FUBIMINA

FUBIMINA
Legal status

Legal status	CA: Schedule II
Identifiers
IUPAC name (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone
ChemSpider	30646758
Chemical and physical data
Formula	C₂₃H₂₁FN₂O
Molar mass	360.4 g/mol
3D model (Jmol)	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. doi:10.1007/s11419-016-0312-2.
↑ 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.
↑ 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: 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.

Cannabinoids

Phytocannabinoids

Active metabolites: 8,11-DiOH-THC
11-COOH-THC
11-OH-THC

Endocannabinoids

Synthetic
cannabinoids

Classical cannabinoids (dibenzopyrans)	A-40174 A-41988 A-42574 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-926 AM-938 AM-2389 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol (HU-211) DMHP Dronabinol HHC HU-210 HU-243 JWH-051 JWH-133 JWH-139 JWH-161 JWH-229 JWH-359 KM-233 L-759,633 L-759,656 Levonantradol (CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 O-2365 O-2372 O-2373 O-2383 O-2426 O-2484 O-2545 O-2694 O-2715 O-2716 O-3223 O-3226 Parahexyl Pirnabine THC-O-acetate THC-O-phosphate

Non-classical cannabinoids	Cannabicyclohexanol CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 HU-308 HU-320 HU-331 HU-336 HU-345 HU-446 HU-465 HU-910 HUF-101 HUF-102 HUF-103 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 SPA-229 Tinabinol 2-Isopropyl-5-methyl-1- (2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

Benzoylindoles	1-Butyl-3-(2-methoxybenzoyl)indole 1-Butyl-3-(4-methoxybenzoyl)indole 1-Pentyl-3-(2-methoxybenzoyl)indole AM-630 AM-679 AM-694 AM-1241 AM-2233 GW-405,833 (L-768,242) Pravadoline RCS-4 WIN 54,461

Naphthoylindoles	AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 JWH-007 JWH-015 JWH-018 JWH-019 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-164 JWH-182 JWH-193 JWH-198 JWH-200 JWH-210 JWH-398 JWH-424 MAM-1220 MAM-2201 NE-CHMIMO

Naphthoylindazoles	THJ-018 THJ-2201

Pyrrolobenzoxazines	WIN 55,212-2

Naphthylmethylindoles	JWH-175 JWH-176 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199

Phenylacetylindoles	Cannabipiperidiethanone JWH-167 JWH-203 JWH-249 JWH-250 JWH-251 JWH-302 RCS-8

Indole-3-carboxamides	5F-ADBICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA CUMYL-BICA CUMYL-PICA CUMYL-5F-PICA FDU-NNE1 MDMB-CHMICA MMB-2201 MN-25 (UR-12) NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135

Indole-3-carboxylates	5F-PB-22 FDU-PB-22 FUB-PB-22 QUCHIC (BB-22) QUPIC (PB-22) NM-2201

Tetramethylcyclo- propanoylindoles	5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12

Indazole-3- carboxamides	5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-EMB-PINACA AB-CHMINACA AB-FUBINACA AB-FUBINACA 2-fluorobenzyl isomer AB-PINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADAMANTYL-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA CUMYL-PINACA CUMYL-THPINACA EMB-FUBINACA FUB-APINACA MDMB-FUBINACA MDMB-CHMINACA MN-18 PX-2 PX-3

Tetramethylcyclo- propanoylindazoles	FAB-144

Naphthoylpyrroles	JWH-030 JWH-147 JWH-307 JWH-369 JWH-370

Eicosanoids	AM-883 AM-1346 ACEA ACPA Methanandamide (AM-356) O-585 O-689 O-1812 O-1860 O-1861

Pyrazolecarboxamides	5F-AB-FUPPYCA AB-CHFUPYCA AB-CHMFUPPYCA

Others	4-HTMPIPO 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole A-836,339 A-955,840 Abnormal cannabidiol AB-001 BzODZ-EPyr AM-1248 AM-1714 AZ-11713908 BAY 38-7271 BAY 59-3074 BIM-018 CB-13 CB-86 CBS-0550 FUBIMINA GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 MEPIRAPIM NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 PF-03550096 PSB-SB-1202 PTI-1 PTI-2 QMPSB S-444,823 SER-601 Tedalinab URB-447 VSN-16 WIN 56,098

Allosteric CBR ligands

Org 27569
Org 27759
Org 29647
RTI-371
Pregnenolone

Endocannabinoid
enhancers
(inactivation inhibitors)

Anticannabinoids
(antagonists/inverse
agonists/antibodies)

AM-251
AM-281
AM-630
AM-1387
AM-4113
AM-6527
AM-6545
BML-190
Brizantin (Бризантин)
CAY-10508
CB-25
CB-52
CB-86
Dietressa (Диетресса)
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LH-21
LY-320,135
MDA-77
MJ-15
MK-9470
NESS-0327
NIDA-41020
O-606
O-1184
O-1248
O-1918
O-2050
O-2654
Otenabant (CP-945,598)
PF-514273
PipISB
PSB-SB-487
Rimonabant (SR141716)
Rosonabant (E-6776)
SR-144,528
Surinabant (SR147778)
Taranabant (MK-0364)
TM-38837
VCHSR

See also: Cannabinoidergics (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics

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FUBIMINA

See also

References