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. 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]
Legality
Canada
As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.[22]
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.
Pharmacology
The hallucinogenic effect of 2C-B-FLY is mediated by its partial
agonistic activity at the 5-HT2Aserotonin receptor, but also has a high
bindingaffinity for the 5-HT1D, 5-HT1E, 5-HT1A, 5-HT2B and 5-HT2C receptors.
Researchers suspect that 2C-B-FLY may have a
MAOI action, making it dangerous to mix it with drugs like
MDMA or
Tramadol.[23]
^Monte AP; et al. (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". Journal of Medicinal Chemistry. 40 (19): 2997–3008.
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^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.
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^Nichols DE; et al. (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry. 34 (1): 276–81.
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PMID1992127.
^Monte AP; et al. (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.
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^Chambers JJ; et al. (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.
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