FUBIMINA

Last updated
FUBIMINA
FUBIMINA structure.png
Legal status
Legal status
Identifiers
  • (1-(5-fluoropentyl)-1H-benzo[d]imidazol-2-yl)(naphthalen-1-yl)methanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C23H21FN2O
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 (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

Related Research Articles

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<span class="mw-page-title-main">AM-2201</span> Chemical compound

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<span class="mw-page-title-main">UR-144</span> Chemical compound

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<span class="mw-page-title-main">EAM-2201</span> Chemical compound

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<span class="mw-page-title-main">APICA (synthetic cannabinoid drug)</span> Chemical compound

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<span class="mw-page-title-main">PB-22</span> Chemical compound

PB-22 is a designer drug offered by online vendors as a cannabimimetic agent, and detected being sold in synthetic cannabis products in Japan in 2013. PB-22 represents a structurally unique synthetic cannabinoid chemotype, since it contains an ester linker at the indole 3-position, rather than the precedented ketone of JWH-018 and its analogs, or the amide of APICA and its analogs.

<span class="mw-page-title-main">5F-PB-22</span> Chemical compound

5F-PB-22 is a designer drug which acts as a cannabinoid agonist. The structure of 5F-PB-22 appears to have been designed with an understanding of structure–activity relationships within the indole class of cannabinoids.

<span class="mw-page-title-main">SDB-006</span> Chemical compound

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<span class="mw-page-title-main">25N-NBOMe</span> Chemical compound

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<span class="mw-page-title-main">THJ-2201</span> Synthetic cannabinoid

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<span class="mw-page-title-main">5F-AMB</span> Chemical compound

5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in early 2014. Although only very little pharmacological information about 5F-AMB itself exists, its 4-cyanobutyl analogue (instead of 5-fluoropentyl) has been reported to be a potent agonist for the CB1 receptor (KI = 0.7 nM).

<span class="mw-page-title-main">Mepirapim</span> Chemical compound

MEPIRAPIM is an indole-based cannabinoid which differs from JWH-018 by having a 4-methylpiperazine group in place of the naphthyl group and has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in 2013, alongside FUBIMINA. MEPIRAPIM acts as a T-type calcium channel inhibitor and is only minimally active at the central CB1 receptor.

<span class="mw-page-title-main">NNE1</span>

NNE1 (also known as NNEI, MN-24 and AM-6527) is an indole-based synthetic cannabinoid, representing a molecular hybrid of APICA and JWH-018 that is an agonist for the cannabinoid receptors, with Ki values of 60.09 nM at CB1 and 45.298 nM at CB2 and EC50 values of 9.481 nM at CB1 and 1.008 nM at CB2. It was invented by Abbott and has a CB1 receptor pEC50 of 8.9 with around 80x selectivity over the related CB2 receptor. It is suspected that metabolic hydrolysis of the amide group of NNE1 may release 1-naphthylamine, a known carcinogen, given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, and NNE1 was banned in New Zealand in 2012 as a temporary class drug to stop it being used as an ingredient in then-legal synthetic cannabis products. NNE1 was subsequently found to be responsible for the death of a man in Japan in 2014.

<span class="mw-page-title-main">THJ-018</span> Chemical compound

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<span class="mw-page-title-main">NM-2201</span> Chemical compound

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<span class="mw-page-title-main">FDU-PB-22</span> Chemical compound

FDU-PB-22 is a derivative of JWH-018 that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug.

<span class="mw-page-title-main">BIM-018</span> Chemical compound

BIM-018 is a synthetic cannabinoid that is the benzimidazole analog of JWH-018. It is presumed to be a potent agonist of the CB2 receptor and has been sold online as a designer drug.

<span class="mw-page-title-main">EG-018</span>

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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. 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. 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 (3): 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.