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
- 1.1k Downloads
Two new types of synthetic cannabinoids, an AM-2201 benzimidazole analog (FUBIMINA, 1) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM, 2), and three newly emerged phenethylamine derivatives, 25B-NBOMe (3), 2C-N-NBOMe (4), and a 25H-NBOMe 3,4,5-trimethoxybenzyl analog (5), were detected in illegal products distributed in Japan. The identification was based on liquid chromatography–mass spectrometry (LC–MS) and gas chromatography–mass spectrometry (GC–MS), high-resolution MS, and nuclear magnetic resonance analyses. Different from the representative synthetic cannabinoids, such as JWH-018, which have a naphthoylindole moiety, compounds 1 and 2 were completely new types of synthetic cannabinoids; compound 1 had a benzimidazole group in place of an indole group, and compound 2 had a 4-methylpiperazine group in place of the naphthyl group. Compounds 3 and 4 were N-o-methoxybenzyl derivatives of 2,5-dimethoxyphenethylamines (25-NBOMe series), which had been previously detected in European countries, but have newly emerged in Japan. Compound 5 had an N-trimethoxybenzyl group in place of an N-o-methoxybenzyl group. Data on the chemistry and pharmacology of compounds 1, 2, and 5 have never been reported to our knowledge.
KeywordsAM-2201 benzimidazole analog (FUBIMINA) (4-Methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM) 25H-NBOMe 3,4,5-trimethoxybenzyl analog 25B-NBOMe 2C-N-NBOMe Synthetic cannabinoid
Part of this work was supported by a Health and Labor Sciences Research Grant from the Ministry of Health, Labour, and Welfare, Japan.
Conflict of interest
There are no financial or other relations that could lead to a conflict of interest.
- 1.UNODC (2013) Global SMART update 2013—vol 10, September 2013. http://www.unodc.org/documents/scientific/Global_SMART_Update_10_web.pdf. Accessed Sept 2013
- 2.UNODC (2013) The challenge of new psychoactive substances. A report from the global SMART programme, March 2013. http://www.unodc.org/documents/scientific/NPS_2013_SMART.pdf. Accessed Sept 2013
- 3.EMCDDA (2013) EMCDDA/Europol, 2005/387/JHA, EMCDDA-Europol 2012 annual report on the implementation of council decision, Lisbon, May 2013. http://www.emcdda.europa.eu/publications/implementation-reports/2012. Accessed May 2013
- 6.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 31:223–240CrossRefGoogle Scholar
- 7.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 31:93–100CrossRefGoogle Scholar
- 8.Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013) Identification of two new-type designer drugs, a piperazine derivative MT-45 (I-C6) and a synthetic peptide Noopept (GVS-111), with a synthetic cannabinoid A-834735, a cathinone derivative 4-methoxy-α-PVP and a phenethylamine derivative 4-methylbuphedrine from illegal products. Forensic Toxicol. doi: 10.1007/s11419-013-0194-5 Google Scholar
- 9.Kikura-Hanajiri R, Uchiyama N, Kawamura M, Goda Y (2013) 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. doi: 10.1002/dta.1584
- 11.Lopyrev VA, Larina LI, Vakul’skaya TI, Shibanova EF, Titova IA, Voronkov MG, Liepins E (1982) Investigation of benzimidazoles. III. Transmission of the substituent effects in 2-substituted 1-methylbenzimidazoles studied by carbon-13 nuclear magnetic resonance. Org Magn Reson 20:212–216CrossRefGoogle Scholar
- 12.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 30:114–125CrossRefGoogle Scholar
- 13.Moir EM, Yoshiizumi K, Cairns J, Cowley P, Ferguson M, Jeremiah F, Kiyoi T, Morphy R, Tierney J, Wishart G, York M, Baker J, Cottney JE, Houghton AK, McPhail P, Osprey A, Walker G, Adam JM (2010) Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists. Med Chem Commun 1:54–60CrossRefGoogle Scholar