FUBIMINA

FUBIMINA
Legal status
Legal status	CA: Schedule II ; DE: NpSG (Industrial and scientific use only) ; UK: Class B ;
Identifiers
	IUPAC name (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone;
CAS Number	1984789-90-3 ;
PubChem CID	124519316;
ChemSpider	30646758;
UNII	U96GD9R3UZ;
Chemical and physical data
Formula	C23H21FN2O
Molar mass	360.432 g·mol−1
3D model (JSmol)	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

"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. 34 (2): 256–267. doi:10.1007/s11419-016-0312-2. PMC 4971051. PMID 27547265.
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. S2CID 32599561.
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 (3): 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. 34 (2): 256–267. doi:10.1007/s11419-016-0312-2. PMC 4971051. PMID 27547265.

[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. S2CID 32599561.

[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 (3): 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.

FUBIMINA

See also

References