FUBIMINA

{{Short description|Chemical compound}}

{{technical|date=June 2015}}

{{Drugbox

| IUPAC_name = (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone

| image = FUBIMINA_structure.png

| image_class = skin-invert-image

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = Class B

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 1984789-90-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = U96GD9R3UZ

| ATC_prefix =

| ATC_suffix =

| PubChem = 124519316

| ChemSpiderID = 30646758

| smiles = O=C(C1=NC2=C(C=CC=C2)N1CCCCCF)C3=CC=CC4=CC=CC=C43

| StdInChI = 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

| StdInChIKey = KUESSZMROAFKQJ-UHFFFAOYSA-N

| C=23 | H=21 | F=1 | N=2 | O=1

}}

FUBIMINA (also known as BIM-2201, BZ-2201 and FTHJ) is a synthetic cannabinoid that is the benzimidazole analog of AM-2201{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15202 | title=FUBIMINA | publisher=Cayman Chemical | access-date=22 June 2015}} and has been used as an active ingredient in synthetic cannabis products.{{cite journal | vauthors = Diao X, Scheidweiler KB, Wohlfarth A, Zhu M, Pang S, Huestis MA | title = Strategies to distinguish new synthetic cannabinoid FUBIMINA (BIM-2201) intake from its isomer THJ-2201: metabolism of FUBIMINA in human hepatocytes | journal = Forensic Toxicology | volume = 34 | issue = 2 | pages = 256–267 | date = 2016 | pmid = 27547265 | pmc = 4971051 | doi = 10.1007/s11419-016-0312-2 }} It was first identified in Japan in 2013, alongside MEPIRAPIM.{{cite journal | title=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 |vauthors=Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | journal=Forensic Toxicology | year=2014 | volume=32 | issue=1 | pages=105–115 | doi=10.1007/s11419-013-0217-2|s2cid=32599561 }}

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.{{cite journal | vauthors = Wiley JL, Marusich JA, Lefever TW, Antonazzo KR, Wallgren MT, Cortes RA, Patel PR, Grabenauer M, Moore KN, Thomas BF | display-authors = 6 | title = AB-CHMINACA, AB-PINACA, and FUBIMINA: Affinity and Potency of Novel Synthetic Cannabinoids in Producing Δ9-Tetrahydrocannabinol-Like Effects in Mice | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 354 | issue = 3 | pages = 328–339 | date = September 2015 | pmid = 26105953 | pmc = 4538877 | doi = 10.1124/jpet.115.225326 }}

Related benzimidazole derivatives have been reported to be highly selective agonists for the CB₂ receptor.{{cite journal | vauthors = Pagé D, Balaux E, Boisvert L, Liu Z, Milburn C, Tremblay M, Wei Z, Woo S, Luo X, Cheng YX, Yang H, Srivastava S, Zhou F, Brown W, Tomaszewski M, Walpole C, Hodzic L, St-Onge S, Godbout C, Salois D, Payza K | display-authors = 6 | title = Novel benzimidazole derivatives as selective CB2 agonists | journal = Bioorganic & Medicinal Chemistry Letters | volume = 18 | issue = 13 | pages = 3695–3700 | date = July 2008 | pmid = 18522867 | doi = 10.1016/j.bmcl.2008.05.073 }}