FLY (psychedelics)

Class of chemical compounds From Wikipedia, the free encyclopedia

FLY is a family of phenethylamine and benzofuran psychedelics possessing a benzodifuran or similar ring system.^[1]^[2]^[3]^[4]^[5] The FLY drugs were so-named because of the resemblance of their chemical structures to flying insects like dragonflies and butterflies.^[1]^[2]^[3]^[5] They are analogues of 2,5-dimethoxyphenethylamines in which the 2- and 5-position methoxy groups have been cyclized into furan and/or tetrahydrofuran rings.^[1]^[2]^[3] They may be 2C, DOx, 25-NB, or other FLY versions of psychedelic phenethylamines.^[1]^[2]

2C-B-DragonFLY, an example of a DragonFLY psychedelic.

Examples of different types of FLY drugs, in the case of the base psychedelic 2C-B, include 2C-B-FLY, 2C-B-DragonFLY, and 2C-B-ButterFLY, among others.^[1]^[2]^[6] BromoDragonFLY (DOB-DragonFLY) is known for its very high potency and its toxicity in overdose.^[5]^[7]^[3] 2C-B-FLY was Ann Shulgin's favorite psychedelic.^[8]^[9]^[10]^[11]

Several of the FLY drugs have been shown to act as potent serotonin 5-HT₂ receptor agonists.^[12]^[13]^[14]

Use and effects

According to Alexander Shulgin, active doses or dose ranges of FLY drugs are 2.5 to 10 mg orally for 2C-B-FLY, 1 mg orally for DOB-FLY, and 100 μg intramuscularly for Bromo-DragonFLY.^[2]^[15] Other sources provide dose ranges of 0.2 to 0.8 mg orally for Bromo-DragonFLY, 1 mg orally for DOB-FLY, and 10 to 20 mg for 2C-B-FLY.^[16]^[6]^[5] For comparison, 2C-B has a dose range of 12 to 24 mg orally while DOB has a dose range of 1 to 3 mg orally.^[1]^[2]

More information Compound, Dose ...

Oral doses and durations of FLY psychedelics
Compound	Dose	Duration
2C-B-FLY	2.5–10 mg or 10–20 mg (2–25 mg+)	Unknown
DOB-FLY	1 mg	Unknown
Bromo-DragonFLY	0.2–0.8 mg (0.2–1 mg+)	12–24 hours^a
Footnotes: ^a Bromo-DragonFLY can have a delayed onset of up to 6 hours and can have a duration of up to 2 to 3 days in some cases. Refs: ^[4]^[16]^[15]^[2] Individual: ^[6]^[7]^[17]^[18]^[19]^[5]

Interactions

History

The FLY drugs were first described in the scientific literature by Aaron Phillip Monte and David E. Nichols and colleagues at Purdue University by 1995.^[20]^[21]

List of FLY drugs

2C FLY drugs

2C-B-FLY
2C-B-ButterFLY (2C-B-MOTH)
2C-B-DragonFLY (2C-B-DFLY)
2C-B-5-hemiFLY
2C-C-FLY
2C-I-FLY
2C-DFLY (2C-H-DragonFLY; 2C-H-DFLY)
2C-D-FLY
2C-E-FLY
2C-EF-FLY
2C-T-7-FLY

DOx FLY drugs

Bromo-DragonFLY (DOB-Dragonfly; DOB-DFLY)
DOB-ANTH
DOB-FLY (3C-B-FLY)
DOB-2-DragonFLY-5-ButterFLY
DOB-5-hemiFLY (bromo-semi-FLY; B-SF)
DOB-ButterFLY (DOB-MOTH)
DOH-5-hemiFLY (semi-FLY; SF)
DOI-2-hemiFLY
DOM-FLY
DOMOM-FLY
DragonFLY (DFLY; DOH-FLY)
FLY (DOH-FLY)
TFMFly (TFM-FLY; DOTFM-FLY)

25-NB FLY drugs

2C-B-Fly-NBOMe (NBOMe-2CB-Fly)
2C-B-DragonFLY-NBOH
2C-B-FLY-NB2EtO5Cl

Cyclized FLY drugs

2C-B-5-hemiFLY-α6 (BNAP)
2CB7 (2C-B-5-hemiFLY-β7)

Other FLY drugs

Diaza-2C-DFLY
Mescaline-FLY (flyscaline)

Related compounds

9-Aminomethyl-9,10-dihydroanthracene (AMDA)
F (F-1; 5-methoxy-6-APDB)

References

[1]
Alexander T. Shulgin; Ann Shulgin (1991). PiHKAL: A Chemical Love Story (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-0-9. OCLC 25627628.
[2]
Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
[3]
Luethi D, Liechti ME (April 2020). "Designer drugs: mechanism of action and adverse effects" (PDF). Arch Toxicol. 94 (4): 1085–1133. Bibcode:2020ArTox..94.1085L. doi:10.1007/s00204-020-02693-7. PMC 7225206. PMID 32249347. The incorporation of 2'- and 5'-methoxy groups into rigid rings resulted in tetrahydrobenzodifuran and benzodifuran analogs that have been sold as designer drugs. These tetrahydrobenzodifuran and benzodifuran designer drugs are referred to as FLY and dragonFLY analogs, respectively, because of the shape of their chemical structure (Halberstadt et al. 2019; Trachsel et al. 2013)
[4]
Halberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD (January 2019). "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology. 144: 368–376. doi:10.1016/j.neuropharm.2018.10.037. PMC 6863604. PMID 30385253. DOB-DFLY is reportedly active orally in humans in the range of 0.2–0.8 mg (Trachsel et al. 2013) and has a slow onset and long duration of action, potentially lasting for up to three days. In comparison, LSD has a typical dosage range of 60–200 μg p.o. (Shulgin and Shulgin 1997). [...] 2C-B and 2C-BFLY are also essentially equipotent in humans; 2C-B-FLY is active at doses of 10–20 mg orally (Hanna et al. 2008; Green 2013) and 2C-B is active at 12–24 mg (Shulgin and Shulgin 1991). Although little is known about the human psychopharmacology of DOB-FLY, it reportedly produces hallucinogenic effects at 1 mg orally (Shulgin et al. 2011), which overlaps with the 1–3 mg effective dosage range for DOB (Shulgin and Shulgin 1991). [...]
[5]
Greene, Shaun L (2013). "Benzofurans and Benzodifurans". Novel Psychoactive Substances. Elsevier. pp. 383–392. doi:10.1016/b978-0-12-415816-0.00016-x. ISBN 978-0-12-415816-0. A typical reported dose of 2C-BFLY is 10–20mg orally [13,18].
[6]
Trachsel, D.; Lehmann, D.; Enzensperger, C. (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Das komplett aromatisierte Benzodifuran DOB-DFLY (226, auch bekannt als BromoDragonFLY oder ABDF) scheint zumindest bei Aufnahme über die Schleimhäute eine extrem potente X erbindung zu sein (die hohe Lipophilie der Verbindungkonnte die Resorption stark behindern/verzögern). So scheint 226 im Bereich von 0.2–0.8mg (200-800μg) aktiv sein, nur etwas weniger potent als LSD (50—200μg), so dass es sich auf dem Schwarzmarkt in Form von angeblichen "LSD-Trips" verbreitete [177]. Die Gefahr dabei ist dieselbe wie bei DOB (2, siehe Kapitel 8.5.10): Durch das offenbar äußerst langsame Einsetzen der Wirkung [178] (bis zu mehreren Stunden) könnte der Konsument wegen einer vermeintlichen fehlenden Wirkung oder zu tiefer Dosierung nachdosieren, was fatale Folgen haben könnte. Die Wirkdauer von DOB-DFLY (226) scheint extrem lang zu sein und kann die von LSD weit übertreffen (man spricht von 2–3 Tagen). Es gibt mehrere dokumentierte ernsthafte Vergiftungen und fatale Fälle (z.B. [178,179]). Und es gab fatale Verwechslungen: Die Opfer konsumierten vermeintlich 2C-B-FLY (388), das über einen Inernetshop vertrieben wurde, tatsächlich handelte es sich jedoch um das vielfach potentere DOB-DFLY (226) [180]. Auch gibt es Hinweise, dass DOB-DFLY (226) ein effektiver Vasokonstriktor ist, was zu Nekrose und Gangränen führen kann [178, 179, 181].
[7]
Corazza O, Schifano F, Farre M, Deluca P, Davey Z, Torrens M, Demetrovics Z, Di Furia L, Flesland L, Siemann H, Skutle A, Van Der Kreeft P, Scherbaum N (May 2011). "Designer drugs on the internet: a phenomenon out-of-control? the emergence of hallucinogenic drug Bromo-Dragonfly". Curr Clin Pharmacol. 6 (2): 125–129. doi:10.2174/157488411796151129. hdl:2299/10464. PMID 21592070.
[8]
"Godfather of Ecstasy: Alexander Shulgin's Last Trip". High Times. 10 September 2014. Retrieved 15 November 2025.
[9]
Kent, James (17 June 2022). "Remembering Psychedelic Chemist Alexander Shulgin". Psychedelic Spotlight. Retrieved 26 March 2025. 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.
[10]
Cooke, Justin (1 July 2021). "2C-B-FLY: Is It The Best Psychedelic For Arousal & Sexual Intimacy?". Tripsitter. Retrieved 26 March 2025. 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.
[11]
Sarah Hufford (2007). "An Interview with Ann Shulgin on Psychedelics and Self-Discovery" (PDF). MAPS Newsletter. 17 (2). Multidisciplinary Association for Psychedelic Studies: 23–24. In one recent case, I said often, too often, that something called 2CB Fly 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, and people were asking about it and I thought "uh-oh." It turned out that it's a disappointment to most other people. So if I say what my favorite psychedelics are, it's almost meaningless for other people, because they have to find their allies very carefully.
[12]
Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD (December 2023). "Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential". Nat Commun. 14 (1): 8221. doi:10.1038/s41467-023-44016-1. PMC 10724237. PMID 38102107.
[13]
Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015). "Pharmacological profile of novel psychoactive benzofurans". Br J Pharmacol. 172 (13): 3412–3425. doi:10.1111/bph.13128. PMC 4500375. PMID 25765500.
[14]
Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2) e9019. Bibcode:2010PLoSO...5.9019R. doi:10.1371/journal.pone.0009019. PMC 2814854. PMID 20126400.
[15]
Luethi D, Liechti ME (October 2018). "Monoamine Transporter and Receptor Interaction Profiles in Vitro Predict Reported Human Doses of Novel Psychoactive Stimulants and Psychedelics". Int J Neuropsychopharmacol. 21 (10): 926–931. doi:10.1093/ijnp/pyy047. PMC 6165951. PMID 29850881.
[16]
Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC 9191653. PMID 31917152. Table 4 Human potency data for selected hallucinogens. [...]
[17]
Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.
[18]
Hill SL, Thomas SH (October 2011). "Clinical toxicology of newer recreational drugs". Clin Toxicol (Phila). 49 (8): 705–719. doi:10.3109/15563650.2011.615318. PMID 21970769. According to user websites, a typical BromodragonFLY dose is 0.2–1 mg with an onset of action of up to 6 h and duration of action of 2 or 3 days (Psychonaut web mapping 2010).66
[19]
Matte FA, Rasmus T, Rune IB, Bente S, Mogens J (10 January 2009). "A fatal poisoning involving Bromo-Dragonfly". Forensic Science International. 183 (1): 91–96. doi:10.1016/j.forsciint.2008.11.001. PMID 19091499.
[20]
Monte AP (August 1995). Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines (Ph.D. thesis). Purdue University. Retrieved 15 April 2025.
[21]
Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE (July 1996). "Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups". J Med Chem. 39 (15): 2953–2961. doi:10.1021/jm960199j. PMID 8709129.