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Published in: Forensic Toxicology 2/2016

01-07-2016 | Original Article

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

Authors: Lars Andernach, Stefan Pusch, Carina Weber, Dieter Schollmeyer, Sascha Münster-Müller, Michael Pütz, Till Opatz

Published in: Forensic Toxicology | Issue 2/2016

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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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Literature
1.
go back to reference Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) ‘Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837CrossRefPubMed Auwärter V, Dresen S, Weinmann W, Müller M, Pütz M, Ferreirós N (2009) ‘Spice’ and other herbal blends: harmless incense or cannabinoid designer drugs? J Mass Spectrom 44:832–837CrossRefPubMed
2.
go back to reference Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441CrossRefPubMed Uchiyama N, Kikura-Hanajiri R, Kawahara N, Haishima Y, Goda Y (2009) Identification of a cannabinoid analog as a new type of designer drug in a herbal product. Chem Pharm Bull 57:439–441CrossRefPubMed
4.
go back to reference Hermanns-Clausen M, Kneisel S, Szabo B, Auwärter V (2013) Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. Addiction 108:534–544CrossRefPubMed Hermanns-Clausen M, Kneisel S, Szabo B, Auwärter V (2013) Acute toxicity due to the confirmed consumption of synthetic cannabinoids: clinical and laboratory findings. Addiction 108:534–544CrossRefPubMed
5.
go back to reference Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal 6:832–839CrossRefPubMed Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2014) Changes in the prevalence of new psychoactive substances before and after the introduction of the generic scheduling of synthetic cannabinoids in Japan. Drug Test Anal 6:832–839CrossRefPubMed
7.
go back to reference Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT (2015) Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal Bioanal Chem 407:6301–6315CrossRefPubMed Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT (2015) Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal Bioanal Chem 407:6301–6315CrossRefPubMed
8.
go back to reference Langer N, Lindigkeit R, Schiebel H-M, Papke U, Ernst L, Beuerle T (2016) Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015. Forensic Toxicol 34:94–107CrossRef Langer N, Lindigkeit R, Schiebel H-M, Papke U, Ernst L, Beuerle T (2016) Identification and quantification of synthetic cannabinoids in “spice-like” herbal mixtures: update of the German situation for the spring of 2015. Forensic Toxicol 34:94–107CrossRef
9.
go back to reference Franz F, Schwörer N, Angerer V, Moosmann B, Auwärter V (2015) Metabolism and urine analysis of the new synthetic cannabinoid MDMB-CHMICA. Toxichem Krimtech 82:192–198 Franz F, Schwörer N, Angerer V, Moosmann B, Auwärter V (2015) Metabolism and urine analysis of the new synthetic cannabinoid MDMB-CHMICA. Toxichem Krimtech 82:192–198
10.
go back to reference Westin AA, Frost J, Brede WR, Gundersen POM, Einvik S, Aarset H, Slørdal L (2016) Sudden cardiac death following use of the synthetic cannabinoid MDMB-CHMICA. J Anal Toxicol 40:86–87PubMed Westin AA, Frost J, Brede WR, Gundersen POM, Einvik S, Aarset H, Slørdal L (2016) Sudden cardiac death following use of the synthetic cannabinoid MDMB-CHMICA. J Anal Toxicol 40:86–87PubMed
11.
go back to reference Angerer V, Franz F, Schwarze B, Moosmann B, Auwärter V (2016) Reply to ‘sudden cardiac death following use of the synthetic cannabinoid MDMB-CHMICA’. J Anal Toxicol 40:240–242CrossRefPubMed Angerer V, Franz F, Schwarze B, Moosmann B, Auwärter V (2016) Reply to ‘sudden cardiac death following use of the synthetic cannabinoid MDMB-CHMICA’. J Anal Toxicol 40:240–242CrossRefPubMed
13.
go back to reference BtMÄndV, implied in German narcotics law (BtMG) since November 21st, 2015, BGBl. 1 S. 1992 BtMÄndV, implied in German narcotics law (BtMG) since November 21st, 2015, BGBl. 1 S. 1992
14.
go back to reference Pütz M, Schneiders S, Auwärter V, Münster-Müller S, Scheid N (2015) The EU-project ′SPICE-profiling′ (2015–2017)––objectives and results of a first study on Spice products containing 5F-PB-22. Toxichem Krimtech 82:273–283 Pütz M, Schneiders S, Auwärter V, Münster-Müller S, Scheid N (2015) The EU-project ′SPICE-profiling′ (2015–2017)––objectives and results of a first study on Spice products containing 5F-PB-22. Toxichem Krimtech 82:273–283
15.
go back to reference Cody JT (1992) Determination of methamphetamine enantiomer ratios in urine by gas chromatography–mass spectrometry. J Chromatogr 580:77–95CrossRef Cody JT (1992) Determination of methamphetamine enantiomer ratios in urine by gas chromatography–mass spectrometry. J Chromatogr 580:77–95CrossRef
16.
go back to reference Kristensen K, Christensen CB, Christrup LL (1994) The mu1, mu2, delta, kappa opioid receptor binding profiles of methadone stereoisomers and morphine. Life Sci 56:45–50CrossRef Kristensen K, Christensen CB, Christrup LL (1994) The mu1, mu2, delta, kappa opioid receptor binding profiles of methadone stereoisomers and morphine. Life Sci 56:45–50CrossRef
18.
go back to reference Kiyoi T, York M, Francis S, Edwards D, Walker G, Houghton AK, Cottney JE, Baker J, Adam JM (2010) Design, synthesis, and structure–activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists. Bioorg Med Chem Lett 20:4918–4921CrossRefPubMed Kiyoi T, York M, Francis S, Edwards D, Walker G, Houghton AK, Cottney JE, Baker J, Adam JM (2010) Design, synthesis, and structure–activity relationship study of conformationally constrained analogs of indole-3-carboxamides as novel CB1 cannabinoid receptor agonists. Bioorg Med Chem Lett 20:4918–4921CrossRefPubMed
19.
go back to reference Fulmer GR, Miller AJM, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI (2010) NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics 29:2176–2179CrossRef Fulmer GR, Miller AJM, Sherden NH, Gottlieb HE, Nudelman A, Stoltz BM, Bercaw JE, Goldberg KI (2010) NMR chemical shifts of trace impurities: common laboratory solvents, organics, and gases in deuterated solvents relevant to the organometallic chemist. Organometallics 29:2176–2179CrossRef
20.
go back to reference Stewart JP (2007) Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Model 13:1173–1213CrossRefPubMedPubMedCentral Stewart JP (2007) Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Model 13:1173–1213CrossRefPubMedPubMedCentral
21.
go back to reference Vosko SH, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58:1200–1211CrossRef Vosko SH, Wilk L, Nusair M (1980) Accurate spin-dependent electron liquid correlation energies for local spin density calculations: a critical analysis. Can J Phys 58:1200–1211CrossRef
22.
go back to reference Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789CrossRef Lee C, Yang W, Parr RG (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B 37:785–789CrossRef
23.
go back to reference Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652CrossRef Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652CrossRef
24.
go back to reference Hehre WJ, Ditchfield R, Pople JA (1972) Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257–2261CrossRef Hehre WJ, Ditchfield R, Pople JA (1972) Self-consistent molecular orbital methods. XII. Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 56:2257–2261CrossRef
25.
go back to reference Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98:11623–11627CrossRef Stephens PJ, Devlin FJ, Chabalowski CF, Frisch MJ (1994) Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields. J Phys Chem 98:11623–11627CrossRef
26.
go back to reference Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28:213–222CrossRef Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28:213–222CrossRef
27.
go back to reference Krishnan R, Binkley JS, Seeger R, Pople JA (1980) Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys 72:650–654CrossRef Krishnan R, Binkley JS, Seeger R, Pople JA (1980) Self-consistent molecular orbital methods. XX. A basis set for correlated wave functions. J Chem Phys 72:650–654CrossRef
28.
go back to reference Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ (1996) Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 252:211–220CrossRef Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ (1996) Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 252:211–220CrossRef
29.
go back to reference Tomasi J, Mennucci B, Cancès E (1999) The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J Mol Struc-Theochem 464:211–226CrossRef Tomasi J, Mennucci B, Cancès E (1999) The IEF version of the PCM solvation method: an overview of a new method addressed to study molecular solutes at the QM ab initio level. J Mol Struc-Theochem 464:211–226CrossRef
30.
go back to reference Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094CrossRefPubMed Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094CrossRefPubMed
31.
go back to reference Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G (2013) SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25:243–249CrossRefPubMed Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G (2013) SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25:243–249CrossRefPubMed
32.
go back to reference Bruhn T, Schaumlöffel A, Hemberger Y (2015) SpecDis, Version 1.65. University of Würzburg, Würzburg Bruhn T, Schaumlöffel A, Hemberger Y (2015) SpecDis, Version 1.65. University of Würzburg, Würzburg
33.
go back to reference Sheldrick G (2015) SHELX––integrated space-group and crystal-structure determination. Acta Crystallogr A 71:3–8CrossRef Sheldrick G (2015) SHELX––integrated space-group and crystal-structure determination. Acta Crystallogr A 71:3–8CrossRef
34.
go back to reference Sheldrick G (2015) Crystal structure refinement with SHELXL. Acta Crystallogr C 71:3–8CrossRef Sheldrick G (2015) Crystal structure refinement with SHELXL. Acta Crystallogr C 71:3–8CrossRef
Metadata
Title
Absolute configuration of the synthetic cannabinoid MDMB-CHMICA with its chemical characteristics in illegal products
Authors
Lars Andernach
Stefan Pusch
Carina Weber
Dieter Schollmeyer
Sascha Münster-Müller
Michael Pütz
Till Opatz
Publication date
01-07-2016
Publisher
Springer Japan
Published in
Forensic Toxicology / Issue 2/2016
Print ISSN: 1860-8965
Electronic ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-016-0321-1

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