FUBIMINA

FUBIMINA
Legal status
Legal status	CA: Schedule II;
Identifiers
	IUPAC name (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone;
ChemSpider	30646758;
Chemical and physical data
Formula	C23H21FN2O
Molar mass	360.4 g/mol
3D model (Jmol)	Interactive image;
	SMILES O=C(C1=NC2=C(C=CC=C2)N1CCCCCF)C3=CC=CC4=CC=CC=C43 ;
	InChI InChI=1S/C23H21FN2O/c24-15-6-1-7-16-26-21-14-5-4-13-20(21)25-23(26)22(27)19-12-8-10-17-9-2-3-11-18(17)19/h2-5,8-14H,1,6-7,15-16H2 ; Key:KUESSZMROAFKQJ-UHFFFAOYSA-N ;

FUBIMINA (also known as BIM-2201, BZ-2201 and FTHJ) is a synthetic cannabinoid that is the benzimidazole analog of AM-2201^[1] and has been used as an active ingredient in synthetic cannabis products.^[2] It was first identified in Japan in 2013, alongside MEPIRAPIM.^[3]

FUBIMINA acts as a reasonably potent agonist for the CB₂ receptor (K_i = 23.45 nM), with 12x selectivity over CB₁ (K_i = 296.1 nM), and does not fully substitute for Δ⁹-THC in rat discrimination studies.^[4]

Related benzimidazole derivatives have been reported to be highly selective agonists for the CB₂ receptor.^[5]

References[edit]

^ "FUBIMINA". Cayman Chemical. Retrieved 22 June 2015.
^ Xingxing Diao; Karl B. Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A. Huestis (2016). "Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes". Forensic Toxicology. doi:10.1007/s11419-016-0312-2.
^ 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 Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2.
^ Jenny L Wiley; Julie A Marusich; Timothy W Lefever; Kateland R Antonazzo; Michael T Wallgren; Ricardo A Cortes; Purvi R Patel; Megan Grabenauer; Katherine N Moore; Brian F Thomas (June 2015). "AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ⁹-Tetrahydrocannabinol-Like Effects in Mice". Journal of Pharmacology and Experimental Therapeutics. 354: 328–39. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.
^ Daniel Pagé; Elise Balaux; Luc Boisvert; Ziping Liu; Claire Milburn; Maxime Tremblay; Zhongyong Wei; Simon Woo; Xuehong Luo; Yun-Xing Cheng; Hua Yang; Sanjay Srivastava; Fei Zhou; William Brown; Miroslaw Tomaszewski; Christopher Walpole; Leila Hodzic; Stéphane St-Onge; Claude Godbout; Dominic Salois; Keymal Payza (July 2008). "Novel benzimidazole derivatives as selective CB₂ agonists". Bioorganic & Medicinal Chemistry Letters. 18 (13): 3695–3700. doi:10.1016/j.bmcl.2008.05.073. PMID 18522867.

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[1] "FUBIMINA". Cayman Chemical. Retrieved 22 June 2015.

[2] Xingxing Diao; Karl B. Scheidweiler; Ariane Wohlfarth; Mingshe Zhu; Shaokun Pang; Marilyn A. Huestis (2016). "Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes". Forensic Toxicology. doi:10.1007/s11419-016-0312-2.

[Uchiyama_2014-3] 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 Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2.

[4] Jenny L Wiley; Julie A Marusich; Timothy W Lefever; Kateland R Antonazzo; Michael T Wallgren; Ricardo A Cortes; Purvi R Patel; Megan Grabenauer; Katherine N Moore; Brian F Thomas (June 2015). "AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ⁹-Tetrahydrocannabinol-Like Effects in Mice". Journal of Pharmacology and Experimental Therapeutics. 354: 328–39. doi:10.1124/jpet.115.225326. PMC 4538877. PMID 26105953.

[5] Daniel Pagé; Elise Balaux; Luc Boisvert; Ziping Liu; Claire Milburn; Maxime Tremblay; Zhongyong Wei; Simon Woo; Xuehong Luo; Yun-Xing Cheng; Hua Yang; Sanjay Srivastava; Fei Zhou; William Brown; Miroslaw Tomaszewski; Christopher Walpole; Leila Hodzic; Stéphane St-Onge; Claude Godbout; Dominic Salois; Keymal Payza (July 2008). "Novel benzimidazole derivatives as selective CB₂ agonists". Bioorganic & Medicinal Chemistry Letters. 18 (13): 3695–3700. doi:10.1016/j.bmcl.2008.05.073. PMID 18522867.

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[5]

FUBIMINA

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Legal status

Legal status	CA: Schedule II
Identifiers
IUPAC name (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone
ChemSpider	30646758
Chemical and physical data
Formula	C₂₃H₂₁FN₂O
Molar mass	360.4 g/mol
3D model (Jmol)	Interactive image
SMILES O=C(C1=NC2=C(C=CC=C2)N1CCCCCF)C3=CC=CC4=CC=CC=C43
InChI InChI=1S/C23H21FN2O/c24-15-6-1-7-16-26-21-14-5-4-13-20(21)25-23(26)22(27)19-12-8-10-17-9-2-3-11-18(17)19/h2-5,8-14H,1,6-7,15-16H2 Key:KUESSZMROAFKQJ-UHFFFAOYSA-N