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FUBIMINA

From Wikipedia, the free encyclopedia
Chemical compound
This articlemay be too technical for most readers to understand. Pleasehelp improve it tomake it understandable to non-experts, without removing the technical details.(June 2015) (Learn how and when to remove this message)
Pharmaceutical compound
FUBIMINA
Legal status
Legal status
Identifiers
  • (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC23H21FN2O
Molar mass360.432 g·mol−1
3D model (JSmol)
  • O=C(C1=NC2=C(C=CC=C2)N1CCCCCF)C3=CC=CC4=CC=CC=C43
  • 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 asBIM-2201,BZ-2201 andFTHJ) is a syntheticcannabinoid that is thebenzimidazoleanalog ofAM-2201[1] and has been used as an active ingredient insynthetic cannabis products.[2] It was first identified in Japan in 2013, alongsideMEPIRAPIM.[3]

FUBIMINA acts as a reasonably potentagonist for theCB2 receptor (Ki = 23.45 nM), with 12x selectivity overCB1 (Ki = 296.1 nM), and does not fully substitute forΔ9-THC in rat discrimination studies.[4]

Related benzimidazole derivatives have been reported to be highly selectiveagonists for theCB2 receptor.[5]

See also

[edit]

References

[edit]
  1. ^"FUBIMINA". Cayman Chemical. Retrieved22 June 2015.
  2. ^Diao X, Scheidweiler KB, Wohlfarth A, Zhu M, Pang S, Huestis MA (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.
  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. ^Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, et al. (September 2015)."AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice".The Journal of Pharmacology and Experimental Therapeutics.354 (3):328–339.doi:10.1124/jpet.115.225326.PMC 4538877.PMID 26105953.
  5. ^Pagé D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, et al. (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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