Characterization of the synthetic cannabinoid MDMB-CHMCZCA

Carina Weber, Stefan Pusch, Dieter Schollmeyer, Sascha Münster-Müller, Michael Pütz and Till Opatz
Beilstein J. Org. Chem. 2016, 12, 2808–2815.

Supporting Information

Supporting Information File 1: NMR spectra, UV and ECD spectra, IR and VCD spectra, HPLC/ESI-MSn, chiral HPLC, and computational chemistry.
Format: PDF Size: 4.1 MB Download
Supporting Information File 2: Chemical information file of compound (S)-3.
CCDC 1521512 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
Format: CIF Size: 612.7 KB Download

Cite the Following Article

Characterization of the synthetic cannabinoid MDMB-CHMCZCA
Carina Weber, Stefan Pusch, Dieter Schollmeyer, Sascha Münster-Müller, Michael Pütz and Till Opatz
Beilstein J. Org. Chem. 2016, 12, 2808–2815.

How to Cite

Weber, C.; Pusch, S.; Schollmeyer, D.; Münster-Müller, S.; Pütz, M.; Opatz, T. Beilstein J. Org. Chem. 2016, 12, 2808–2815. doi:10.3762/bjoc.12.279

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 779.7 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Groß, J.; Kühlborn, J.; Pusch, S.; Weber, C.; Andernach, L.; Renzer, G.; Eckhardt, P.; Brauer, J.; Opatz, T. Comparison of different density functional theory methods for the calculation of vibrational circular dichroism spectra. Chirality 2023, 35, 753–765. doi:10.1002/chir.23580
  • Er, A.; Çelik, S. The Uses of Cannabinoids in Medicine and Their Spectroscopic Applications. Medical Cannabis and the Effects of Cannabinoids on Fighting Cancer, Multiple Sclerosis, Epilepsy, Parkinson's, and Other Neurodegenerative Diseases; IGI Global, 2023; pp 235–257. doi:10.4018/978-1-6684-5652-1.ch010
  • Dobšíková, K.; Spálovská, D.; Kuchař, M.; Paškanová, N.; Setnička, V. Indazole-derived synthetic cannabinoids: Absolute configuration determination and structure characterization by circular dichroism and DFT calculations. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2023, 291, 122373. doi:10.1016/j.saa.2023.122373
  • Dobšíková, K.; Javorská, Ž.; Paškan, M.; Spálovská, D.; Trembulaková, P.; Herciková, J.; Kuchař, M.; Kozmík, V.; Kohout, M.; Setnička, V. Enantioseparation and a comprehensive spectroscopic analysis of novel synthetic cathinones laterally substituted with a trifluoromethyl group. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 2023, 291, 122320. doi:10.1016/j.saa.2023.122320
  • Morales-Noé, A.; Esteve-Turrillas, F. A.; Armenta, S. Metabolism of third generation synthetic cannabinoids using zebrafish larvae. Drug testing and analysis 2021, 14, 594–603. doi:10.1002/dta.3195
  • Hehet, P.; Köke, N.; Zahn, D.; Frömel, T.; Rößler, T.; Knepper, T. P.; Pütz, M. Synthetic cannabinoid receptor agonists and their human metabolites in sewage water: Stability assessment and identification of transformation products. Drug testing and analysis 2021, 13, 1758–1767. doi:10.1002/dta.3129
  • Filer, C. N. Chirality in Cannabinoid Research. Cannabis and cannabinoid research 2021, 6, 1–4. doi:10.1089/can.2020.0027
  • Spálovská, D.; Paškan, M.; Jurásek, B.; Kuchař, M.; Kohout, M.; Setnička, V. Structural spectroscopic study of enantiomerically pure synthetic cathinones and their major metabolites. New Journal of Chemistry 2021, 45, 850–860. doi:10.1039/d0nj05065b
  • Antonides, L. H.; Cannaert, A.; Norman, C.; NicDaeid, N.; Sutcliffe, O. B.; Stove, C. P.; McKenzie, C. R. M. Shape matters: The application of activity-based in vitro bioassays and chiral profiling to the pharmacological evaluation of synthetic cannabinoid receptor agonists in drug-infused papers seized in prisons. Drug testing and analysis 2020, 13, 628–643. doi:10.1002/dta.2965
  • Jones, N. S.; Comparin, J. H. Interpol review of controlled substances 2016–2019. Forensic science international. Synergy 2020, 2, 608–669. doi:10.1016/j.fsisyn.2020.01.019
  • de Castro, J. S.; Rodrigues, C. H. P.; Bruni, A. T. IN SILICO INFRARED CHARACTERIZATION OF SYNTHETIC CANNABINOIDS BY QUANTUM CHEMISTRY AND CHEMOMETRICS. Journal of chemical information and modeling 2020, 60, 2100–2114. doi:10.1021/acs.jcim.9b00871
  • Alam, R. M.; Keating, J. J. Adding more “spice” to the pot: A review of the chemistry and pharmacology of newly emerging heterocyclic synthetic cannabinoid receptor agonists. Drug testing and analysis 2020, 12, 297–315. doi:10.1002/dta.2752
  • Potts, A.; Cano, C.; Thomas, S.; Hill, S. Synthetic cannabinoid receptor agonists: classification and nomenclature. Clinical toxicology (Philadelphia, Pa.) 2019, 58, 82–98. doi:10.1080/15563650.2019.1661425
  • Münster-Müller, S.; Hansen, S. P.; Opatz, T.; Zimmermann, R.; Pütz, M. Chemical profiling of the synthetic cannabinoid MDMB-CHMICA: Identification, assessment, and stability study of synthesis-related impurities in seized and synthesized samples. Drug testing and analysis 2019, 11, 1192–1206. doi:10.1002/dta.2652
  • Gaunitz, F.; Dahm, P.; Mogler, L.; Thomas, A.; Thevis, M.; Mercer-Chalmers-Bender, K. In vitro metabolic profiling of synthetic cannabinoids by pooled human liver microsomes, cytochrome P450 isoenzymes, and Cunninghamella elegans and their detection in urine samples. Analytical and bioanalytical chemistry 2019, 411, 3561–3579. doi:10.1007/s00216-019-01837-8
  • Antonides, L. H.; Cannaert, A.; Norman, C.; Vives, L.; Harrison, A.; Costello, A.; Daeid, N. N.; Stove, C. P.; Sutcliffe, O. B.; McKenzie, C. R. M. Enantiospecific Synthesis, Chiral Separation, and Biological Activity of Four Indazole-3-Carboxamide-Type Synthetic Cannabinoid Receptor Agonists and Their Detection in Seized Drug Samples. Frontiers in chemistry 2019, 7, 321. doi:10.3389/fchem.2019.00321
  • Münster-Müller, S.; Zimmermann, R.; Pütz, M. A Novel Impurity-Profiling Workflow with the Combination of Flash-Chromatography, UHPLC-MS, and Multivariate Data Analysis for Highly Pure Drugs: A Study on the Synthetic Cannabinoid MDMB-CHMICA. Analytical chemistry 2018, 90, 10559–10567. doi:10.1021/acs.analchem.8b02679
  • Banister, S. D.; Connor, M. The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution. Handbook of experimental pharmacology 2018, 252, 191–226. doi:10.1007/164_2018_143
  • Mogler, L.; Franz, F.; Wilde, M.; Huppertz, L. M.; Halter, S.; Angerer, V.; Moosmann, B.; Auwärter, V. Phase I metabolism of the carbazole-derived synthetic cannabinoids EG-018, EG-2201, and MDMB-CHMCZCA and detection in human urine samples. Drug testing and analysis 2018, 10, 1417–1429. doi:10.1002/dta.2398
  • Angerer, V.; Mogler, L.; Steitz, J. P.; Bisel, P.; Hess, C.; Schoeder, C. T.; Müller, C. E.; Huppertz, L. M.; Westphal, F.; Schäper, J.; Auwärter, V. Structural characterization and pharmacological evaluation of the new synthetic cannabinoid ‘CUMYL-PEGACLONE’. Drug testing and analysis 2017, 10, 597–603. doi:10.1002/dta.2237
Other Beilstein-Institut Open Science Activities