2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-(8-bromo-2,3,6,7-tetrahydrofuro[2,3-f] [1]benzofuran-4-yl)ethanamine. It has been subject of little formal study, but its appearance as a designer drug has led the DEA to release analytical results for 2C-B-FLY and several related compounds.
In theory, dihydro-difuran analogs of any of the 2Cx / DOx family of drugs could be made, and would be expected to show similar activity to the parent compounds, 2-CB, DOB, DOM, etc. In the same way that 2C-B-FLY is the dihydro-difuran analog of 2C-B, the 8-iodo equivalent, "2C-I-FLY," would be the dihydro-difuran analogue of 2C-I, and the 8-methyl equivalent, "2C-D-FLY," would be the dihydro-difuran analogue of 2C-D.
Other related compounds can also be imagined and produced in which the alpha carbon of the ethylamine sidechain is methylated, giving the amphetamine derivative DOB-FLY, with this compound being the dihydro-difuran analogue of DOB, which can be viewed as the fully unsaturated derivative of Bromo-DragonFLY.
When only one methoxy group of a 2Cx drug is cyclized into a dihydro-furan ring, the resulting compound is known as a "hemifly", (and these could be termed 2- or 5- "hemis," depending on where the single dihydro-furan ring is placed). And when an unsaturated furan ring is inserted, the compound is known as a "hemi-dragonfly". The larger, fully saturated, hexahydro-benzo-dipyran ring derivative has been referred to as "2C-B-MOTH." The 8-bromo group can also be replaced by other groups to produce compounds such as TFMFly.
A large number of symmetrical and asymmetrical derivatives can be produced by using different combinations of ring systems. Because the 2- and 5- positions (using the common phenylethylamine numbering scheme), the 2- and 5-positions of the benzene ring, if named as benzo-difurans are not equivalent.[clarification needed] Asymmetrical combinations have two possible positional isomers, with different pharmacological activities, at the various 5-HT2 subtypes. These compounds were casually referred to as the "2C-B-GNAT," and "2C-B-FLEA" compounds, which contain 5 or 6 membered rings at the 2- vs. 5-positions, respectively. Isomeric "Ψ"-derivatives with the oxygens positioned at the 2,6- positions, and mescaline analogues with the oxygens at 3,5- have also been made, but both are less potent than the corresponding 2,5- isomers.[8][9] The symmetrical aromatic benzodifuran derivatives tend to have the highest binding affinity at 5-HT2A, but the saturated benzodifuran derivatives have higher efficacy, while the saturated benzodipyran derivatives are more selective for 5-HT2C. A large number of possible combinations have been synthesised and tested for activity, but these represent only a fraction of the many variations that could be produced.[10][11][12][13][14][15][16][17][18][19][20]
The toxicity of 2C-B-FLY in humans is unknown. Two deaths occurred in October 2009, in Denmark and the United States, after ingestion of a substance that was sold as 2C-B-FLY in a small-time RC shop, but in fact consisted of Bromo-DragonFLY contaminated with a small amount of unidentified impurities.[21]
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:[22][23][24][25][26][27][28][29]
As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.[30]
Finland
Scheduled in the "government decree on psychoactive substances banned from the consumer market".[31]
United States
2C-B-FLY is unscheduled and uncontrolled in the United States. However, it may fall under the scope of the Federal Analog Act if it is intended for human consumption given its similarity to 2C-B.
↑ Chambers JJ, Kurrasch-Orbaugh DM, Nichols DE (August 2002). "Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity". Bioorganic & Medicinal Chemistry Letters. 12 (15): 1997–9. CiteSeerX10.1.1.688.9483. doi:10.1016/S0960-894X(02)00306-2. PMID12113827.
↑ Nichols DE; etal. (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–81. doi:10.1021/jm00105a043. PMID1992127.
↑ Monte AP; etal. (July 1996). "Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups". Journal of Medicinal Chemistry. 39 (15): 2953–61. doi:10.1021/jm960199j. PMID8709129.
↑ Chambers JJ; etal. (July 2003). "Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands". Journal of Medicinal Chemistry. 46 (16): 3526–35. CiteSeerX10.1.1.688.3544. doi:10.1021/jm030064v. PMID12877591.
↑ Pottie E, Cannaert A, Stove CP (October 2020). "In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor". Arch Toxicol. 94 (10): 3449–3460. Bibcode:2020ArTox..94.3449P. doi:10.1007/s00204-020-02836-w. hdl:1854/LU-8687071. PMID32627074.
↑ Wagmann L, Brandt SD, Stratford A, Maurer HH, Meyer MR (February 2019). "Interactions of phenethylamine-derived psychoactive substances of the 2C-series with human monoamine oxidases". Drug Test Anal. 11 (2): 318–324. doi:10.1002/dta.2494. PMID30188017.
↑ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID26791601.
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the List of trace amines, TAAR, and TAAR1 pages. See also:Receptor/signaling modulators
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