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'''2C-B-FLY''' is a [[psychoactive class::psychedelic]] [[chemical class::phenethylamine]] of the [[2C-x]] family which was first synthesized by Aaron P. Monte in 1996.<ref>https://erowid.org/chemicals/2cb_fly/2cb_fly_info1.shtml</ref><ref>http://www.sciencedirect.com/topics/page/2C-B-FLY</ref> It produces psychedelic and mild entactogenic effects which typically last 6–8 hours, or up to 12 hours in larger doses. It presents effects which are similar to [[2C-B]], [[mescaline]] and [[2C-D]].
Very little is known about this substance, but it gained popularity around 2005 before becoming significantly less common after two deaths occurred in October 2009 after the ingestion of a substance that was mislabeled and sold as 2C-B-FLY but was actually [[Bromo-DragonFLY]].<ref>Information on Reported Deaths Related to 2C-B-FLY | https://www.erowid.org/chemicals/2cb_fly/2cb_fly_death1.shtml</ref>
'''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>{{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>{{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.
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 and culture==
{{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>{{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}}
It has recently become easily available again through online [[research chemical]] vendors where it is being sold as a [[designer drug]].
==Chemistry==
==Chemistry==
2C-B-FLY is a substituted molecule of the [[phenethylamines|phenethylamine]] and [[benzofuran|dihydrobenzofuran]] classes of drugs. 2C-B-FLY features a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and contains a bromine atom attached to carbon R<sub>4</sub> of the phenyl ring. 2C-B-FLY 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 is a substituted molecule of the [[Substituted Phenethylamine|phenethylamine]] and [[dihydrobenzofuran]] chemical classes. 2C-B-FLY features a phenyl ring bound to an amino (NH<sub>2</sub>) group through an ethyl chain and contains a bromine atom attached to carbon R<sub>4</sub> of the phenyl 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.
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]].
==Pharmacology==
==Pharmacology==
{{Main|Serotonergic psychedelic}}
{{Further|Serotonergic psychedelic}}
2C-B-FLY's [[psychedelic]] effects are believed to come from its efficacy at the [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. It also has a high binding affinity for the 5-HT<sub>1D</sub>, 5-HT<sub>1E</sub>, 5-HT<sub>1A</sub>, 5-HT<sub>2B</sub> and 5-HT<sub>2C</sub> receptors.<ref>Psychedelics and the human receptorome. (PubMed.gov / NCBI) | https://www.ncbi.nlm.nih.gov/pubmed/20126400</ref>
2C-B-FLY is a psychedelic phenethylamine, and is the dihydrodifuran analog of 2C-B.
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 [[Serotonin#The 5-HT system|5-HT<sub>2A</sub> receptor]] as a [[Agonist#Agonists|partial agonist]]. However, the role of these interactions and how they result in the psychedelic experience remains subject to on-going scientific investigation.
However, the role of these interactions and how they result in the [[psychedelic]] experience continues to remain elusive.
==Subjective effects==
==Subjective effects==
The effects listed below are based upon the [[subjective effects index]] and personal experiences of [[PsychonautWiki]] [[Special:TopUsers|contributors]]. The listed effects will rarely (if ever) occur all at once, but heavier dosages will increase the chances and are more likely to induce a full range of 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.
In comparison to [[2C-B]], this compound presents a significantly more pronounced body high, stronger visual effects, more complex [[geometry]] and more in-depth [[internal hallucinations|hallucinations]] which are comparable to [[mescaline]], [[2C-E]] or other [[phenethylamine]] psyhedelics.
{{Preamble/SubjectiveEffects}}
===Physical effects===
The physical effects of 2C-B-FLY are comparable to that of traditional [[phenethylamines]] such as [[2C-B]], [[mescaline]] and [[2C-D]].
Many people have reported general gastrointestinal disturbances using compound which include [[diarrhoea]], [[nausea]], moderate to severe [[stomach bloating]] and general gassiness at [[moderate]] to [[heavy]] [[dosage]]s. However, it is still considerably less physically taxing and far more comfortable than other drugs in the [[2C-x]] family such as [[2C-E]] and [[2C-P]]. These effects are comparable to that of [[5-MeO-MiPT]], [[2-C-T-7]] and other compounds with highly suspected [[MAOI]]-altering properties, suggesting that 2C-B-FLY may potentially have such MAO-altering properties of its own, though this has yet to be confirmed.
{{effects/base
*'''[[Effect::Spontaneous tactile sensations]]''' - The "body high" of 2C-B-FLY can be described as a pleasurable, warm, soft, all-encompassing and mild tingling sensation. This maintains a consistent presence that steadily rises with the [[onset]] and hits its limit once the [[peak]] has been reached. It is comparable to that of a milder [[mescaline]], [[2C-B]] or [[2C-E]] experience.
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At [[light]] [[dosage]]s, this compound is generally stimulating but in a gentle, non-forceful manner similar to that of [[2C-B]] or [[mescaline]]. However, at [[heavy|heavier]] dosages one may find the amount of stimulation to increase to uncomfortable degrees if not feeling significantly sedated in a manner similar to that of [[2C-C]] or one of the many compounds in the [[2C-T]] series, most prominently [[2C-T-7]].
|{{effects/physical|
The physical effects of 2C-B-FLY are comparable to that of traditional [[Substituted Phenethylamine|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.
*'''[[Effect::Stimulation]]''' and '''[[Effect::Sedation]]''' - At [[light]] [[dosage]]s, this compound is generally stimulating but in a gentle, non-forceful manner similar to that of [[2C-B]] or [[mescaline]]. At higher dosages one may find the amount of stimulation to increase to an uncomfortable level with undertones of sedation or lethargy in a manner similar to that of [[2C-C]] or [[2C-T-7]].
*'''[[Effect::Spontaneous physical sensations]]''' - The "body high" of 2C-B-FLY can be described as a pleasurable, warm, soft, all-encompassing and mild tingling sensation. This maintains a consistent presence that steadily rises with the [[onset]] and hits its limit once the [[peak]] has been reached. It is comparable to that of a milder [[mescaline]], [[2C-B]] or [[2C-E]] experience.
**'''[[Effect::Physical euphoria]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Temperature regulation suppression]]''' - Compared to 2C-B, this effect is far more pronounced and unpredictable in its manifestation. Small increases in the dose may result in large changes in this effect.
**'''[[Effect::Increased bodily temperature]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Bodily pressures]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Headaches]]''' - This effect is more commonly reported than 2C-B or other traditional phenethylamines.
*'''[[Effect::Muscle cramps]]'''
*'''[[Effect::Stomach bloating]]'''
*'''[[Effect::Stomach cramps]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Nausea]]'''
*'''[[Effect::Bodily control enhancement]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Diarrhoea]]'''
*'''[[Effect::Dehydration]]'''
*'''[[Effect::Difficulty urinating]]'''
*'''[[Effect::Excessive yawning]]'''
*'''[[Effect::Watery eyes]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Pupil dilation]]'''
*'''[[Effect::Tactile enhancement]]'''
*'''[[Effect::Teeth grinding]]'''
*'''[[Effect::Stomach bloating]]'''
===Cognitive effects===
}}
It is worth noting that despite the potential cognitive effects of 2C-B-FLY, it 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]], [[psilocin]] or [[LSD]] due to their accompanying [[confusion]] and [[delusion]]s.
{{effects/visual|
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Creativity enhancement]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Empathy, love, and sociability enhancement]]''' - This compound presents entactogenia on a level which is less intense than that of [[2C-B]] or [[MDMA]] but similar in quality to that or [[mescaline]] or [[2C-E]].
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, intricate in appearance and unrealistic/cartoon-like in style. It is very comparable to that of [[2C-B]] or [[mescaline]].
*'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Breathing|breathing]], [[Drifting#Morphing|morphing]] and [[Drifting#Flowing|flowing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, intricate in appearance and unrealistic/cartoon-like in style. It is very comparable to that of [[2C-B]] or [[mescaline]].
*'''[[Effect::Tracers]]'''
*'''[[Effect::After images]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Colour shifting]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Depth perception distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Perspective distortions]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Symmetrical texture repetition]]'''
*'''[[Effect::Tracers]]'''
====[[Effect::Geometry]]====
====[[Effect::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 [[Geometry#Variations|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 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 [[Geometry#8B_-_Exposure_to_inner_mechanics_of_consciousness|level 8B]] visual geometry over [[Geometry#8A_-_Exposure_to_semantic_concept_network|level 8A]].
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 [[Geometry#Variations|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 [[Geometry#8B_-_Exposure_to_inner_mechanics_of_consciousness|level 8B]] visual geometry over [[Geometry#8A_-_Exposure_to_semantic_concept_network|level 8A]].
====Hallucinatory states====
====Hallucinatory states====
2C-B-FLY produces a full range of high level hallucinatory states in a fashion that is comparable to [[mescaline]] or [[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:
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:
*'''[[Effect::Transformations]]'''
*'''[[Effect::Transformations]]'''
*'''[[Effect::Internal hallucinations]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::alterations in perspective]]'' and ''[[effect::scenarios and plots]]'')
*'''[[Effect::Internal hallucination]]''' (''[[effect::autonomous entities]]''; ''[[effect::settings, sceneries, and landscapes]]''; ''[[effect::perspective hallucinations]]'' and ''[[effect::scenarios and plots]]'')
===Auditory effects===
}}
|{{effects/cognitive|
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]].
*'''[[Effect::Conceptual thinking]]'''
*'''[[Effect::Creativity enhancement]]'''
*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Emotion enhancement]]'''
*'''[[Effect::Empathy, affection, and sociability enhancement]]''' - This compound presents entactogenic effects on a level which is less intense than that of [[2C-B]] or [[MDMA]] but similar in quality to that of [[mescaline]] or [[2C-E]].
The effects which occur during the [[offset]] of this compound are comparable to that of a mild [[stimulant]]. The experience generally feels negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and may occur because of [[neurotransmitter]] depletion. Its effects commonly include:
}}
{{effects/aftereffects|
The effects which occur during the [[offset]] of this compound are comparable to that of a mild [[stimulant]] or [[entactogen]]. The experience generally feels negative and uncomfortable in comparison to the effects which occurred during its [[peak]]. This is often referred to as a "comedown" and may occur due to the physically fatiguing aspects of this substance. Its effects commonly include:
*'''[[Effect::Headaches]]'''
*'''[[Effect::Headaches]]'''
*'''[[Diarrhoea]]'''
*'''[[Effect::Diarrhea]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
}}
}}
===Experience reports===
There are currently no anecdotal reports which describe the effects of this compound within our [[experience index]]. Additional experience reports can be found here:
{{further|Research chemicals#Toxicity and harm potential|Responsible use #Hallucinogens}}
| [[File:Lolol.png|17px]]''Main articles: [[Research chemicals#Toxicity and harm potential|Research chemicals § Toxicity and harm potential]]'' ''&'' ''[[Responsible use #Hallucinogens|Responsible use § Hallucinogens]]''
The toxicity and long-term health effects of recreational 2C-B-FLY do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 2C-B-FLY is a [[research chemical]] with a very limited history of human usage.
|}
The toxicity and long-term health effects of recreational 2C-B-FLY do not seem to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. This is because 2C-B-FLY is a [[research chemical]] with very little history of human usage. Anecdotal evidence from people within the psychonaut community who have tried 2C-B-FLY suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
Anecdotal evidence from people within the community who have tried 2C-B-FLY suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
It is strongly recommended that one use [[responsible drug use|harm reduction practices]] when using this drug.
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 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.
Tolerance to the effects of 2C-B-FLY are 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===
{{Template:DangerousInteractions/Intro}}
{{DangerousInteractions/Intro}}
{{DangerousInteractions/Psychedelics}}
If 2C-B-FLY does indeed have its suspected [[MAOI]] effects, this could indicate that 2C-B-FLY is more likely to induce [[serotonin syndrome]] or general [[neurotransmitter]] overload (especially at high dosages) than other [[serotonergic psychedelic]]s.<ref>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</ref> This may make it dangerous to combine it with other [[MAOI]]s, [[stimulant]]s and certain substances which releases neurotransmitters such as [[serotonin]] or [[dopamine]]. These substances include but are not limited to:
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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*'''[[5-MeO-MiPT]]'''
*'''[[5-MeO-MiPT]]'''
*'''[[2-C-T-7]]'''
*'''[[2-C-T-7]]'''
Line 120:
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*'''[[Cocaine]]'''
*'''[[Cocaine]]'''
*'''[[Ethylphenidate]]'''
*'''[[Ethylphenidate]]'''
*'''[[Dehydroxyfluorafinil]]'''
*'''[[N-Methylbisfluoromodafinil]]'''
||
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*'''[[Isopropylphenidate]]'''
*'''[[Isopropylphenidate]]'''
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*'''[[NM-2-AI]]'''
*'''[[NM-2-AI]]'''
*'''[[Noopept]]'''
*'''[[Noopept]]'''
*'''[[SSRIs]]
*'''[[SSRIs]]'''
*'''[[SNRIs]]
*'''[[SNRIs]]'''
|}
|}
==Legal issues==
==Legal status==
{{legalStub}}
{{legalStub}}
*'''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.
*'''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 (Legislation.gov.uk) | http://www.legislation.gov.uk/ukpga/2016/2/contents/enacted</ref>
*'''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>
*'''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>
*'''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>
*'''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>
*'''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.<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>
*[http://www.bluelight.org/vb/threads/225385-The-Big-amp-Dandy-2C-B-FLY-Thread The Big & Dandy 2C-B-Fly Thread (Bluelight)]
==Literature==
*Greene, S. L. (2013). Benzofurans and benzodifurans. In Novel Psychoactive Substances (pp. 383-392). https://doi.org/10.1016/B978-0-12-415816-0.00016-X
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
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.[1]
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.[2] 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.
As a result, it may contain incomplete or wrong information. You can help by expanding it.
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.[3]
“
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 is a substituted molecule of the phenethylamine and dihydrobenzofuran chemical classes. 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.
2C-B-FLY is a psychedelic phenethylamine, and is the dihydrodifuran analog of 2C-B.
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.
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.
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWikicontributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
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.
Stimulation and Sedation - At lightdosages, this compound is generally stimulating but in a gentle, non-forceful manner similar to that of 2C-B or mescaline. At higher dosages one may find the amount of stimulation to increase to an uncomfortable level with undertones of sedation or lethargy in a manner similar to that of 2C-C or 2C-T-7.
Spontaneous physical sensations - The "body high" of 2C-B-FLY can be described as a pleasurable, warm, soft, all-encompassing and mild tingling sensation. This maintains a consistent presence that steadily rises with the onset and hits its limit once the peak has been reached. It is comparable to that of a milder mescaline, 2C-B or 2C-E experience.
Temperature regulation suppression - Compared to 2C-B, this effect is far more pronounced and unpredictable in its manifestation. Small increases in the dose may result in large changes in this effect.
Drifting(melting, breathing, morphing and flowing) - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, intricate in appearance and unrealistic/cartoon-like in style. It is very comparable to that of 2C-B or mescaline.
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:
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.
The effects which occur during the offset of this compound are comparable to that of a mild stimulant or entactogen. The experience generally feels negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and may occur due to the physically fatiguing aspects of this substance. Its effects commonly include:
There are currently no anecdotal reports which describe the effects of this compound within our experience index. Additional experience reports can be found here:
This toxicity and harm potential section is a stub.
As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. Note: Always conduct independent research and use harm reduction practices if using this substance.
The toxicity and long-term health effects of recreational 2C-B-FLY do not seem to have been studied in any scientific context and the exact toxic dose is unknown. This is because 2C-B-FLY is a research chemical with a very limited history of human usage.
Anecdotal evidence from people within the community who have tried 2C-B-FLY suggests that there are no negative health effects attributed to simply trying the drug by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed). Independent research should always be done to ensure that a combination of two or more substances is safe before consumption.
2C-B-FLY is 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 is built almost immediately after ingestion. After that, it takes about 3 days for the tolerance to be reduced to half and 7 days to be back at baseline (in the absence of further consumption). 2C-B-FLY presents cross-tolerance with [[Cross-tolerance::all psychedelics]], meaning that after the consumption of 2C-B-FLY all psychedelics will have a reduced effect.
Dangerous interactions
Warning:Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
[[Wikipedia:Lithium_(medication)|DangerousInteraction::Lithium]] - Lithium is commonly prescribed for the treatment of bipolar disorder. There is a large body of anecdotal evidence that suggests taking it with psychedelics significantly increases the risk of psychosis and seizures. As a result, this combination is strictly discouraged.
"[[UncertainInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Cannabis may have an unexpectedly strong and unpredictable synergy with the effects of 2C-B-FLY. Caution is advised with this combination as it can significantly increase the risk of adverse psychological reactions like anxiety, paranoia, panic attacks, and psychosis. Users are advised to start off with only a fraction of their normal cannabis dose and take long breaks between hits to avoid unintentional overdose.
"[[UnsafeInteraction" contains a listed "[" character as part of the property label and has therefore been classified as invalid.]] - Tramadol is well-documented to lower the seizure threshold[4] and psychedelics may act to trigger seizures in susceptible individuals.[citation needed]
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 psychedelics.[5] This may make it dangerous to combine it with MAOIs, stimulants 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:
As such, it may contain incomplete or wrong information. You can help by expanding it.
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.[6]
Germany: 2C-B-FLY is controlled under the NpSG (New Psychoactive Substances Act) as of November 26, 2016.[7][8] 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.[9]
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.[10]
Sweden: As of April 2018, 2C-B-FLY is illegal to possess, sell, buy and use under Swedish law.[11]
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.[12]
The Netherlands: 2C-B-FLY is a controlled substance as of July 1, 2025. [13]
Turkey: 2C-B-FLY is a classed as drug and is illegal to possess, produce, supply, or import.[14][15]
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.[16]
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.[17][18]
↑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. doi:10.1007/BF03161089. ISSN1556-9039.
