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Forensic Toxicology

, Volume 34, Issue 2, pp 344–352 | Cite as

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

  • Lars Andernach
  • Stefan Pusch
  • Carina Weber
  • Dieter Schollmeyer
  • Sascha Münster-Müller
  • Michael Pütz
  • Till Opatz
Original Article

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.

Keywords

MDMB-CHMICA Synthetic cannabinoids New psychoactive substances Chiroptical spectroscopy X-ray crystallography Chiral HPLC 

Notes

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.

Compliance with ethical standards

Conflict of interest

There are no financial or other relations that could lead to a conflict of interest.

Ethical approval

This article does not contain any studies with human participants or animals performed by any of the authors.

Supplementary material

11419_2016_321_MOESM1_ESM.pdf (4.7 mb)
Supplementary material 1 (PDF 4805 kb)

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Copyright information

© Japanese Association of Forensic Toxicology and Springer Japan 2016

Authors and Affiliations

  • Lars Andernach
    • 1
  • Stefan Pusch
    • 1
  • Carina Weber
    • 1
  • Dieter Schollmeyer
    • 1
  • Sascha Münster-Müller
    • 2
  • Michael Pütz
    • 2
  • Till Opatz
    • 1
  1. 1.Institute of Organic ChemistryJohannes Gutenberg University MainzMainzGermany
  2. 2.Bundeskriminalamt–Federal Criminal Police Office (BKA), Forensic Science Institute, KT 34-ToxicologyWiesbadenGermany

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