Definition and meaning of 2C-B-FLY

2C-B-FLY
IUPAC name 2-(8-bromo-2,3,6,7-tetrahydrofuro [2,3-f][1]benzofuran-4-yl)ethanamine
Identifiers
CAS number	178557-21-6 Y
PubChem	10265873
ChemSpider	8441352 Y
ChEMBL	CHEMBL101189 Y
Jmol-3D images	Image 1
SMILES Brc3c1c(OCC1)c(c2c3OCC2)CCN
InChI InChI=1S/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2 Y Key: YZDFADGMVOSVIX-UHFFFAOYSA-N Y InChI=1/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2 Key: YZDFADGMVOSVIX-UHFFFAOYAQ
Properties
Molecular formula	C12H14BrNO2
Molar mass	284.15 g/mol
Melting point	310 °C, 583 K, 590 °F
Y (verify) (what is: Y/N?) 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.

  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 to 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.^[1]

  Analogues and derivatives

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-D-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 DOB-FLY can be made, this compound being the dihydrodifuran analogue of DOB, or conversely can be viewed as the saturated derivative 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 an unsaturated furan ring is used, the compound is known as a "hemi-dragonfly". The larger saturated hexahydrobenzodipyran ring derivatives have been referred to as "butterfly" compounds. The 8-bromo group can also be replaced by other groups to give compounds such as TFMFly.

A large number of symmetrical and unsymmetrical derivatives can be produced by using different combinations of ring systems. Because the 2- and 5- positions (using phenethylamine numbering scheme, 1,5-positions if numbered as benzodifuran) are not equivalent, all unsymmetrical combinations also have two possible positional isomers, with different potencies at the various 5-HT₂ subtypes. 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.^[2][3] 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.^{[4][5][6][7][8][9][10][11][12][13][14]}

  Dosage

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

  Effects

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

  Toxicity

The toxicity of 2C-B-FLY in humans is unknown. Worldwide, there are no known deaths. 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 Bromo-DragonFLY contaminated with a small amount of unidentified impurities.^[15]

  Legality

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.^[16]

  Pharmacology

The hallucinogenic effect of 2C-B-FLY is mediated by its partial agonistic activity at the 5-HT_2A serotonin receptor, but 2C-B-FLY also has a high binding affinity for the 5-HT_2B and 5-HT_2C serotonin receptor.

  External links

• 2C-B-FLY Entry at Erowid

  References

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. ^ Monte AP, Waldman SR, Marona-Lewicka D, Wainscott DB, Nelson DL, Sanders-Bush E, Nichols DE (September 1997). "Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives". Journal of Medicinal Chemistry 40 (19): 2997–3008. doi:10.1021/jm970219x. PMID 9301661. 
3. ^ 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. doi:10.1016/S0960-894X(02)00306-2. PMID 12113827. 
4. ^ Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". Journal of Medicinal Chemistry 34 (1): 276–81. doi:10.1021/jm00105a043. PMID 1992127. 
5. ^ Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE (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. PMID 8709129. 
6. ^ Parker, MA. Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor. PhD. Thesis, Purdue University, 1998.
7. ^ Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE (March 2001). "Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists". Journal of Medicinal Chemistry 44 (6): 1003–10. doi:10.1021/jm000491y. PMID 11300881. 
8. ^ Whiteside MS, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE, Monte A (October 2002). "Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes". Bioorganic & Medicinal Chemistry 10 (10): 3301–6. doi:10.1016/S0968-0896(02)00209-2. PMID 12150876. 
9. ^ Chambers JJ, Parrish JC, Jensen NH, Kurrasch-Orbaugh DM, Marona-Lewicka D, Nichols DE (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. doi:10.1021/jm030064v. PMID 12877591. 
10. ^ Schultz DM, Prescher JA, Kidd S, Marona-Lewicka D, Nichols DE, Monte A (June 2008). ""Hybrid" Benzofuran–Benzopyran Congeners as Rigid Analogues of Hallucinogenic Phenethylamines". Bioorganic & Medicinal Chemistry 16 (11): 6242–51. doi:10.1016/j.bmc.2008.04.030. PMC 2601679. PMID 18467103. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2601679. 
11. ^ Paul Evans PhD. Design and Synthesis of Novel 5-HT2A/2C Receptor Agonists. University of Wisconsin-La Cross, 2000
12. ^ Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German). Der Freien Universität Berlin, 2004.
13. ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
14. ^ Maria Silva PhD. Theoretical study of the interaction of agonists with the 5-HT2A receptor. Universität Regensburg, 2009.
15. ^ "Erowid 2C-B-Fly Vault: Death Report". http://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml. 
16. ^ 2cbfly DMTTRIP.COM