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FLY (psychedelics)

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2C-B-FLY, an example of a FLY psychedelic.
2C-B-DRAGONFLY, an example of a DragonFLY psychedelic.
2C-B-BUTTERFLY, an example of a ButterFLY psychedelic.
Examples of different FLY drugs.

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]

Examples of different types of FLY drugs, in the case of the base psychedelic 2C-B, include 2C-B-FLY, 2C-B-DRAGONFLY, 2C-B-BUTTERFLY, and 2C-B-MOTH.[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 research chemical.[8][9]

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 (but it is also orally active).[2][10] 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 18 mg for 2C-B-FLY.[11]

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

List of FLY drugs

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2C FLY drugs

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DOx FLY drugs

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25-NB FLY drugs

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Other FLY drugs

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See also

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References

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  1. ^ a b c d e 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. ^ a b c d e f 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. ^ a b c d 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.
  5. ^ a b c 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.
  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.
  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. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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. [...]
  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.
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