:2C-B-FLY
{{Short description|Psychedelic designer drug}}
{{Drugbox
| IUPAC_name = 2-(4-Bromo-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl)ethanamine
| image = 2C-B-FLY structure.svg
| width =
| image2 = 2C-B-FLY 3D BS.png
| width2 =
| routes_of_administration = Oral
| class = Serotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
| legal_DE = NpSG
| legal_UK = PSA
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 733720-95-1
| PubChem = 10265873
| ChemSpiderID = 8441352
| ChEMBL = 101189
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z1T18Z40OT
| C = 12 | H = 14 | Br = 1 | N = 1 | O = 2
| SMILES = NCCc1c2CCOc2c(Br)c3CCOc13
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H14BrNO2/c13-10-9-3-6-15-11(9)7(1-4-14)8-2-5-16-12(8)10/h1-6,14H2
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YZDFADGMVOSVIX-UHFFFAOYSA-N
| melting_point = 310
}}
2C-B-FLY is a psychedelic and designer drug of the phenethylamine, 2C, and FLY families. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.{{cite web | title=Profile for Aaron Monte | website=UW-La Crosse | date=2013-04-10 | url=https://www.uwlax.edu/profile/amonte/}}{{Cite web |title=Erowid 2C-B-Fly Vaults : 2C-B-FLY |url=https://erowid.org/chemicals/2cb_fly/2cb_fly_info1.shtml |access-date=2022-11-24 |website=erowid.org}}
This molecule was researched by Alexander Shulgin, and it was Ann Shulgin's favorite research chemical.{{cite web | last=Kent | first=James | title=Remembering Psychedelic Chemist Alexander Shulgin | website=Psychedelic Spotlight | date=17 June 2022 | url=https://psychedelicspotlight.com/remembering-psychedelic-chemist-alexander-shulgin/ | access-date=26 March 2025 | quote=Ann and Sasha often experimented with psychedelics together, and shared their findings with their confidential research group. “Different people have different body types, so Sasha thought it was important to see how a drug reacts in all kinds of people.” When I ask Ann what Sasha’s favorite of his own chemicals is she knows immediately. “It would have to be 2C-B. He was always very proud of that one. He called it the Great Teacher. Although I preferred 2C-B-Fly a bit more.” But there are so many to choose from. DiPT, 5-MeO-AMT, 5-MeO-DALT, Methylone, 2C-T-7, and this list goes on. Ann can’t say for sure how many trips they shared together, she just smiles and says, “We stopped counting at around two-thousand.” This is a mind-boggling number considering the total may actually be closer to four-thousand.}}{{cite web | last=Cooke | first=Justin | title=2C-B-FLY: Is It The Best Psychedelic For Arousal & Sexual Intimacy? | website=Tripsitter | date=1 July 2021 | url=https://tripsitter.com/2cb-fly/ | access-date=26 March 2025 | quote=The overall sentiment for [2C-B-FLY] is that it’s one of the most enjoyable of the research psychedelics. Ann Shulgin — wife of Alexander Shulgin and co-author of the books TiHKAL and PiHKAL — once stated that 2C-B-FLY was one of her favorite psychedelics.}}
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=
{{2C-B analogues 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, 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 DOB-FLY, with this compound being the dihydro-difuran analogue of DOB, 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.{{clarification needed|date=December 2024}} 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.{{cite journal |author =Monte AP |title=Dihydrobenzofuran analogues of hallucinogens. 4. Mescaline derivatives |journal=Journal of Medicinal Chemistry |volume=40 |issue=19 |pages=2997–3008 |date=September 1997 |pmid=9301661 |doi=10.1021/jm970219x |display-authors=etal|citeseerx=10.1.1.690.9370 }}{{cite journal |vauthors=Chambers JJ, Kurrasch-Orbaugh DM, Nichols DE |title=Translocation of the 5-alkoxy substituent of 2,5-dialkoxyarylalkylamines to the 6-position: effects on 5-HT(2A/2C) receptor affinity |journal=Bioorganic & Medicinal Chemistry Letters |volume=12 |issue=15 |pages=1997–9 |date=August 2002 |pmid=12113827 |doi= 10.1016/S0960-894X(02)00306-2 |citeseerx=10.1.1.688.9483 }} 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.{{cite journal |author =Nichols DE |title=2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines |journal=Journal of Medicinal Chemistry |volume=34 |issue=1 |pages=276–81 |date=January 1991 |pmid=1992127 |doi= 10.1021/jm00105a043|display-authors=etal}}{{cite journal |author =Monte AP |title=Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups |journal=Journal of Medicinal Chemistry |volume=39 |issue=15 |pages=2953–61 |date=July 1996 |pmid=8709129 |doi=10.1021/jm960199j |display-authors=etal}}{{Cite thesis |type=PhD. Thesis |title=Studies of perceptiotropic phenethylamines: Determinants of affinity for the 5-HT2A receptor |url=http://bitnest.ca/external.php?id=%251C%2B95%2522%250D%2519%2518%2505%250C%250Dtz%257D%2500%2501 |author=Parker, MA |year=1998 |publisher=Purdue University |access-date=2011-12-16 |archive-url=https://web.archive.org/web/20120425132418/http://bitnest.ca/external.php?id=%1C+95%22%0D%19%18%05%0C%0Dtz%7D%00%01 |archive-date=2012-04-25 |url-status=dead }}{{cite journal |vauthors=Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE |title=Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists |journal=Journal of Medicinal Chemistry |volume=44 |issue=6 |pages=1003–10 |date=March 2001 |pmid=11300881 |doi= 10.1021/jm000491y|citeseerx=10.1.1.691.362 }}{{cite journal |author =Whiteside MS |title=Substituted hexahydrobenzodipyrans as 5-HT2A/2C receptor probes |journal=Bioorganic & Medicinal Chemistry |volume=10 |issue=10 |pages=3301–6 |date=October 2002 |pmid=12150876 |doi= 10.1016/S0968-0896(02)00209-2|display-authors=etal|citeseerx=10.1.1.1010.6813 }}{{cite journal |author =Chambers JJ |title=Synthesis and pharmacological characterization of a series of geometrically constrained 5-HT(2A/2C) receptor ligands |journal=Journal of Medicinal Chemistry |volume=46 |issue=16 |pages=3526–35 |date=July 2003 |pmid=12877591 |doi=10.1021/jm030064v |display-authors=etal|citeseerx=10.1.1.688.3544 }}{{cite journal |author =Schultz DM |title="Hybrid" Benzofuran–Benzopyran Congeners as Rigid Analogues of Hallucinogenic Phenethylamines |journal=Bioorganic & Medicinal Chemistry |volume=16 |issue=11 |pages=6242–51 |date=June 2008 |pmid=18467103 |pmc=2601679 |doi=10.1016/j.bmc.2008.04.030 |display-authors=etal}}{{Cite thesis |type=PhD. |title=Design and Synthesis of Novel 5-HT2A/2C Receptor Agonists |url=http://murphylibrary.uwlax.edu/digital/jur/2000/evans.pdf |last=Evans |first=Paul |year=2000 |publisher=University of Wisconsin-La Cross |access-date=2010-05-27 |archive-url=https://web.archive.org/web/20110716093640/http://murphylibrary.uwlax.edu/digital/jur/2000/evans.pdf |archive-date=2011-07-16 |url-status=dead }}{{Cite thesis |type=PhD. |title=Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. |url=http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 |last=Heim |first=Ralf |year=2004 |publisher=Der Freien Universität Berlin }}{{Cite thesis |type=PhD. |title=Towards a biophysical understanding of hallucinogen action |last=Braden |first=Michael Robert |year=2007 |publisher=Purdue University |id={{ProQuest|304838368}} }}{{Cite thesis |type=PhD. |title=Theoretical study of the interaction of agonists with the 5-HT2A receptor |url=http://epub.uni-regensburg.de/12119/ |last=Silva |first=Maria |year=2009 |publisher=Universität Regensburg }}
Dosage
Alexander Shulgin lists a dosage of 2C-B-FLY from 10 to 20 mg orally.{{citation needed|date=June 2021}}
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
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.{{Cite web|url=https://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml|title=Erowid 2C-B-Fly Vault: Death Reports 2009|website=www.erowid.org|accessdate=18 December 2022}}
Pharmacology
2C-B-FLY is a potent agonist of the serotonin 5-HT2 receptors, including the serotonin 5-HT2A, serotonin 5-HT2B, and serotonin 5-HT2C receptors. Unusually among 2C drugs, 2C-B-FLY also shows high affinity for the serotonin 5-HT1D receptor. It also has relatively weak affinity for the serotonin 5-HT1A, 5-HT1B, and 5-HT1E receptors.
Legality
=Canada=
As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.[http://gazette.gc.ca/rp-pr/p2/2016/2016-05-04/html/sor-dors72-eng.php Regulations Amending the Food and Drug Regulations (Part J — 2C-phenethylamines)]
=Finland=
Scheduled in the "government decree on psychoactive substances banned from the consumer market".[https://finlex.fi/fi/lainsaadanto/2014/1130 finlex.fi]
=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 if it is intended for human consumption given its similarity to 2C-B.
References
{{Reflist|40em}}
External links
- [https://isomerdesign.com/pihkal/explore/2021 2C-B-FLY - Isomer Design]
- [https://psychonautwiki.org/wiki/2C-B-FLY 2C-B-FLY - PsychonautWiki]
- [https://www.erowid.org/chemicals/2cb_fly/2cb_fly.shtml 2C-B-FLY - Erowid]
- [https://www.erowid.org/chemicals/2cb_fly/ 2C-B-FLY - PiHKAL - Erowid]
- [https://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=2021 2C-B-FLY - PiHKAL - Isomer Design]
- [https://tripsitter.com/2cb-fly/ 2C-B-FLY: Is It The Best Psychedelic For Arousal & Sexual Intimacy? - Tripsitter]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{TAAR modulators}}
{{Phenethylamines}}
{{DEFAULTSORT:2c-B-Fly}}
Category:Bromobenzene derivatives
Category:Psychedelic phenethylamines
Category:Serotonin receptor agonists