2C-B-FLY is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

and

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. D ...

of the

2C family 2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the ...

. It was first synthesized in 1996 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 ,3-f enzofuran-4-yl)ethanamine. It has been subject to little formal study, but its appearance as a

has led the DEA to release analytical results for 2C-B-FLY and several related compounds.

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 2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book '' PiHKAL'', the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is so ...

, the 8-iodo equivalent 2C-I-FLY would be the dihydrodifuran analogue of

2C-I 2C-I is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and described in his 1991 book '' PiHKAL'' (''Phenethylamines I Have Known and Loved''). The drug has been used recreationally as psychedelic and ...

, and the 8-methyl equivalent 2C-D-FLY would be the dihydrodifuran analogue of

2C-D 2C-D (2,5-dimethoxy-4-methylphenethylamine or 2C-M) is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity wa ...

. Other related compounds can also be produced, where the alpha carbon of the ethylamine chain is methylated, the amphetamine derivative

DOB-FLY DOB-FLY is a recreational designer drug with psychedelic effects. It can be regarded as the alpha-methyl derivative of 2C-B-FLY or the partially saturated counterpart of bromo-dragonfly. Unlike bromo-dragonfly, DOB-FLY is only slightly more pote ...

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 TFMFly is a compound related to psychedelic phenethylamines such as 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols. It acts as a potent agonist at the 5HT2A serotonin receptor subtype, ...

. 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 Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological ...

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 In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mo ...

at 5-HT_2A, but the saturated benzodifuran derivatives have higher

efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as ''effectiveness'', and it has often been used synonymously, although in pharmacology a distinction is now often made between ...

, 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 Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymetha ...

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

Toxicity

The toxicity of 2C-B-FLY in humans is unknown. Two deaths occurred in October 2009, in

Denmark ) , song = ( en, "King Christian stood by the lofty mast") , song_type = National and royal anthem , image_map = EU-Denmark.svg , map_caption = , subdivision_type = Sovereign state , subdivision_name = Kingdom of Denmark , establish ...

and the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...

, 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.

History

In 2019, it became part of a group of molecules studied by the french laboratory Caulredaitens.

Legality

Canada

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

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 The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed in ...

if it is intended for human consumption given its similarity to

Pharmacology

The hallucinogenic effect of 2C-B-FLY is mediated by its partial

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ag ...

ic activity at the 5-HT_2A

serotonin receptor 5-HT receptors, 5-hydroxytryptamine receptors, or serotonin receptors, are a group of G protein-coupled receptor and ligand-gated ion channels found in the central and peripheral nervous systems. They mediate both excitatory and inhibitory ne ...

, but also has a high binding affinity for the 5-HT_1D, 5-HT_1E, 5-HT_1A, 5-HT_2B and 5-HT_2C receptors. Researchers suspect that 2C-B-FLY may have a MAOI action, making it dangerous to mix it with drugs like

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desire ...

Tramadol Tramadol, sold under the brand name Ultram among others, is an opioid pain medication used to treat moderate to moderately severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an ...

References

External links

2C-B-FLY Entry at Erowid

2C-B-FLY Entry at Isomerdesign
{{DEFAULTSORT:2c-B-Fly 2C (psychedelics) Bromoarenes Designer drugs Entactogens and empathogens Phenethylamines Psychedelic phenethylamines Serotonin receptor agonists Substances discovered in the 1990s