2C-B-FLY is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also referred to as classic halluci ...

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. ...

of the

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 ami ...

, 2C, and FLY families. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse. This molecule was researched by

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

, and it was

Ann Shulgin Laura Ann Shulgin ( Gotlieb; March 22, 1931 – July 9, 2022) was an American author and the wife of chemist Alexander Shulgin, with whom she wrote ''PiHKAL'' and '' TiHKAL''. Life and career Laura Ann Gotlieb Detailed biography of Ann Shulgin ...

's favorite

research chemical Research chemicals are chemical substances which scientists use for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human ...

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 of little formal study, but its appearance as a

has led the

DEA The Drug Enforcement Administration (DEA) is a United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit drug trafficking and distribution within the U.S. It is the lead agency for domes ...

to release analytical results for 2C-B-FLY and several related compounds.

Analogs and derivatives

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 2C-I, also known as 2,5-dimethoxy-4-iodophenethylamine, is a phenethylamine of the 2C family with psychedelic effects. It was first synthesized by Alexander Shulgin, and is described in Shulgin's book ''PiHKAL'' (1991). The substance is con ...

, and the 8-methyl equivalent, "2C-D-FLY," would be the dihydro-difuran analogue of

2C-D 2C-D, also known as 2C-M or as 2,5-dimethoxy-4-methylphenethylamine, 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, a ...

. 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 DOB or Dob often refers to date of birth. DOB or Dob may also refer to: Biochemistry * 2,5-dimethoxy-4-bromoamphetamine, Bromo-DMA, a psychedelic drug ** Meta-DOB, related substance ** Methyl-DOB, related substance * HLA-DOB, human gene Organiz ...

, 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-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 Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

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 Latin ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usuall ...

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 betwee ...

, 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. Bfly structures for wiki2

Dosage

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

Interactions

Toxicity

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

Denmark Denmark is a Nordic countries, Nordic country in Northern Europe. It is the metropole and most populous constituent of the Kingdom of Denmark,, . also known as the Danish Realm, a constitutionally unitary state that includes the Autonomous a ...

and the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

, 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 is a potent

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

of the

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT₂ receptors, including the

5-HT_2A,

5-HT_2B, and

5-HT_2C receptors. Unusually among 2C drugs, 2C-B-FLY also shows high

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Pa ...

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".finlex.fi
/ref>

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 ...

if it is intended for human consumption given its similarity to 2C-B.

References

External links

2C-B-FLY - Isomer Design

2C-B-FLY - PsychonautWiki

2C-B-FLY - Erowid

2C-B-FLY - PiHKAL - Erowid

2C-B-FLY - PiHKAL - Isomer Design

2C-B-FLY: Is It The Best Psychedelic For Arousal & Sexual Intimacy? - Tripsitter
{{DEFAULTSORT:2c-B-Fly 2C (psychedelics) 5-HT2A agonists 5-HT2B agonists 5-HT2C agonists Alexander Shulgin Bromobenzene derivatives Designer drugs Dihydrofurans Entactogens FLY (psychedelics) Psychedelic phenethylamines Serotonin receptor agonists Substances discovered in the 1990s TAAR1 agonists