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 Testing and Analysis

Volumn 8, Issue 9, 2016, Pages 920-929

  McLaughlin, Gavin ^a,b   Morris, Noreen ^a   Kavanagh, Pierce V ^b   Power, John D ^b,c   Twamley, Brendan ^d   O'Brien, John ^d   Talbot, Brian ^d   Dowling, Geraldine ^e   Brandt, Simon D ^f  

^a Athletic Rehabilitation Therapy Ireland   (Ireland)

^b ST JAMES S HOSPITAL   (Ireland)

^c Forensic Science Laboratory Dulin Ireland   (Ireland)

^d TRINITY COLLEGE DUBLIN   (Ireland)

^e Food and the Marine   (Ireland)

^f LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

AB CHMFUPPYCA isomers; new psychoactive substances; pyrazole carboxamide derivatives; synthetic cannabinoids

Indexed keywords

1H-PYRAZOLE; AB-CHMFUPPYCA ISOMER; ANALYTICAL CHARACTERIZATION; CARBOXAMIDES; NEW PSYCHOACTIVE SUBSTANCE; PYRAZOLE-CARBOXAMIDE DERIVATIVE; PYRAZOLES; REGIOISOMERS; SYNTHESIS AND CHARACTERIZATIONS; SYNTHETIC CANNABINOID;

ISOMERS;

CANNABINOID; PSYCHOTROPIC AGENT; PYRAZOLE; PYRAZOLE DERIVATIVE; PYRAZOLE-5-CARBOXAMIDE; STREET DRUG;

CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; INTERNET; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CANNABINOIDS; CHROMATOGRAPHY, LIQUID; CRYSTALLOGRAPHY, X-RAY; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; INTERNET; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PSYCHOTROPIC DRUGS; PYRAZOLES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STREET DRUGS;

EID: 85028259061     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1864     Document Type: Article

References (31)

1. S.D. Brandt, L.A. King, M. Evans-Brown. The new drug phenomenon. Drug Test. Anal. 2014, 6, 587.
2. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). New psychoactive substances in Europe. An update from the EU Early Warning System (March 2015). Lisbon. 2015. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_235958_EN_TD0415135ENN.pdf [13 June 2015].
3. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). European Drug Report. Trends and Developments. Lisbon. 2015. Available at: http://www.emcdda.europa.eu/attachements.cfm/att_239505_EN_TDAT15001ENN.pdf [13 June 2015].
4. 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.
5. 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.
6. 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.
7. 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.
8. G. Behonick, K.G. Shanks, D.J. Firchau, G. Mathur, C.F. Lynch, M. Nashelsky, D.J. Jaskierny, C. Meroueh. Four postmortem case reports with quantitative detection of the synthetic cannabinoid, 5F-PB-22. J. Anal. Toxicol. 2014, 38, 559.
9. T. Takayama, M. Suzuki, K. Todoroki, K. Inoue, J.Z. Min, R. Kikura-Hanajiri, Y. Goda, T. Toyo'oka. UPLC/ESI-MS/MS-based determination of metabolism of several new illicit drugs, ADB-FUBINACA, AB-FUBINACA, AB-PINACA, QUPIC, 5 F-QUPIC and α-PVT, by human liver microsome. Forensic Toxicol. 2014, 28, 831.
10. R. Thomsen, L.M. Nielsen, N.B. Holm, H.B. Rasmussen, K. Linnet. Synthetic cannabimimetic agents metabolized by carboxylesterases. Drug Test. Anal. 2014, 7, 565.
11. 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.
12. M.S. Castaneto, A. Wohlfarth, S. Pang, M. Zhu, K.B. Scheidweiler, R. Kronstrand, M.A. Huestis. Identification of AB-FUBINACA metabolites in human hepatocytes and urine using high-resolution mass spectrometry. Forensic Toxicol. 2015, 33, 295.
13. C. Erratico, N. Negreira, H. Norouzizadeh, A. Covaci, H. Neels, K. Maudens, A.L. van Nuijs. In vitro and in vivo human metabolism of the synthetic cannabinoid AB-CHMINACA. Drug Test. Anal. 2015. DOI:10.1002/dta.1796.
14. 9-Tetrahydrocannabinol-like effects of novel synthetic cannabinoids found on the gray market. Behav. Pharmacol. 2015, 26, 460.
15. K. Hasegawa, A. Wurita, K. Minakata, K. Gonmori, H. Nozawa, I. Yamagishi, K. Watanabe, O. Suzuki. Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB, and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of adipose tissue for detection of the drugs in unchanged forms. Forensic Toxicol. 2015, 33, 45.
16. K. Hasegawa, A. Wurita, K. Minakata, K. Gonmori, I. Yamagishi, H. Nozawa, K. Watanabe, O. Suzuki. Identification and quantitation of 5-fluoro-ADB, one of the most dangerous synthetic cannabinoids, in the stomach contents and solid tissues of a human cadaver and in some herbal products. Forensic Toxicol. 2015, 33, 112.
17. M.D. Schwartz, J. Trecki, L.A. Edison, A.R. Steck, J.K. Arnold, R.R. Gerona. A common source outbreak of severe delirium associated with exposure to the novel synthetic cannabinoid ADB-PINACA. J. Emerg. Med. 2015, 48, 573.
18. 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.
19. A. Wohlfarth, M.S. Castaneto, M. Zhu, S. Pang, K.B. Scheidweiler, R. Kronstrand, M.A. Huestis. Pentylindole/pentylindazole synthetic cannabinoids and their 5-fluoro analogs produce different primary metabolites: metabolite profiling for AB-PINACA and 5F-AB-PINACA. AAPS J. 2015, 17, 660.
20. 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.
21. Drug Enforcement Administration, Department of Justice. Schedules of controlled substances: temporary placement of four synthetic cannabinoids into Schedule I. Final order. Fed. Regist. 2014, 79, 7577.
22. Drug Enforcement Administration, Department of Justice. Schedules of controlled substances: temporary placement of three synthetic cannabinoids into Schedule I. Final order. Fed. Regist. 2015, 80, 5042.
23. 13C NMR shifts - a case study. Drug Test. Anal. 2015. DOI:10.1002/dta.1820.
24. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). Early-Warning-System on New Drugs. AB-CHMFUPPYCA. EMCDDA database on new drugs (EDND). 2015. Restricted access.
25. 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.
26. 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.
27. L.A. King. Legal controls on cannabimimetics: an international dilemma? Drug Test. Anal. 2014, 6, 80.
28. 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.
29. I.P. Buchler, M.J. Hayes, S.G. Hedge, S.L. Hockerman, D.E. Jones, S.W. Kortum, J.G. Rico, R.E. Tenbrink, K.K. Wu. Indazole derivatives. Pfizer Inc., USA. Patent No. WO2009106982A1, 2009.
30. I.P. Buchler, M.J. Hayes, S.G. Hegde, S.L. Hockerman, D.E. Jones, S.W. Kortum, J.G. Rico, R.E. Tenbrink, K.K. Wu. Indazole derivatives. Pfizer Inc., USA. Patent No. WO2009106980A2, 2009.
31. European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). Early-Warning-System on New Drugs. 5F-AB-FUPPYCA. EMCDDA database on new drugs (EDND). 2015. Restricted access.