Identification of the synthetic cannabinoid N-(2-phenyl-propan-2-yl)-1-(4-cyanobutyl)-1H-indazole-3-carboxamide (CUMYL-4CN-BINACA) in a herbal mixture product

Abstract

We were the first to detect N-(2-phenylpropan-2-yl)-1-(4-cyanobutyl)-1H-indazole-3-carboxamide (common name CUMYL-4CN-BINACA) as a new synthetic cannabinoid, on the illegal market in Bursa, Turkey. To elucidate the chemical structure, the dried herbal mixture was extracted with methanol. The extract was purified by column chromatography. Pure compound was analyzed by gas chromatography–mass spectrometry (GC–MS), attenuated total reflection Fourier-transform infrared spectroscopy (FT-IR), and one- and two-dimensional nuclear magnetic resonance (NMR) spectroscopy. The GC–MS, FT-IR and 1H and 13C NMR spectra of the compound coincided well with the reference data. All protons and carbons were assigned by their couplings and correlations observed in 1H-1H correlation spectroscopy, 1H-13C heteronuclear multiple bond correlation, and 1H-13C heteronuclear single quantum coherence spectra. On the basis of the spectral data, the compound was identified as CUMYL-4CN-BINACA. Herewith, we report analytical characteristics of CUMYL-4CN-BINACA enabling its (and possible analogues thereof) determination in criminal seizures.