3-Naphthoylindazoles and 2-naphthoylbenzoimidazoles as novel chemical groups of synthetic cannabinoids: Chemical structure elucidation, analytical characteristics and identification of the first representatives in smoke mixtures

•New synthetic cannabinoids are detected in smoke mixtures.•The structures of three new synthetic cannabinoids are determined.•The compounds discovered are referred to new groups of cannabinoids.•Reliable methods of determination of new synthetic cannabinoids are elaborated.•HRMS, HRMS/MS, NMR and FT-IR spectra of new cannabinoids are presented.

By means of gas chromatography with mass spectrometry detection (GC–MS), including high resolution mass spectrometry (GC–HRMS) together with ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC–HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR), structure of novel synthetic cannabinoids, namely, 1-(5-fluoropentyl)-1H-indazol-3-yl(naphthalen-1-yl)methanone, naphthalen-1-yl(1-pentyl-1H-benzo[d]imidazol-2-yl)methanone and 1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl(naphthalen-1-yl)methanone was established. Analytical data obtained in the paper enable reliable identification of these compounds during qualitative analysis of seizures, including smoke mixtures.