FUBIMINA

FUBIMINA

Systematic (IUPAC) name
(1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone
Legal status
Legal status	CA: Schedule II
Identifiers
ChemSpider	30646758
Chemical data
Formula	C23H21FN2O
Molar mass	360.4 g/mol
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 (Ki = 23.45 nM), with 12x selectivity over CB₁ (Ki = 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]

See also

• AM-694
• AM-1235
• AM-2232
• AM-2233
• BIM-018
• JWH-018
• List of AM cannabinoids
• List of JWH cannabinoids
• THJ-2201

References

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.
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, and 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.