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IUPAC name
CAS number 178557-21-6
PubChem 10265873
ChemSpider ID 8441352
Molecular formula C12H14BrNO2
Molar mass 284.15 g/mol
Melting point

310 °C, 583 K, 590 °F

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2C-B-FLY is a psychedelic phenethylamine of the 2C family. It was first synthesized by Aaron P. Monte, and is sometimes used as an entheogen.



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 to little formal study, but its appearance as a designer drug has led the DEA to release analytical results for 2CB-FLY and several related compounds.[1]

In theory, dihydrodifuran analogues of any of the 2Cx / DOx family of drugs could be made, and would be expected to show similar activity to the parent compound. So in the same way that 2C-B-FLY is the dihydrodifuran analogue of 2C-B, the 8-iodo equivalent 2C-I-FLY would be the dihydrodifuran analogue of 2C-I, and the 8-methyl equivalent 2C-M-FLY would be the dihydrodifuran analogue of 2C-D.

Other related compounds can also be produced, where the alpha carbon of the ethylamine chain is methylated, the amphetamine derivative 3C-B-FLY would be made, this compound being the dihydrodifuran analogue of DOB, and would also be the unsaturated equivalent of Bromo-DragonFLY.

Where only one methoxy group of a 2Cx drug is cyclised into a dihydrofuran ring, the resulting compound is known as a "hemifly"and, when a saturated furan ring is used, the compound is known as a "hemi-dragonfly". A large family of compounds can thus be derived, many of which can be predicted to be active hallucinogens based on the known structure-activity relationships of these drugs, although most of these compounds have not yet been made and tested.

2C-B-FLY SAR.png


Alexander Shulgin lists a dosage of 2C-B-FLY at 10 mg orally.


2C-B-FLY produces psychedelic effects that last 6–8 hours, or up to 12 hours in larger doses.


The toxicity of 2C-B-FLY in humans is unknown, but two deaths occurred in October 2009, in Denmark and the United States, after ingestion of a substance that was sold as 2C-B-FLY from Haupt-RC, but in fact consisted of mainly bromodragonfly contaminated with unidentified impurities.[2 ]


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. Possible prosecution may also occur under the same act in USA[3].


The hallucinogenic effect of 2C-B-FLY is mediated by its partial agonistic activity at the 5-HT2A serotonin receptor, but 2C-B-FLY also has a high binding affinity for the 5-HT2B and 5-HT2C serotonin receptor.[4]

External links


  1. ^ Reed EC, Kiddon GS. The Characterization of Three FLY Compounds (2C-B-FLY, 3C-B-FLY, and Bromo-DragonFLY) DEA Microgram Journal. 2007;Volume 5, Numbers 1-4
  2. ^ "Erowid 2C-B-Fly Vault: Death Report".  
  3. ^ 2cbfly DMTTRIP.COM
  4. ^ Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE. Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups. Journal of Medicinal Chemistry. 1996 Jul 19;39(15):2953-61. PMID 8709129

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