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Description

2C-B-FLY Also known as:

  • 2-(8-Brom-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)ethanamin[German][ACD/IUPAC Name]
  • 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)ethanamine
  • 2-(8-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)ethanamine[ACD/IUPAC Name]
  • 2-(8-Bromo-2,3,6,7-tétrahydrofuro[2,3-f][1]benzofuran-4-yl)éthanamine[French][ACD/IUPAC Name]
  • 2C-B-Fly
  • 8-BROMO-2,3,6,7-TETRAHYDROBENZO(1,2-B:4,5-B')DIFURAN-4-ETHANAMINE
  • Benzo[1,2-b:4,5-b']difuran-4-ethanamine, 8-bromo-2,3,6,7-tetrahydro-[ACD/Index Name]
  • 2-(4-bromo-2,3,6,7-tetrahydrofuro[2,3-f]benzofuran-8-yl)ethanamine
  • 2-(8-Bromo-2,3,6,7-tetrahydro-benzo[1,2-b
  • 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b]difuran-4-yl)ethanamine
  • 2-(8-Bromo-2,3,6,7-tetrahydrobenzo-[1,2-b:4,5-b']difuran-4-yl)ethanamine
  • 2-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b`]difuran-4-yl)ethanamine
  • 2-(8-Bromo-2,3,6,7-tetrahydro-benzo[1,2-b;4,5-b']difuran-4-yl)-ethylamine
  • 2-(8-Bromo-2,3,6,7-tetrahydrobenzofuro[5,6-b]furan-4-yl)ethanamine hydrochloride
  • 2-(8-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofurane-4-yl)ethanamine[ACD/IUPAC Name]
  • 4,5-b']difuran-4-yl)-ethylamine
  • 8-bromo-2,3,6,7-benzo-dihydro-difurane-ethylamine[ACD/IUPAC Name]
  • MFCD22371819

Psychedelic phenethylamine that is the dihydrodifuran analog of 2C-B.

Summary

Reports have characterized its effects profile as possessing features of 2C-B, mescaline and MDA, with a duration of 6–8 hours (or up to 12 hours in larger doses). 2C-B-FLY is a derivative of the 2C-x family of psychedelic phenethylamines, specifically 2C-B, of which it significantly differs from in terms of its potency, metabolism, and potential toxicity. It was first synthesized by Aaron P.

Monte in 1996. Around 2005, 2C-B-FLY appeared and gained some popularity in the online research chemicals market before largely disappearing in October 2009, when a batch of Bromo-DragonFLY was accidentally mislabeled as 2C-B-FLY (Bromo-DragonFLY is dosed in micrograms, where 2C-B-FLY is dosed in milligrams) led to two deaths as a result of taking overdoses of Bromo-DragonFLY meant to be effective doses for 2C-B-FLY. This event led to its immediate withdrawal until around 2016, when it resurfaced on the market again.

Very little data exists about the pharmacological properties, metabolism, and toxicity of 2C-B-FLY, and it has little history of human usage. It has no documented history of being sold on the streets and is commercially distributed through online research chemical vendors. Due to its high potency and sensitive dose-response, many reports also indicate that the effects of this substance should not be seen as a simple substitute for 2C-B.

It is highly advised to approach this potent, long-lasting, and unpredictable hallucinogenic substance with the proper amount of precaution and harm reduction practices if choosing to use it.

History

In a 2007 MAPS newsletter interview, Ann Shulgin revealed that 2C-B-FLY as one of her favorite psychedelic substances while also acknowledging the high variability in responses it seemed to display.

I said often, too often, that something called 2CB Fly (sic) was absolutely great for me. To me, it’s the loveliest thing, especially for eroticism. But I found out that it’s not interesting to anybody else.

I realized that having said that, I was putting things in motion. The Internet was full of 2CB Fly (sic), and people were asking about it and I thought “uh-oh.” It turned out that it’s a disappointment to most other people.

— Ann Shulgin

Chemistry

2C-B-FLY

2C-B-FLY

2C-B-FLY features a phenyl ring bound to an amino (NH2) group through an ethyl chain and contains a bromine atom attached to carbon R4 of the phenyl ring. It is an atypical psychedelic phenethylamine which is closely analogous to 2C-B; it is the dihydrofuran analog to 2C-B, where it incorporates the methoxy groups bound to R2 and R5 of 2C-B into five-member dihydrofuran rings fused to the central benzene ring. 2C-B-FLY belongs to a group of phenethylamine derivatives referred to as the FLY compounds, named for their insect-like appearance of two “wing-like” tetrahydrofuran rings fused on the opposite sides of the central benzene ring.

The incorporation of the two methoxy groups into the 5 member rings fixes them into the optimum position for binding to the receptors they interact with resulting in an increase in potency compared to the compound’s non-rigid counterpart 2C-B.

Common Name8-BROMO-2,3,6,7-TETRAHYDROBENZO(1,2-B:4,5-B')DIFURAN-4-ETHANAMINE
Systematic name8-BROMO-2,3,6,7-TETRAHYDROBENZO(1,2-B:4,5-B')DIFURAN-4-ETHANAMINE
FormulaC_{12}H_{14}BrNO_{2}
SMILESC1COc2c1c(c3c(c2Br)CCO3)CCN
Std. InChiInChI=1S/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2
Std. InChiKeyYZDFADGMVOSVIX-UHFFFAOYSA-N
Avg. Mass284.1491 Da
Molecular Weight284.1491
Monoisotopic Mass283.020782 Da
Nominal Mass283
ChemSpider ID8441352

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Dose Chart

Oral
Light5-10mg
Common10-18mg
Strong18-25mg
Heavy25mg+

Duration Chart

2C-B-FLY Duration Data
Onset30-90 minutes
Duration6-12 hours
After-effects1-24 hours

Auditory Effects

Psychological Effects

2C-B-FLY tends to maintain a level of relatively normal and sober thought structure regardless of the subjective visual, physical and cognitive accompanying effects intensity. This leaves the user in control in a manner which would not be possible on many compounds such as 4-AcO-DMT or LSD due to their accompanying confusion and delusions.

Pharmacological Effects

Little is known about how the totality of its effects are produced, 2C-B-FLY’s psychedelic effects are believed to come from its efficacy at the 5-HT2A receptor as a partial agonist. However, the role of these interactions and how they result in the psychedelic experience remains subject to on-going scientific investigation.

Physical Effects

The physical effects of 2C-B-FLY are comparable to that of traditional phenethylamines such as 2C-E, mescaline and 2C-T-7 along with more pronounced side effects. There have been reports gastrointestinal disturbances following the use of this compound which include diarrhea, nausea, moderate to severe stomach bloating and general gassiness at moderate to heavy doses. These effects are comparable to that of 5-MeO-MiPT, 2C-T-7 and other compounds with suspected MAO-altering properties. This suggests that 2C-B-FLY may potentially have such MAO-altering properties of its own, which may make it dangerous to combine with certain substances.

Subjective Effects

In comparison to 2C-B, this compound presents a significantly more pronounced body high/load, stronger visual effects, more complex geometry and more in-depth internal hallucinations which are comparable to mescaline, 2C-E or MDA at higher doses. Lower doses, however, are associated with more entactogenic as opposed to classical psychedelic effects.

Visual Effects

Enhancements

Distortions

Geometry

The visual geometry that is present throughout this trip can be described as more similar in appearance to that of mescaline, 2C-B and 2C-D than psilocin or ayahuasca. It can be comprehensively described through its style variations as intricate in complexity, abstract in form, synthetic in style, structured in organization, brightly lit and multicoloured in scheme, glossy in shading, flat in edges, large in size, fast in speed, smooth in motion, angular in corners, non-immersive in-depth and consistent in intensity. They have a contradictory combination of a very "natural" but also "neon digital" feel to them and at higher dosages are significantly more likely to result in states of level 8B visual geometry over level 8A.

Hallucinatory states

2C-B-FLY produces a moderate range of hallucinatory states in a fashion that is comparable to mescaline or common doses of 2C-E. This is more consistent and reproducible than that of many other commonly used psychedelics such as 2C-B or LSD. It tends to occur at heavier dosages and integrates seamlessly with the accompanying geometry. These effects generally include:

Legal Status

  • Austria: 2C-B-FLY is illegal to possess, produce and sell under the NPSG. (Neue-Psychoaktive-Substanzen-Gesetz Österreich).
  • Canada: 2C-B-FLY would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.
  • Germany: 2C-B-FLY is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016. Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized.
  • United Kingdom: It is illegal to produce, supply, or import this drug under the Psychoactive Substance Act, which came into effect on May 26th, 2016.
  • United States: 2C-B-FLY is unscheduled and uncontrolled in the United States. However, it may fall under the scope of the Federal Analogue Act if it is intended for human consumption given its similarity to 2C-B.
  • Sweden: As of April 2018, 2C-B-FLY is illegal to possess, sell, buy and use under Swedish law.
  • Sources

    References

    1. https://erowid.org/chemicals/2cb_fly/2cb_fly_info1.shtml
    2. http://www.sciencedirect.com/topics/page/2C-B-FLY
    3. Information on Reported Deaths Related to 2C-B-FLY | https://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml
    4. http://www.maps.org/news-letters/v17n2/v17n2_annshulgin-23.pdf
    5. http://heffter.org/docs/hrireview/01/chapter5.pdf
    6. Talaie, H.; Panahandeh, R.; Fayaznouri, M. R.; Asadi, Z.; Abdollahi, M. (2009). "Dose-independent occurrence of seizure with tramadol". Journal of Medical Toxicology. 5 (2): 63–67. :10.1007/BF03161089.  1556-9039.
    7. Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling | http://pubs.acs.org/doi/abs/10.1021/jm0493109
    8. Controlled Drugs and Substances Act (S.C. 1996, c. 19) |http://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-12.html#h-28
    9. "Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe" (PDF) (in German). Bundesanzeiger Verlag. Retrieved December 11, 2019.
    10. "Anlage NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    11. "§ 4 NpSG" (in German). Bundesministerium der Justiz und für Verbraucherschutz. Retrieved December 11, 2019.
    12. Psychoactive Substances Act 2016 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted
    13. https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2018/februari/tio-nya-amnen-kan-klassas-som-narkotika-eller-halsofarlig-vara/

    Information made possible with:

    1. PsychonautWiki is a community-driven online encyclopedia that aims to document the field of psychonautics in a comprehensive, scientifically-grounded manner.
    2. Erowid is a non-profit educational & harm-reduction resource with 60 thousand pages of online information about psychoactive drugs
    3. PubChem National Center for Bio Informatics
    4. Chemspider is a free chemical structure database providing fast access to over 34 million structures, properties and associated information.
    5. Wikipedia

    Additional APIs were used to construct this information. Thanks to ChemSpider, NCBI, PubChem etc.

    Data is constantly updated so please check back later to see if there is any more available information on this substance.