Laboratory of Biologically Active Substances, Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technická 5, Prague 6, 166 28, Czech Republic; National Institute of Mental Health, Topolová 748, Klecany 250 67, Czech Republic.
⁴ Forensic Laboratory of Biologically Active Substances, Department of Chemistry of Natural Compounds, University of Chemistry and Technology, Technická 5, Prague 6, 166 28, Czech Republic.

PMID: 36657287
DOI: 10.1016/j.saa.2023.122373

Abstract

An increasing number of products containing synthetic cannabinoids pose a growing crisis to public health worldwide. Recently, a rising number of cases of serious adverse health effects, intoxications, and death cases associated with synthetic cannabinoids were reported. The current study represents the comprehensive structural analysis of three new synthetic cannabinoids (AB-, ADB- and AMB-FUBINACA) in solution investigated by electronic and vibrational circular dichroism together with the conventional methods of infrared and ultraviolet absorption spectroscopy, all supported by the density functional theory (DFT) calculations. The best level of theory to reproduce the experimental wavenumbers and wavelengths was found to be the B3PW91 method with a 6-311++G(d,p) basis set including the implicit solvent effect simulation. Very good agreement between the experimental and simulated spectra allowed us to determine the absolute configuration and a detailed interpretation of the IR absorption, VCD, ECD and UV spectra of AB-, ADB- and AMB-FUBINACA. In addition, the HOMO and LUMO electronic transitions were calculated.

Keywords: Chiroptical spectroscopy; DFT calculation; Drugs; Synthetic cannabinoids; Vibrational spectroscopy.

MeSH terms

Cannabinoids*
Circular Dichroism
Density Functional Theory

Substances

Cannabinoids