Characterization of the recently detected cathinone N-cyclohexyl butylone: From structure elucidation to in silico supported pharmacological/toxicological considerations

Abstract

One of the most widely consumed new psychoactive substances (NPS) families in Europe are synthetic cathinones. Cathinone structure can be easily modified resulting in new derivatives that rapidly reach drug markets. In this work, the recently detected synthetic cathinone N-cyclohexyl butylone has been characterized by gas chromatography coupled to mass spectrometry (GC–MS), liquid chromatography coupled to high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) and Fourier-transformed infrared (FTIR) spectroscopy, using research chemicals samples collected by the drug analysis service Energy Control from anonymous users. Compound identification was performed by the combination of HRMS and NMR data. The elemental composition and putative moieties of the compound were determined based on the accurate-mass ions observed by HRMS. Then, different NMR experiments, including bidimensional, allowed the establishment of the chemical structure and confirmation of compound identity. Furthermore, FTIR spectrum was also acquired in order to provide a complete analytical characterization of the novel cathinone. Finally, pharmacological/toxicological characterization was attempted using in silico methods. Based on these predictions, N-cyclohexyl butylone probably has similar effects to stimulants like MDMA.