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Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products

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Abstract

A seized sample of the synthetic cannabinoid MDMB-CHMICA was studied by means of vibrational and electronic circular dichroism spectroscopy and found to have (S)-configuration by comparison of the experimental spectra with density functional theory calculations. We were able to additionally confirm the absolute configuration was additionally confirmed using X-ray crystallography. Furthermore, the title compound was extracted from five commercially available “Spice-like” herbal mixtures. The extracts were all found to have the same absolute configuration as the seized sample and all analyzed samples were found to be of very high optical purity as judged by chiral high-performance liquid chromatography.

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Acknowledgments

The authors thank Prof. Pol Besenius (Mainz) for granting access to the ECD spectrometer, the Zentrum für Datenverarbeitung (Mainz) for access to the MOGON supercomputer, and Dr. Serge Schneider, Laboratoire National de Santé, Luxembourg, for arranging the transfer of samples of an MDMB-CHMICA customs seizure to BKA. S.P. is grateful for a scholarship from the Fonds der Chemischen Industrie. This work was performed within the research project ‘‘SPICE-Profiling’’ (agreement no. JUST/2013/ISEC/DRUGS/AG/ISEC/4000006421) funded by the European Union′s program ‘‘Fight Against and Prevention of Crime’’ (ISEC). The contents of the paper are the sole responsibility of the authors and can in no way be taken to reflect the views of the European Commission.

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    Authors and Affiliations

    1. Institute of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, 55128, Mainz, Germany

      Lars Andernach, Stefan Pusch, Carina Weber, Dieter Schollmeyer & Till Opatz

    2. Bundeskriminalamt–Federal Criminal Police Office (BKA), Forensic Science Institute, KT 34-Toxicology, Äppelallee 45, 65203, Wiesbaden, Germany

      Sascha Münster-Müller & Michael Pütz

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    1. Lars Andernach
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    2. Stefan Pusch
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    Correspondence to Michael Pütz.

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    L. Andernach and S. Pusch contributed equally.

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    Andernach, L., Pusch, S., Weber, C. et al. Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products. Forensic Toxicol 34, 344–352 (2016). https://doi.org/10.1007/s11419-016-0321-1

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