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Chemical compound
FUBIMINA
Legal status
(1-(5-fluoropentyl)-1H -benzo[d ]imidazol-2-yl)(naphthalen-1-yl)methanone
CAS Number
PubChem
CID
ChemSpider
UNII
Formula C 23 H 21 F N 2 O
Molar mass 360.432 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 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]
See also
References
^
"FUBIMINA" . Cayman Chemical. Retrieved 22 June 2015 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
Phytocannabinoids (
comparison )
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