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Erschienen in: Forensic Toxicology 2/2015

01.07.2015 | Original Article

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

verfasst von: Nahoko Uchiyama, Kazuhiro Asakawa, Ruri Kikura-Hanajiri, Taizo Tsutsumi, Takashi Hakamatsuka

Erschienen in: Forensic Toxicology | Ausgabe 2/2015

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Abstract

A new pyrazole-carboxamide type synthetic cannabinoid, AB-CHFUPYCA (1), was detected in illegal herbal products by our ongoing survey in Japan. The structure of 1 was identified by gas chromatography–mass spectrometry (GC–MS), liquid chromatography–mass spectrometry (LC–MS), liquid chromatography–high-resolution-mass spectrometry (LC–HR-MS) and nuclear magnetic resonance (NMR) analyses. Compound 1 showed a molecular weight of 400, and accurate mass measurement using LC–HR-MS revealed its molecular formula to be C22H29N4O2F. The MS and NMR spectrometric data revealed that the structure of 1 was N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(cyclohexylmethyl)-3-(4-fluorophenyl)-1H-pyrazole-5-carboxamide. Compound 1, which is a new type of synthetic cannabinoid, has a 3-(4-fluorophenyl)-1H-pyrazole group in place of a 1H-indazole group of AB-CHMINACA. To our knowledge, data on the chemistry and pharmacology of compound 1 have never been reported, and we therefore named compound 1 “AB-CHFUPYCA.”
Literatur
1.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
2.
Zurück zum Zitat 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 CrossRef 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 CrossRef
3.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
4.
Zurück zum Zitat 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 CrossRef 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 CrossRef
5.
Zurück zum Zitat Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1 H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1 H-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 CrossRef Uchiyama N, Kawamura M, Kikura-Hanajiri R, Goda Y (2012) Identification of two new-type synthetic cannabinoids, N-(1-adamantyl)-1-pentyl-1 H-indole-3-carboxamide (APICA) and N-(1-adamantyl)-1-pentyl-1 H-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 CrossRef
6.
Zurück zum Zitat 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-1 H-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 CrossRef 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-1 H-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 CrossRef
7.
Zurück zum Zitat 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 CrossRef 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 CrossRef
8.
Zurück zum Zitat 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-1 H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1 H-indazole-3-carboxamide (AB-FUBINACA), identified as designer drugs in illegal products. Forensic Toxicol 31:93–100 CrossRef 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-1 H-indazole-3-carboxamide (AB-PINACA) and N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1 H-indazole-3-carboxamide (AB-FUBINACA), identified as designer drugs in illegal products. Forensic Toxicol 31:93–100 CrossRef
10.
Zurück zum Zitat Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) A synthetic cannabinoid FDU-NNEI, two 2 H-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 Uchiyama N, Shimokawa Y, Kikura-Hanajiri R, Demizu Y, Goda Y, Hakamatsuka T (2015) A synthetic cannabinoid FDU-NNEI, two 2 H-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.
Zurück zum Zitat 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 CrossRef 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 CrossRef
12.
Zurück zum Zitat 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 CrossRef 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 CrossRef
13.
Zurück zum Zitat 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 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.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
15.
Zurück zum Zitat 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 CrossRef 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 CrossRef
16.
Zurück zum Zitat 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 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.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
18.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
19.
Zurück zum Zitat 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) PubMedCrossRef 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) PubMedCrossRef
20.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
21.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
22.
Zurück zum Zitat 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 PubMedCrossRef 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 PubMedCrossRef
23.
Zurück zum Zitat 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 CrossRef 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 CrossRef
Metadaten
Titel
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
verfasst von
Nahoko Uchiyama
Kazuhiro Asakawa
Ruri Kikura-Hanajiri
Taizo Tsutsumi
Takashi Hakamatsuka
Publikationsdatum
01.07.2015
Verlag
Springer Japan
Erschienen in
Forensic Toxicology / Ausgabe 2/2015
Print ISSN: 1860-8965
Elektronische ISSN: 1860-8973
DOI
https://doi.org/10.1007/s11419-015-0283-8

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