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.