Identification of the cannabimimetic AM-1220 and its azepane isomer (N-methylazepan-3-yl)-3-(1-naphthoyl)indole in a research chemical and several herbal mixtures |
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Authors: | Stefan Kneisel Philippe Bisel Volker Brecht Sebastian Broecker Michael Müller Volker Auw?rter |
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Institution: | 1. Institute of Forensic Medicine, University Medical Center Freiburg, Albertstr. 9, 79104, Freiburg, Germany 2. Institute of Pharmaceutical Sciences, Albert-Ludwigs-Universit?t Freiburg, Albertstr. 25, 79104, Freiburg, Germany 3. Institute of Legal Medicine, University Hospital Charit?? Berlin, Turmstr. 21, 10559, Berlin, Germany
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Abstract: | Recently, a large number of synthetic cannabinoids have been identified in herbal mixtures. Moreover, an even higher number
of cannabimimetic compounds are currently distributed as research chemicals on a gram to kilogram scale via several online
trading platforms. As this situation leads to a large number of new cannabimimetics and the occurrence of isobaric substances,
the analysis of such compounds using mass spectroscopy (MS) involves the risk of incorrect assignments of mass spectra. In
certain cases, this leads to considerable analytical challenges. In the majority of cases, these challenges can only be mastered
by combining multiple analytical techniques. We purchased a so-called research chemical advertised as the cannabimimetic compound
(N-methylpiperidin-2-yl)methyl]-3-(1-naphthoyl)indole (AM-1220) via an Internet platform. Analysis of the microcrystalline substance
using gas chromatography (GC)–MS indicated the presence of pure AM-1220. However, after further purity testing utilizing thin-layer
chromatography we were surprised to see an additional spot indicating a mixture of two substances with highly similar physicochemical
properties. After isolation, high-resolution mass spectroscopy (HR-MS) revealed an elemental composition of C26H26N2O for both substances, proving the presence of two isobaric substances. Moreover, GC–MS and LC-HR-MS/MS experiments indicated
two naphthoylindoles featuring different heterocyclic substituents at the indole nitrogen. Nuclear magnetic resonance spectroscopy
verified the presence of the highly potent cannabimimetic AM-1220 and its azepane isomer. Interestingly, only a few weeks
after purchasing the powder we also detected both substances in a similar proportion in several herbal mixtures for the first
time. |
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