View source for 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 administration|Oral]]
| class = [[Serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> 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

<!--Chemical data-->
| 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

<!-- Physical data -->
| melting_point = 310
}}

'''2C-B-FLY''' is a [[psychedelic drug|psychedelic]] and [[designer drug]] of the [[substituted phenethylamine|phenethylamine]], [[2C (psychedelics)|2C]], and [[FLY (psychedelics)|FLY]] families. It was first synthesized in 1996 by Aaron Monte, Professor of Chemistry at UW-La Crosse.<ref>{{cite web | title=Profile for Aaron Monte | website=UW-La Crosse | date=2013-04-10 | url=https://www.uwlax.edu/profile/amonte/}}</ref><ref>{{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}}</ref>

This molecule was researched by [[Alexander Shulgin]], and it was [[Ann Shulgin]]'s favorite [[research chemical]].<ref name="Kent2022">{{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.}}</ref><ref name="Cooke2021">{{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.}}</ref>

==Chemistry==
[[File:2C-B-FLY.jpg|thumb|right|2C-B-Fly in powder form]]
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 [[Drug_Enforcement_Administration|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 [[2,5-dimethoxy-4-bromoamphetamine|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." <!-- note that the "bfly/hemifly/dragonfly/butterfly/moth/gnat/flea" naming schemes are not present in the internationally peer-reviewed scientific papers reporting the invention of these compounds, but rather from internal lab references and websites such as Bluelight and Erowid. Nonetheless, these common names have been broadly and generally accepted by the designers of these compounds in order to expedite communication, and also by government agencies such as the DEA --> 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-HT<sub>2</sub> 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 "[[Psi-DOM|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.<ref name="pmid9301661">{{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 }}</ref><ref name="pmid12113827">{{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 }}</ref> The symmetrical aromatic benzodifuran derivatives tend to have the highest [[Dissociation constant#Protein-ligand binding|binding affinity]] at 5-HT<sub>2A</sub>, but the saturated benzodifuran derivatives have higher [[Intrinsic activity|efficacy]], while the saturated benzodipyran derivatives are more selective for 5-HT<sub>2C</sub>. 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.<ref name="pmid1992127">{{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}}</ref><ref name="pmid8709129">{{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}}</ref><ref>{{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 }}</ref><ref name="pmid11300881">{{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 }}</ref><ref name="pmid12150876">{{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 }}</ref><ref name="pmid12877591">{{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 }}</ref><ref name="pmid18467103">{{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}}</ref><ref>{{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 }}</ref><ref>{{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 }}</ref><ref>{{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}} }}</ref><ref>{{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 }}</ref>

[[File:Bfly structures for wiki2.png|alt=2C-BFLY and some selected analogues (SAR)|thumb|2C-BFLY and some selected analogues (SAR)]]

==Dosage==
[[Alexander Shulgin]] lists a dosage of 2C-B-FLY from 10 to 20&nbsp;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.<ref name="Erowid">{{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}}</ref>

==Pharmacology==
{| class="wikitable floatleft" style="font-size:small;"
|+ {{Nowrap|2C-B-FLY activities}}
|-
! [[Biological target|Target]] !! [[Affinity (pharmacology)|Affinity]] (K<sub>i</sub>, nM)
|-
| [[5-HT1A receptor|5-HT<sub>1A</sub>]] || 147–350
|-
| [[5-HT1B receptor|5-HT<sub>1B</sub>]] || 185
|-
| [[5-HT1D receptor|5-HT<sub>1D</sub>]] || 1.4
|-
| [[5-HT1E receptor|5-HT<sub>1E</sub>]] || 110
|-
| [[5-HT1F receptor|5-HT<sub>1F</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT2A receptor|5-HT<sub>2A</sub>]] || 11–11.6 (K<sub>i</sub>)<br />0.029–53.7 ({{Abbrlink|EC<sub>50</sub>|half-maximal effective concentration}})<br />80–104% ({{Abbrlink|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2B receptor|5-HT<sub>2B</sub>]] || 0.9 (K<sub>i</sub>)<br />0.123–40 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />56–108% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT2C receptor|5-HT<sub>2C</sub>]] || 10.6–12 (K<sub>i</sub>)<br />0.0615–0.149 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})<br />100–108% ({{Abbr|E<sub>max</sub>|maximal efficacy}})
|-
| [[5-HT3 receptor|5-HT<sub>3</sub>]] || >10,000
|-
| [[5-HT4 receptor|5-HT<sub>4</sub>]] || {{Abbr|ND|No data}}
|-
| [[5-HT5A receptor|5-HT<sub>5A</sub>]] || >10,000
|-
| [[5-HT6 receptor|5-HT<sub>6</sub>]] || 150
|-
| [[5-HT7 receptor|5-HT<sub>7</sub>]] || 606
|-
| [[Alpha-1A adrenergic receptor|α<sub>1A</sub>]] || 11,000
|-
| [[Alpha-1B adrenergic receptor|α<sub>1B</sub>]] || >10,000
|-
| [[Alpha-1D adrenergic receptor|α<sub>1D</sub>]] || {{Abbr|ND|No data}}
|-
| [[Alpha-2A adrenergic receptor|α<sub>2A</sub>]] || 145–780
|-
| [[Alpha-2B adrenergic receptor|α<sub>2B</sub>]] || 624
|-
| [[Alpha-2C adrenergic receptor|α<sub>2C</sub>]] || 233
|-
| [[Beta-1 adrenergic receptor|β<sub>1</sub>]] || >10,000
|-
| [[Beta-2 adrenergic receptor|β<sub>2</sub>]] || >10,000
|-
| [[Beta-3 adrenergic receptor|β<sub>3</sub>]] || {{Abbr|ND|No data}}
|-
| [[D1 receptor|D<sub>1</sub>]] || 1,400–4,963
|-
| [[D2 receptor|D<sub>2</sub>]] || 1,900–6,835
|-
| [[D3 receptor|D<sub>3</sub>]] || 6,800
|-
| [[D4 receptor|D<sub>4</sub>]] || >10,000
|-
| [[D5 receptor|D<sub>5</sub>]] || >10,000
|-
| [[H1 receptor|H<sub>1</sub>]] || 3,400–5,753
|-
| [[H2 receptor|H<sub>2</sub>]]–[[H4 receptor|H<sub>4</sub>]] || >10,000
|-
| [[Muscarinic acetylcholine M1 receptor|M<sub>1</sub>]] || 643
|-
| [[M2 receptor|M<sub>2</sub>]] || 2,029
|-
| [[Muscarinic acetylcholine M3 receptor|M<sub>3</sub>]] || 339
|-
| [[M4 receptor|M<sub>4</sub>]] || 520
|-
| [[M5 receptor|M<sub>5</sub>]] || 873
|-
| [[I1 receptor|I<sub>1</sub>]] || >10,000
|-
| [[Sigma-1 receptor|σ<sub>1</sub>]] || >10,000
|-
| [[Sigma-2 receptor|σ<sub>2</sub>]] || >10,000
|-
| {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || 710 (K<sub>i</sub>) (mouse)<br />30 (K<sub>i</sub>) (rat)<br />1,800 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (mouse)<br />270 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (rat)<br />>30,000 ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}}) (human)<br />49% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (mouse)<br />48% ({{Abbr|E<sub>max</sub>|maximal efficacy}}) (rat)
|-
| {{Abbrlink|SERT|Serotonin transporter}} || 10,000 (K<sub>i</sub>)<br />73,000 ({{Abbrlink|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br /> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|NET|Norepinephrine transporter}} || 17,000 (K<sub>i</sub>)<br />97,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br /> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|DAT|Dopamine transporter}} || >26,000 (K<sub>i</sub>)<br />187,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})<br /> ({{Abbr|EC<sub>50</sub>|half-maximal effective concentration}})
|-
| {{Abbrlink|MAO-A|Monoamine oxidase A}} || 19,000 ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|-
| {{Abbrlink|MAO-B|Monoamine oxidase B}} || {{Abbr|ND|No data}} ({{Abbr|IC<sub>50</sub>|half-maximal inhibitory concentration}})
|- class="sortbottom"
| colspan="2" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:''' <ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=16 March 2025 | 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= https://web.archive.org/web/20250509235235/https://d1wqtxts1xzle7.cloudfront.net/74120533/eae6c6e62565b82d46b4d111bbea0f77b9c2-libre.pdf?1635931703=&response-content-disposition=inline%3B+filename%3DIn_Vitro_Characterization_of_Psychoactiv.pdf&Expires=1746838268&Signature=Sy4fJ90yUhxs68314NxYsW5PAaNrBGePRu35WRR4PIF-3YC7Z~sLdnCn5wfqqbLg9bDEGdt~oW55ugMP3D3jgA0BoRI~~GOb0NQOwrtfUEQK1PQs1uuN9qg5Y1ct8z5NsABm44RgtukkwRMdU6fO7OlfIsQ68hOiFk129Ll7UYqldxD2f1xhE2fTTfsxSpb8cMCJzHn7-ItqLdwnAUPFK7WggDIjmY1kCnaHLwIxMwdJCAq8L6DYzSTg7pZkbR8qlou~GXbTPQt~gYpyZTJp5hgW-7V6K5wLlQ7Z2xE7B0f9wEfuc1W1QNafg125Tr-vvAe4LEGKXV58bnn1bpfWKw__&Key-Pair-Id=APKAJLOHF5GGSLRBV4ZA}}</ref>
|}

2C-B-FLY is a [[potency (pharmacology)|potent]] [[agonist]] of the [[serotonin]] [[5-HT2 receptor|5-HT<sub>2</sub> receptor]]s, including the [[serotonin]] [[5-HT2A receptor|5-HT<sub>2A</sub>]], [[serotonin]] [[5-HT2B receptor|5-HT<sub>2B</sub>]], and [[serotonin]] [[5-HT2C receptor|5-HT<sub>2C</sub> receptor]]s.<ref name="Ray2010" /><ref name="RickliKopfHoener2015" /> Unusually among [[2C drug]]s, 2C-B-FLY also shows high [[affinity (pharmacology)|affinity]] for the serotonin [[5-HT1D receptor|5-HT<sub>1D</sub> receptor]].<ref name="Ray2010" /> It also has relatively weak affinity for the serotonin [[5-HT1A receptor|5-HT<sub>1A</sub>]], [[5-HT1B receptor|5-HT<sub>1B</sub>]], and [[5-HT1E receptor|5-HT<sub>1E</sub> receptor]]s.<ref name="Ray2010" /><ref name="RickliKopfHoener2015" />

==Legality==

===Canada===
As of October 31, 2016; 2C-B-FLY is a controlled substance (Schedule III) in Canada.<ref>[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)]</ref>

===Finland===
Scheduled in the "government decree on psychoactive substances banned from the consumer market".<ref>[https://finlex.fi/fi/lainsaadanto/2014/1130 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]] 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:2C (psychedelics)]]
[[Category:5-HT2A agonists]]
[[Category:5-HT2B agonists]]
[[Category:5-HT2C agonists]]
[[Category:Alexander Shulgin]]
[[Category:Bromobenzene derivatives]]
[[Category:Designer drugs]]
[[Category:Dihydrofurans]]
[[Category:Entactogens]]
[[Category:FLY (psychedelics)]]
[[Category:Psychedelic phenethylamines]]
[[Category:Serotonin receptor agonists]]
[[Category:Substances discovered in the 1990s]]
[[Category:TAAR1 agonists]]