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2C-B-FLY: Difference between revisions
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'''2C-B-FLY''' is a lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] and [[chemical class::benzodihydrodifuran]] classes that produces an array of [[psychedelic]] and [[entactogenic]] effects when [[Route of administration|administered]]. 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 lesser-known novel [[psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] and [[chemical class::benzodihydrodifuran]] classes that produces an array of [[psychedelic]] and [[entactogenic]] effects when [[Route of administration|administered]]. 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.<ref>https://erowid.org/chemicals/2cb_fly/2cb_fly_info1.shtml | 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.<ref>{{Citation | title=Erowid 2C-B-Fly Vaults : 2C-B-FLY | url=https://erowid.org/chemicals/2cb_fly/2cb_fly_info1.shtml}}</ref> | ||
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.<ref> | 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.<ref>{{Citation | title=Erowid 2C-B-Fly Vault: Death Reports 2009 | url=https://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml}}</ref> 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. | 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. | ||
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==History and culture== | ==History and culture== | ||
{{historyStub}} | {{historyStub}} | ||
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.<ref> | 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.<ref>{{cite journal | journal=MAPS | title=An Interview with Ann Shulgin on Psychedelics and Self-Discovery | volume=17 | issue=2 | pages=23–24 | date= 2007 | url=https://maps.org/news-letters/v17n2/v17n2_annshulgin-23.pdf}}</ref> | ||
{{quote3|text=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.|author=Ann Shulgin}} | {{quote3|text=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.|author=Ann Shulgin}} | ||
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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 R<sub>2</sub> and R<sub>5</sub> of 2C-B into five-member dihydrofuran rings fused to the central benzene 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 R<sub>2</sub> and R<sub>5</sub> 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]]. | 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]]. | ||
==Pharmacology== | ==Pharmacology== | ||
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{{Preamble/SubjectiveEffects}} | {{Preamble/SubjectiveEffects}} | ||
{{effects/base | {{effects/base | ||
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*'''[[Effect::Diarrhea]]''' | *'''[[Effect::Diarrhea]]''' | ||
*'''[[Effect::Dehydration]]''' | *'''[[Effect::Dehydration]]''' | ||
*'''[[Effect::Difficulty urinating]]''' | |||
*'''[[Effect::Excessive yawning]]''' | *'''[[Effect::Excessive yawning]]''' | ||
*'''[[Effect::Watery eyes]]''' | *'''[[Effect::Watery eyes]]''' | ||
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It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this substance. | ||
===Tolerance and addiction potential=== | ===Tolerance and addiction potential=== | ||
2C-B-FLY is [[Addiction potential::not habit-forming]] and the desire to use it can actually decrease with use. It is most often self-regulating. | 2C-B-FLY is [[Addiction potential::not habit-forming]], and the desire to use it can actually decrease with use. It is most often self-regulating. | ||
Tolerance to the effects of 2C-B-FLY | Tolerance to the effects of 2C-B-FLY is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). 2C-B-FLY presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of 2C-B-FLY all psychedelics will have a reduced effect. | ||
===Dangerous interactions=== | ===Dangerous interactions=== | ||
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{{DangerousInteractions/Psychedelics}} | {{DangerousInteractions/Psychedelics}} | ||
If 2C-B-FLY does have suspected MAO-altering effects, this could indicate that 2C-B-FLY is more likely to induce [[serotonin syndrome]] or general [[monoamine]] overload (especially at high dosages) than other [[serotonergic psychedelic]]s.<ref>Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: | If 2C-B-FLY does have suspected MAO-altering effects, this could indicate that 2C-B-FLY is more likely to induce [[serotonin syndrome]] or general [[monoamine]] overload (especially at high dosages) than other [[serotonergic psychedelic]]s.<ref>{{cite journal | vauthors=((Gallardo-Godoy, A.)), ((Fierro, A.)), ((McLean, T. H.)), ((Castillo, M.)), ((Cassels, B. K.)), ((Reyes-Parada, M.)), ((Nichols, D. E.)) | journal=Journal of Medicinal Chemistry | title=Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors: Biological Activities, CoMFA Analysis, and Active Site Modeling | volume=48 | issue=7 | pages=2407–2419 | date=1 April 2005 | url=https://pubs.acs.org/doi/10.1021/jm0493109 | issn=0022-2623 | doi=10.1021/jm0493109}}</ref> This may make it dangerous to combine it with [[MAOI]]s, [[stimulant]]s and certain substances which modulate synaptic concentrations of neurotransmitters such as [[serotonin]], [[dopamine]] and [[norepinephrine]] through unknown mechanisms. These substances include but are not limited to: | ||
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{{legalStub}} | {{legalStub}} | ||
*'''Austria''': 2C-B-FLY is illegal to possess, produce and sell under the NPSG. (Neue-Psychoaktive-Substanzen-Gesetz Österreich). | *'''Austria''': 2C-B-FLY is illegal to possess, produce and sell under the NPSG. (Neue-Psychoaktive-Substanzen-Gesetz Österreich).{{citation needed}} | ||
*'''Canada''': 2C-B-FLY would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>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</ref> | *'''Canada''': 2C-B-FLY would be considered Schedule III as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>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</ref> | ||
*'''Germany''': 2C-B-FLY is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> 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.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | *'''Germany''': 2C-B-FLY is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016.<ref>{{cite web|url=https://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl116s2615.pdf#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl116s2615.pdf%27%5D__1576017393518|title=Gesetz zur Bekämpfung der Verbreitung neuer psychoaktiver Stoffe|publisher=Bundesanzeiger Verlag|access-date=December 11, 2019|language=de}}</ref><ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/anlage.html|title=Anlage NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> 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.<ref>{{cite web|url=https://www.gesetze-im-internet.de/npsg/__4.html|title=§ 4 NpSG|publisher=Bundesministerium der Justiz und für Verbraucherschutz|access-date=December 11, 2019|language=de}}</ref> | ||
*'''Sweden''': As of April 2018, 2C-B-FLY is illegal to possess, sell, buy and use under Swedish law.<ref>https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/ | *'''Italy''': 2C-B-FLY is a schedule I substance and is illegal to possess, produce, sell and buy.{{citation needed}} | ||
*'''Poland''': 2C-B-FLY is unscheduled in Poland. However, it would be considered in Group II-P drug as it is a derivative of 2,5-dimethoxyphenethylamine.<ref>{{cite web|url=https://sip.lex.pl/akty-prawne/dzu-dziennik-ustaw/wykaz-substancji-psychotropowych-srodkow-odurzajacych-oraz-nowych-18747849|title=Wykaz substancji psychotropowych, środków odurzających oraz nowych substancji psychoaktywnych|access-date=5 June, 2024|language=pl}}</ref> | |||
*'''Sweden''': As of April 2018, 2C-B-FLY is illegal to possess, sell, buy and use under Swedish law.<ref>{{Citation | title=Nyhetsarkiv — Folkhälsomyndigheten | url=https://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/}}</ref> | |||
*'''Switzerland''': It is unclear whether 2C-B-FLY is in the scope of a substituted phenethylamine under Verzeichnis E point 130, since it is not an "alkyl, alkoxy, alkylenedioxy or halide derivative of phenethylamine", while additionally containing further univalent substituents, according to the scope. Although it could theoretically be considered an alkoxy derivative, it would still miss one hydrogen atom on the alkyl part of the alkoxy substituent. It is also unclear if it can be considered a true ether analog of an ether analog of 2C-B which would make it controlled under Buchstabe C.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | *'''Switzerland''': It is unclear whether 2C-B-FLY is in the scope of a substituted phenethylamine under Verzeichnis E point 130, since it is not an "alkyl, alkoxy, alkylenedioxy or halide derivative of phenethylamine", while additionally containing further univalent substituents, according to the scope. Although it could theoretically be considered an alkoxy derivative, it would still miss one hydrogen atom on the alkyl part of the alkoxy substituent. It is also unclear if it can be considered a true ether analog of an ether analog of 2C-B which would make it controlled under Buchstabe C.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref> | ||
*'''The Netherlands''' | *'''The Netherlands:''' 2C-B-FLY is a controlled substance as of July 1, 2025. <ref>{{Citation|title= Bepaalde groepen designerdrugs (ook wel nieuwe psychoactieve stoffen) zijn sinds 1 juli 2025 verboden. Deze stoffen zijn schadelijk. Gebruikers kunnen er gezondheidsproblemen van krijgen en er zelfs door overlijden. | year=2025|url=https://www.rijksoverheid.nl/onderwerpen/drugs/verbod-op-designerdrugs}}</ref> | ||
*'''Turkey:''' 2C-B-FLY is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf</ref> | *'''Turkey:''' 2C-B-FLY is a classed as drug and is illegal to possess, produce, supply, or import.<ref name="Bakanlar Kurulu Kararı - Karar Sayısı : 2013/5742">https://resmigazete.gov.tr/eskiler/2014/01/20140125-3.htm</ref> <ref name="List of illegal substances for law"> https://resmigazete.gov.tr/eskiler/2014/01/20140125-3-1.pdf</ref> | ||
*'''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.<ref>Psychoactive Substances Act 2016 | *'''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.<ref>{{Citation | title=Psychoactive Substances Act 2016 | url=https://www.legislation.gov.uk/ukpga/2016/2/contents/enacted}}</ref> | ||
*'''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. | *'''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.<ref>Drug control: Highlights of P.L. 99-570, Anti Drug Abuse Act of 1986: (drug-related provisions only) (1986). bill.</ref><ref>"[https://www.deadiversion.usdoj.gov/schedules/orangebook/e_cs_sched.pdf#page=1 Controlled Substances: by CSA Schedule]" (PDF). U.S. Department of Justice. November 18, 2021. p. 1.</ref> | ||
==See also== | ==See also== | ||
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[[Category:Psychedelic]] | [[Category:Psychedelic]] | ||
[[Category:Research chemical]] | [[Category:Research chemical]] | ||
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