2C-B-FLY
2C-B-FLY is a psychedelic and designer drug of the phenethylamine, 2C, and FLY families. It was first described in 1995 by Aaron Monte, Professor of Chemistry at UW-La Crosse.
Use and effects
2C-B-FLY was not included nor mentioned in Alexander Shulgin's 1991 book PiHKAL. In his subsequent 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds however, he listed 2C-B-FLY's dose as 2.5 to 10mg orally. On the other hand, other sources give 2C-B-FLY's typical dose range as 10 to 20mg orally. The duration of 2C-B-FLY is said to be 6 to 10hours but up to 20hours. The effects of 2C-B-FLY have been reported to include euphoria, enhanced interpersonal communication, improved mood, closed- and open-eye visuals such as brightening of colors and visual hallucinations, feelings of insight, stimulation, tactile enhancement, sexual enhancement, and altered time perception. Other reported effects include pupil dilation, muscle twitching, restlessness, tachycardia, and body temperature changes.Toxicity
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.Interactions
Pharmacology
Pharmacodynamics
2C-B-FLY is a potent agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, serotonin 5-HT2B, and serotonin 5-HT2C receptors. Unusually among 2C drugs, 2C-B-FLY also shows high affinity for the serotonin 5-HT1D receptor. It also has relatively weak affinity for the serotonin 5-HT1A, 5-HT1B, and 5-HT1E receptors. The drug shows biased agonism at the serotonin 5-HT2C receptor.Chemistry
2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-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.Analogues and derivatives
s of 2C-B-FLY include 2C-B, DOB-FLY, and Bromo-DragonFLY, among others.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 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, 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. 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.