# 2C-B-FLY

2C-B-FLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.
This molecule was researched by Alexander Shulgin, and it was Ann Shulgin's favorite research chemical.

## Chemistry

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.

### Analogs and derivatives

Analogues and derivatives of 2C-B:
25-N:
* 25B-N1POMe
* 25B-NAcPip
25-NB:
* 25B-NB
* 25B-NB23DM
* 25B-NB25DM
* 25B-NB3OMe
* 25B-NB4OMe
* 25B-NBF
* 25B-NBMD
* 25B-NBOH
* 25B-NBOMe (NBOMe-2CB)
** DMBMPP
25-NM:
* 25B-NMe7BF
* 25B-NMe7BT
* 25B-NMe7Bim
* 25B-NMe7Box
* 25B-NMe7DHBF
* 25B-NMe7Ind
* 25B-NMe7Indz
* 25B-NMePyr
Substituted benzofurans:
* 2C-B-FLY
** 2C-B-BUTTERFLY
** 2C-B-DRAGONFLY
* 2CBFly-NBOMe (NBOMe-2CB-Fly)
* DOB-FLY
* DOB-2-DRAGONFLY-5-BUTTERFLY
N-(2C)-fentanyl:
* N-(2C-B) fentanyl
** N-(2C-B-FLY) fentanyl
Other:
* BOB
* BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB
* BMB
* 2C-B-5-hemifly
* 2C-B-aminorex (2C-B-AR)
* 2C-B-AN
* 2C-B-BZP
* 2C-B-FLY-NB2EtO5Cl
* 2C-B-PP
* 2CB-Ind
* βk-2C-B (beta-keto 2C-B)
* N-Ethyl-2C-B
* TCB-2 (2C-BCB)
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-HT$_2$ 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-HT$_{2A}$, but the saturated benzodifuran derivatives have higher efficacy, while the saturated benzodipyran derivatives are more selective for 5-HT$_{2C}$. 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.

## Dosage

Alexander Shulgin lists a dosage of 2C-B-FLY from 10 to 20 mg orally.

## 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.

## Pharmacology

2C-B-FLY activities :
| Target | Affinity (K$_i$, nM) |
| 5-HT$_{1A}$ | 147–350 |
| 5-HT$_{1B}$ | 185 |
| 5-HT$_{1D}$ | 1.4 |
| 5-HT$_{1E}$ | 110 |
| 5-HT$_{1F}$ | ND |
| 5-HT$_{2A}$ | 11–11.6 (K$_i$) 0.029–53.7 (EC$_{50}$Tooltip half-maximal effective concentration) 80–104% (E$_{max}$Tooltip maximal efficacy) |
| 5-HT$_{2B}$ | 0.9 (K$_i$) 0.123–40 (EC$_{50}$) 56–108% (E$_{max}$) |
| 5-HT$_{2C}$ | 10.6–12 (K$_i$) 0.0615–0.149 (EC$_{50}$) 100–108% (E$_{max}$) |
| 5-HT$_3$ | >10,000 |
| 5-HT$_4$ | ND |
| 5-HT$_{5A}$ | >10,000 |
| 5-HT$_6$ | 150 |
| 5-HT$_7$ | 606 |
| α$_{1A}$ | 11,000 |
| α$_{1B}$ | >10,000 |
| α$_{1D}$ | ND |
| α$_{2A}$ | 145–780 |
| α$_{2B}$ | 624 |
| α$_{2C}$ | 233 |
| β$_1$ | >10,000 |
| β$_2$ | >10,000 |
| β$_3$ | ND |
| D$_1$ | 1,400–4,963 |
| D$_2$ | 1,900–6,835 |
| D$_3$ | 6,800 |
| D$_4$ | >10,000 |
| D$_5$ | >10,000 |
| H$_1$ | 3,400–5,753 |
| H$_2$–H$_4$ | >10,000 |
| M$_1$ | 643 |
| M$_2$ | 2,029 |
| M$_3$ | 339 |
| M$_4$ | 520 |
| M$_5$ | 873 |
| I$_1$ | >10,000 |
| σ$_1$ | >10,000 |
| σ$_2$ | >10,000 |
| TAAR1Tooltip Trace amine-associated receptor 1 | 710 (K$_i$) (mouse) 30 (K$_i$) (rat) 1,800 (EC$_{50}$) (mouse) 270 (EC$_{50}$) (rat) >30,000 (EC$_{50}$) (human) 49% (E$_{max}$) (mouse) 48% (E$_{max}$) (rat) |
| SERTTooltip Serotonin transporter | 10,000 (K$_i$) 73,000 (IC$_{50}$Tooltip half-maximal inhibitory concentration) (EC$_{50}$) |
| NETTooltip Norepinephrine transporter | 17,000 (K$_i$) 97,000 (IC$_{50}$) (EC$_{50}$) |
| DATTooltip Dopamine transporter | >26,000 (K$_i$) 187,000 (IC$_{50}$) (EC$_{50}$) |
| MAO-ATooltip Monoamine oxidase A | 19,000 (IC$_{50}$) |
| MAO-BTooltip Monoamine oxidase B | ND (IC$_{50}$) |
| Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: ||
2C-B-FLY is a potent agonist of the serotonin 5-HT$_2$ receptors, including the serotonin 5-HT$_{2A}$, serotonin 5-HT$_{2B}$, and serotonin 5-HT$_{2C}$ receptors. Unusually among 2C drugs, 2C-B-FLY also shows high affinity for the serotonin 5-HT$_{1D}$ receptor. It also has relatively weak affinity for the serotonin 5-HT$_{1A}$, 5-HT$_{1B}$, and 5-HT$_{1E}$ receptors.

## Legality
### Canada

As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.

### Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market".

### 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.