2C-B-FLY
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Melting point | 310 °C (590 °F) |
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2C-BFLY is a
This molecule was researched by Alexander Shulgin, and it was Ann Shulgin's favorite research chemical.[3]
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-NB
- 25B-NB23DM
- 25B-NB25DM
- 25B-NB3OMe
- 25B-NB4OMe
- 25B-NBF
- 25B-NBMD
- 25B-NBOH
- 25B-NBOMe (NBOMe-2CB)
- 2C-B-FLY
- 2CBFly-NBOMe (NBOMe-2CB-Fly)
- DOB-FLY
- DOB-2-DRAGONFLY-5-BUTTERFLY
Other:
- BOB
- BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB[6][7]
- 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
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]
Dosage
Alexander Shulgin lists a dosage of 2C-B-FLY from 10 to 20 mg orally[citation needed].
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.[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
Pharmacology
The hallucinogenic effect of 2C-B-FLY is mediated by its partial agonistic activity at the 5-HT2A serotonin receptor, but also has a high binding affinity for the 5-HT1D, 5-HT1E, 5-HT1A, 5-HT2B and 5-HT2C receptors.
Researchers suspect that 2C-B-FLY may have a
References
- ^ "Profile for Aaron Monte". UW-La Crosse. 2013-04-10.
- ^ "Erowid 2C-B-Fly Vaults : 2C-B-FLY". erowid.org. Retrieved 2022-11-24.
- ^ Ali, Nuit. "2C-B-FLY, Ann Shulgin's Favourite Molecule". chemical-collective.com.
- ^ "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
- ^ "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
- PMID 15537358.
- ^ Beta-hydroxyphenylalkylamines and their use for treating glaucoma
- PMID 9301661.
- PMID 12113827.
- PMID 1992127.
- PMID 8709129.
- ^ Parker, MA (1998). Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor (PhD. Thesis). Purdue University. Archived from the original on 2012-04-25. Retrieved 2011-12-16.
- PMID 11300881.
- PMID 12150876.
- PMID 12877591.
- PMID 18467103.
- ^ Evans, Paul (2000). Design and Synthesis of Novel 5-HT2A/2C Receptor Agonists (PDF) (PhD.). University of Wisconsin-La Cross. Archived from the original (PDF) on 2011-07-16. Retrieved 2010-05-27.
- ^ Heim, Ralf (2004). Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (PhD.). Der Freien Universität Berlin.
- ProQuest 304838368.
- ^ Silva, Maria (2009). Theoretical study of the interaction of agonists with the 5-HT2A receptor (PhD.). Universität Regensburg.
- ^ "Erowid 2C-B-Fly Vault: Death Reports 2009". www.erowid.org. Retrieved 18 December 2022.
- ^ Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)
- PMID 20126400.