Identification of three cannabimimetic indazole and pyrazole derivatives, APINACA 2H-indazole analogue, AMPPPCA, and 5F-AMPPPCA

Drug Testing and Analysis

Volumn 9, Issue 2, 2017, Pages 248-255

  Jia, Wei ^a   Meng, Xin ^a   Qian, Zhenhua ^a   Hua, Zhendong ^a   Li, Tao ^a   Liu, Cuimei ^a  

^a INSTITUTE OF FORENSIC SCIENCE   (China)

Author keywords

5F AMPPPCA; AMPPPCA; APINACA 2H indazole analogue; new psychoactive substance; synthetic cannabinoid

Indexed keywords

COPYRIGHTS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

5F-AMPPPCA; AMPPPCA; ANALYTICAL PROPERTIES; APINACA 2H-INDAZOLE ANALOG; CANNABIMIMETIC; CARBOXAMIDES; INDAZOLE; NEW PSYCHOACTIVE SUBSTANCE; PYRAZOLE DERIVATIVES; SYNTHETIC CANNABINOID;

GAS CHROMATOGRAPHY;

(1 ADAMANTYL) 1 (5 FLUOROPENTYL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; AMIDE; CANNABINOID; INDAZOLE DERIVATIVE; N (1 ADAMANTYL) 4 METHYL 1 PENTYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; N(1 ADAMANTYL) 2 PENTYL 2H INDAZOLE 3 CARBOXAMIDE 2H INDAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ADAMANTANE; N-(1-ADAMANTYL)-1-PENTYLINDAZOLE-3-CARBOXAMIDE; PSYCHOTROPIC AGENT; STREET DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG IDENTIFICATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MEASUREMENT ACCURACY; PROTON NUCLEAR MAGNETIC RESONANCE; QUADRUPOLE MASS SPECTROMETRY; TIME OF FLIGHT MASS SPECTROMETRY; ANALOGS AND DERIVATIVES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ADAMANTANE; CANNABINOIDS; CHROMATOGRAPHY, LIQUID; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INDAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PSYCHOTROPIC DRUGS; PYRAZOLES; STREET DRUGS;

EID: 84960362363     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1967     Document Type: Article

References (33)

1. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). New psychoactive substances in Europe. An update from the EU Early Warning System. Lisbon. 2015. Available at: http://www.emcdda.europa.eu/publications/2015/new-psychoactive-substances [May 2015].
2. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). European drug report 2014: trends and developments. Lisbon. 2014. Available at: http://idpc.net/publications/2014/05/european-drug-report-2014-trends-and-developments [May 2014].
3. S. D. Brandt, L. A. King, M. Evans-Brown. The new drug phenomenon. Drug Test. Anal. 2014, 6, 587.
4. Synthetics Monitoring: Analyses, Reporting and Trends (SMART). Global SMART update: legal responses to NPS: multiple approaches to a multi-faceted problem. 2015. Available at: http://www.unodc.org/documents/scientific/Global_SMART_Update_14-web.pdf [September 2015].
5. China Food and Drug Administration (CFDA). The supplementary catalogue of non-medical use narcotic drugs and psychotropic substances control list. 2015. Available at: http://www.sfda.gov.cn/directory/web/WS01/images/t8fSqdPDwODC6dft0qnGt7rNvqvJ8dKpxre53NbGxrfW1tT2srnEv8K8LmRvY3g=.docx [29 September 2015].
6. D. R. Compton, K. C. Rice, B. R. De Costa, R. K. Razdan, L. S. Melvin, M. R. Johnson, B. R. Martin. Cannabinoid structure-activity relationships: correlation of receptor binding and in vivo activities. J. Pharmacol. Exp. Ther. 1993, 265, 218.
7. 2 receptors: steric and electronic effects of naphthoyl substituents. New highly selective CB2 receptor agonists. Bioorgan. Med. Chem. 2005, 13, 89.
8. C. L. Chin, A. E. Tovcimak, V. P. Hradil, T. R. Seifert, P. R. Hollingsworth, P. Chandran, C. Z. Zhu, D. Gauvin, M. Pai, J. Wetter, G. C. Hsieh, P. Honore, J. M. Frost, M. J. Dart, M. D. Meyer, B. B. Yao, B. F. Cox, G. B. Fox. Differential effects of cannabinoid receptor agonists on regional brain activity using pharmacological MRI. Brit. J. Pharmacology. 2008, 153, 367.
9. J. W. Huffman. Cannabimimetic Indoles, Pyrroles, and Indenes: Structure-Activity Relationships and Receptor Interactions. The Cannabinoid Receptors, Humana Press, NewYork 2009, pp. 49–94.
10. L. Console-Bram, J. Marcu, M. E. Abood. Cannabinoid receptors: nomenclature and pharmacological principles. Prog. Neuro-Psychopharmacol. Biol. Psychiatry. 2012, 38, 4.
11. S.D. Banister, M. Moir, J. Stuart, R.C. Kevin, K.E. Wood, M. Longworth, S.M. Wilkinson, C. Beinat, A.S. Buchanan, M. Glass, M. Connor, I.S. McGregor, M. Kassiou. Pharmacology of indole and indazole synthetic cannabinoid designer drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADBPINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA. ACS.Chem. Neurosci. 2015, DOI:http://dx.doi.org/10.1021/acschemneuro.5b00112
12. P. Jankovics, A. Váradi, L. Tólgyesi, S. Lohner, J. Németh-Palotás, J. Balla. Detection and identification of the potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary. Forensic Sci. Int. 2012, 214, 27.
13. N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, Y. Goda. Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1H-indazole-3-carboxamide (APINACA), and detection of five synthetic cannabinoids, AM-1220, AM-2233, AM-1241, CB-13 (CRA-13), and AM-1248, as designer drugs in illegal products. Forensic Toxicol. 2012, 30, 114.
14. [14] N. Uchiyama, M. Kawamura, R. Kikura-Hanajiri, Y. Goda. URB-754: A new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci. Int. 2013, 227, 21.
15. R. Kikura-Hanajiri, N. Uchiyama, M. Kawamura, Y. Goda. Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol. 2013, 31, 44.
16. D. Zuba, B. Byrska. Analysis of the prevalence and coexistence of synthetic cannabinoids in ‘herbal high’ products in Poland. Forensic Toxicol. 2013, 31, 21.
17. N. Uchiyama, S. Matsuda, M. Kawamura, R. Kikura-Hanajiri, Y. Goda. Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products. Forensic Toxicol. 2013, 31, 223.
18. N. Uchiyama, S. Matsuda, D. Wakana, R. Kikura-Hanajiri, Y. Goda. New cannabimimetic indazole derivatives, N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indazole-3-carboxamide (AB-FUBINACA) identified as designer drugs in illegal products. Forensic Toxicol. 2013, 31, 93.
19. H. Chung, H. Choi, S. Heo, E. Kim, J. Lee. Synthetic cannabinoids abused in South Korea: drug identifications by the national forensic service from 2009 to June 2013. Forensic Toxicol. 2014, 32, 82.
20. N. Uchiyama, Y. Shimokawa, S. Matsuda, M. Kawamura, R. Kikura-Hanajiri, Y. Goda. Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products. Forensic Toxicol. 2014, 32, 105.
21. R. Kikura-Hanajiri, N. Uchiyama, M. Kawamura, Y. Goda. 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. 2014, 6, 832.
22. N. Uchiyama, Y. Shimokawa, M. Kawamura, R. Kikura-Hanajiri, T. Hakamatsuka. Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products. Forensic Toxicol. 2014, 32, 266.
23. L. M. Huppertz, S. Kneisel, V. Auwärter, J. Kempf. A comprehensive library-based, automated screening procedure for 46 synthetic cannabinoids in serum employing liquid chromatography quadrupole ion trap mass spectrometry with high-temperature electrospray ionization. J. Mass Spectrom. 2014, 49, 117.
24. N. Uchiyama, Y. Shimokawa, R. Kikura-Hanajiri, Y. Demizu, Y. Goda, T. Hakamatsuka. A synthetic cannabinoid FDU-NNEI, two 2H-indazole isomers of synthetic cannabinoids AB-CHMINACA and NNEI indazole analog (MN-18), a phenethylamine derivative N–OH-EDMA, and a cathinone derivative dimethoxy-α-PHP, newly identified in illegal products. Forensic Toxicol. 2015, 33, 244.
25. A. Wurita, K. Hasegawa, K. Minakata, K. Gonmori, H. Nozawa, I. Yamagishi, K. Watanabe, O. Suzuki. Identification and quantitation of 5-fluoro-ADB-PINACA and MAB-CHMINACA in dubious herbal products. Forensic Toxicol. 2015, 33, 213.
26. N. Uchiyama, K. Asakawa, R. Kikura-Hanajiri, T. Tsutsumi, T. Hakamatsuka. A new pyrazole-carboxamide type synthetic cannabinoid AB-CHFUPYCA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide] identified in illegal products. Forensic Toxicol. 2015, 33, 367.
27. G. McLaughlin, N. Morris, P.V. Kavanagh, J.D. Power, B. Twamley, J. O'Brien, B. Talbot, G. Dowling, S.D. Brandt. The synthesis and characterization of the ‘research chemical’ N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide (3,5-AB-CHMFUPPYCA) and differentiation from its 5,3-regioisomer. Drug Test. Anal. 2015. DOI:http://dx.doi.org/10.1002/dta.1864
28. 13C NMR shifts - a case study. Drug Test. Anal. 2015, DOI:http://dx.doi.org/10.1002/dta.1820
29. F. Westphal, F. D. Sönnichsen, S. Knecht, V. Auwärter, L. Huppertz. Two thiazolylindoles and a benzimidazole: novel compounds on the designer drug market with potential cannabinoid receptor activity. Forensic Sci. Int. 2015, 249, 133.
30. V. Shevyrin, V. Melkozerov, A. Nevero, O. Eltsov, Y. Shafran, Y. Morzherin, A. T. Lebedev. Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group. Anal. Bioanal. Chem. 2015, 407, 6301.
31. Z. Qian, Z. Hua, C. Liu, W. Jia. Four types of cannabimimetic indazole and indole derivatives, ADB-BINACA, AB-FUBICA, ADB-FUBICA, and AB-BICA, identified as new psychoactive substances. Forensic Toxicol. 2016, 34, 133.
32. C. Liu, W. Jia, Z. Qian, T. Li, Z. Hua. Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe. Drug Test. Anal. 2016, DOI http://dx.doi.org/10.1002/dat.1955
33. E. Pretsch, P. Bühlmann, C. Affolter. Structure Determination of Organic Compounds: Tables of Spectral Data, Springer, Berlin 2004.