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

<span class="mw-page-title-main">MN-18</span> Chemical compound

MN 18 is an indazole-based synthetic cannabinoid that is an agonist for the cannabinoid receptors, with Ki values of 45.72 nM at CB1 and 11.098 nM at CB2 and EC50 values of 2.028 nM at CB1 and 1.233 nM at CB2, and has been sold online as a designer drug. It is the indazole core analogue of NNE1. Given the known metabolic liberation (and presence as an impurity) of amantadine in the related compound APINACA, it is suspected that metabolic hydrolysis of the amide group of MN-18 may release 1-naphthylamine, a known carcinogen. MN-18 metabolism has been described in literature.

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

JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in animals similar to those of tetrahydrocannabinol (THC), a cannabinoid naturally present in cannabis, leading to its use as synthetic cannabinoid products that, in some countries, are sold legally as "incense blends".

<span class="mw-page-title-main">AM-694</span> Chemical compound

AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer drug that acts as a potent and selective agonist for the cannabinoid receptor CB1. It is used in scientific research for mapping the distribution of CB1 receptors.

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

AM-2201 is a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor. It is part of the AM series of cannabinoids discovered by Alexandros Makriyannis at Northeastern University.

<span class="mw-page-title-main">AM-2232</span> Cannabinoid receptor agonist

AM-2232 (1-(4-cyanobutyl)-3-(naphthalen-1-oyl)indole) is a drug that acts as a potent but unselective agonist for the cannabinoid receptors, with a Ki of 0.28 nM at CB1 and 1.48 nM at CB2.

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

UR-144 (TMCP-018, KM-X1, MN-001, YX-17) is a drug invented by Abbott Laboratories, that acts as a selective full agonist of the peripheral cannabinoid receptor CB2, but with much lower affinity for the psychoactive CB1 receptor.

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

EAM-2201 is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laboratories in Japan in July 2012 as an ingredient in synthetic cannabis smoking blends Like the closely related MAM-2201 which had been first reported around a year earlier, EAM-2201 thus appears to be another novel compound invented by designer drug suppliers specifically for recreational use. Structurally, EAM-2201 is a hybrid of two known cannabinoid compounds JWH-210 and AM-2201, both of which had previously been used as active ingredients in synthetic cannabis blends before being banned in many countries.

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

APICA is an indole based drug that acts as a potent agonist for the cannabinoid receptors.

<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

SDB-006 is a drug that acts as a potent agonist for the cannabinoid receptors, with an EC50 of 19 nM for human CB2 receptors, and 134 nM for human CB1 receptors. It was discovered during research into the related compound SDB-001 which had been sold illicitly as "2NE1". SDB-006 metabolism has been described in literature.

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

THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor and has been sold online as a designer drug.

<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> Chemical compound

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

THJ-018 (SGT-17) is a synthetic cannabinoid that is the indazole analogue of JWH-018 and has been sold online as a designer drug.

<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">FUB-PB-22</span> Chemical compound

FUB-PB-22 (QUFUBIC) is an indole-based synthetic cannabinoid that is 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> Chemical compound

EG-018 is a carbazole-based synthetic cannabinoid that has been sold online as a designer drug. It acts as a partial agonist of the CB1 and CB2 receptor, with reasonably high binding affinity, but low efficacy in terms of inducing a signaling response.

References

  1. "FUBIMINA". Cayman Chemical. Retrieved 22 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.