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

Forensic Toxicology

Volumn 34, Issue 2, 2016, Pages 344-352

  Andernach, Lars ^a   Pusch, Stefan ^a   Weber, Carina ^a   Schollmeyer, Dieter ^a   Münster Müller, Sascha ^b   Pütz, Michael ^b   Opatz, Till ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b Federal Criminal Office (Bundeskriminalamt)   (Germany)

Author keywords

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

Indexed keywords

CANNABINOID; METHYLDIMETHYLBUTANOATE CYCLOHEXYLMETHYLINDOLE CARBOXAMIDE; PSYCHOTROPIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL COMPOSITION; CHIRAL CHROMATOGRAPHY; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; ENANTIOMER; HERB; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LUXEMBOURG; PRIORITY JOURNAL; SPICE; X RAY CRYSTALLOGRAPHY;

EID: 84973111294     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-016-0321-1     Document Type: Article

References (34)

1. 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 44:832–837
2. 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 57:439–441
3. EMCDDA (2015) European drug report 2015: trends and developments. http://www.emcdda.europa.eu/system/files/publications/974/TDAT15001ENN.pdf. Accessed January 2016
4. 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 108:534–544
5. 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 6:832–839
6. EMCDDA (2015) EMCDDA––Europol 2014 annual report on the implementation of council decision 2005/387/JHA. Implementation reports. http://www.emcdda.europa.eu/system/files/publications/1018/TDAN15001ENN.pdf. Accessed January 2016
7. 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 407:6301–6315
8. 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 34:94–107
9. 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. 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 40:86–87
11. 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 40:240–242
12. UNODC (2015) Global SMART update––synthetic cannabinoids: key facts about the largest and most dynamic group of NPS. https://www.unodc.org/documents/scientific/Global_SMART_Update_13_web.pdf. Accessed January 2016
13. BtMÄndV, implied in German narcotics law (BtMG) since November 21st, 2015, BGBl. 1 S. 1992
14. 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. Cody JT (1992) Determination of methamphetamine enantiomer ratios in urine by gas chromatography–mass spectrometry. J Chromatogr 580:77–95
16. Kristensen K, Christensen CB, Christrup LL (1994) The mu1, mu2, delta, kappa opioid receptor binding profiles of methadone stereoisomers and morphine. Life Sci 56:45–50
17. Pop E (2000) Nonpsychotropic synthetic cannabinoids. Curr Pharm Design 6:1347–1359
18. 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 20:4918–4921
19. 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 29:2176–2179
20. Stewart JP (2007) Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements. J Mol Model 13:1173–1213
21. 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 58:1200–1211
22. 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 37:785–789
23. Becke AD (1993) Density-functional thermochemistry. III. The role of exact exchange. J Chem Phys 98:5648–5652
24. 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 56:2257–2261
25. 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 98:11623–11627
26. Hariharan PC, Pople JA (1973) The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 28:213–222
27. 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 72:650–654
28. 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 252:211–220
29. 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 464:211–226
30. Tomasi J, Mennucci B, Cammi R (2005) Quantum mechanical continuum solvation models. Chem Rev 105:2999–3094
31. Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G (2013) SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. Chirality 25:243–249
32. Bruhn T, Schaumlöffel A, Hemberger Y (2015) SpecDis, Version 1.65. University of Würzburg, Würzburg
33. Sheldrick G (2015) SHELX––integrated space-group and crystal-structure determination. Acta Crystallogr A 71:3–8
34. Sheldrick G (2015) Crystal structure refinement with SHELXL. Acta Crystallogr C 71:3–8