NMR Assignment of N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide Seized as Herbal Incense for the First Time in Italy

Jussara Amato,Vincenzo Compagnone,Antonio Randazzo,Fabiana Di Rosa,Giuseppe Peluso,Bruno Pagano,Nunzia Iaccarino,Ettore Novellino

doi:10.15744/2348-9804.1.403

Abstract

The synthetic cannabinoid, N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide, known also as AKB48 and/or APINACA, has been detected for the first time in herbal incense seized in Italy. Its structural characterization has been performed through gas chromatography-mass spectrometry (GC-MS) and high-resolution nuclear magnetic resonance (NMR) analysis. In order to favor an easier and faster identification of AKB48 in future investigations, NMR assignments in deuterated methanol and chloroform is also reported.

Highlights

Synthetic cannabinoids are chemicals that mimic the effect of Δ9-tetrahydrocannabinol (Δ9-THC), which is the principal psychoactive constituent of the cannabis plant
Following our continuous effort to oppose illegal drug trafficking [7], here we report the structural characterization of N-(1adamantyl)-1-pentyl-1H-indazole-3-carboxamide (Figure 1), known as AKB48 and/or APINACA, that has been detected for the first time in herbal incense seized in Italy
Five transparent plastic bags containing each ca. 1.5 g of herbal incense were seized in October 2012 in the city of Latina (Italy) from Italian military police (Carabinieri). 1.5 g of sample were extracted for 1 h at room temperature with methanol

Summary

Introduction

Synthetic cannabinoids are chemicals that mimic the effect of Δ9-tetrahydrocannabinol (Δ9-THC), which is the principal psychoactive constituent (cannabinoid) of the cannabis plant These chemicals are often added to a mixture of dried plant matter (e.g. herbs) and sold for smoking with names such as “Herbal incense” or “Spice” [1,2]. Tens of synthetic cannabinoids have been detected as psychoactive ingredients in herbal products or chemical powders around the world In this frame, and following our continuous effort to oppose illegal drug trafficking [7], here we report the structural characterization of N-(1adamantyl)-1-pentyl-1H-indazole-3-carboxamide (Figure 1), known as AKB48 and/or APINACA, that has been detected for the first time in herbal incense seized in Italy. In order to favor an easier and faster identification of AKB48 in the future investigations, NMR assignments in deuterated methanol and chloroform is reported

Materials and Methods

Results and Discussion

Conclusions