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 Toxicology

Volumn 33, Issue 2, 2015, Pages 367-373

  Uchiyama, Nahoko ^a   Asakawa, Kazuhiro ^b   Kikura Hanajiri, Ruri ^a   Tsutsumi, Taizo ^b   Hakamatsuka, Takashi ^a  

^a NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^b Pharmaceutical and Environmental Sciences Center   (Japan)

Author keywords

AB CHFUPYCA N (1 amino 3 methyl 1 oxobutan 2 yl) 1 (cyclohexylmethyl) 3 (4 fluorophenyl) 1H pyrazole 5 carboxamide ; Drug of abuse; Illegal product; New psychoactive substance; Pyrazole carboxamide derivative; Synthetic cannabinoid

Indexed keywords

CANNABINOID DERIVATIVE; ILLICIT DRUG; UNCLASSIFIED DRUG; [N (1 AMINO 3 METHYL 1 OXOBUTAN 2 YL) 1 (CYCLOHEXYLMETHYL) 3 (4 FLUOROPHENYL) 1H PYRAZOLE 5 CARBOXAMIDE];

ACCURACY; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; INTERMETHOD COMPARISON; JAPAN; LIQUID CHROMATOGRAPHY HIGH RESOLUTION MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY MASS SPECTROMETRY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; STRUCTURE ANALYSIS;

EID: 84937526290     PISSN: 18608965     EISSN: 18608973     Source Type: Journal    
DOI: 10.1007/s11419-015-0283-8     Document Type: Article

References (23)

1. 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
2. Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) Changes in the prevalence of synthetic cannabinoids and cathinone derivatives in Japan until early 2012. Forensic Toxicol 31:44–53
3. 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
4. Uchiyama N, Kikura-Hanajiri R, Kawahara N, Goda Y (2009) Identification of a cannabimimetic indole as a designer drug in a herbal product. Forensic Toxicol 27:61–66
5. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) 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 30:114–125
6. Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014) 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 32:105–117
7. Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) 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 31:223–240
8. Uchiyama N, Matsuda S, Wakana D, Kikura-Hanajiri R, Goda Y (2013) 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 31:93–100
9. EMCDDA (2015) New psychoactive substances in Europe. An update from the EU Early Warning System, March 2015. http://www.emcdda.europa.eu/attachements.cfm/att_235958_EN_TD0415135ENN.pdf. Accessed May 2015
10. Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) 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. doi:10.1007/s11419-015-0268-7
11. Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) 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 33:45–53
12. Hasegawa K, Wurita A, Minakata K, Gonmori K, Yamagishi I, Nozawa H, Watanabe K, Suzuki O (2015) 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 33:112–121
13. Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (2015) Postmortem distribution of MAB-CHMINACA in body fluids and solid tissues of a human cadaver. Forensic Toxicol. doi:10.1007/s11419-015-0272-y
14. Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) URB-754: a new class of designer drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci Int 227:21–32
15. Katritzky AR, Ramsden CA, Joule JA, Zhdankin VV (2010) Structure of five-membered rings with two or more heteroatoms. In: Handbook of heterocyclic chemistry, 3rd edn. Elsevier, Amsterdam, pp 139–207
16. Pinto DCGA, Santos CMM, Silva AMS (2007) Advanced NMR techniques for structural characterization of heterocyclic structures. In: Pinho e Melo TMVD (ed) Recent research developments in heterocyclic chemistry. Research Signpost, Kerala, pp 397–475
17. Rinaldi-Carmona M, Barth F, Héaulme M, Shire D, Calandra B, Congy C, Martinez S, Maruani J, Néliat G, Caput D, Ferrara P, Soubrié P, Brelière JC, Le Fur G (1994) SR 141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett 350:240–244
18. Rinaldi-Carmona M, Barth F, Héaulme M, Alonso R, Shire D, Congy C, Soubrié P, Brelière JC, Le Fur G (1995) Biochemical and pharmacological characterisation of SR 141716A, the first potent and selective brain cannabinoid receptor antagonist. Life Sci 56:1941–1947
19. Christensen R, Kristensen PK, Bartels EM, Bliddal H, Astrup A (2007) Efficacy and safety of the weight-loss drug rimonabant: a meta-analysis of randomised trials. Lancet 370:1706–1713 (1671–1672 comment)
20. Lan R, Liu Q, Fan P, Lin S, Fernando SR, McCallion D, Pertwee R, Makriyannis A (1999) Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J Med Chem 42:769–776
21. Lan R, Gatley J, Lu Q, Fan P, Fernando SR, Volkow ND, Pertwee R, Makriyannis A (1999) Design and synthesis of the CB1 selective cannabinoid antagonist AM281: a potential human SPECT ligand. AAPS PharmSci 1(2):E4
22. Ernst L, Krüger K, Lindigkeit R, Schiebel HM, Beuerle T (2012) Synthetic cannabinoids in ‘‘spice-like’’ herbal blends: first appearance of JWH-307 and recurrence of JWH-018 on the German market. Forensic Sci Int 222:216–222
23. Huffman JW (2009) Cannabimimetic indoles, pyrroles, and indenes: structure-activity relationships and receptor interactions. In: Reggio PH (ed) The cannabinoid receptors. Humana Press, New York, pp 49–94