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DOH-FLY

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Not to be confused with FLY (psychedelics).

DOH-FLY
Clinical data
Other namesFLY; H-FLY; HFLY
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 1-(2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H17NO2
Molar mass219.284 g·mol−1
3D model (JSmol)
  • CC(CC1=C2C(=CC3=C1CCO3)CCO2)N
  • InChI=1S/C13H17NO2/c1-8(14)6-11-10-3-5-15-12(10)7-9-2-4-16-13(9)11/h7-8H,2-6,14H2,1H3
  • Key:QTMQYHDNFFQCRI-UHFFFAOYSA-N

DOH-FLY, also known simply as FLY or H-FLY, is a serotonin receptor agonist of the phenethylamine, DOx, and FLY families.[1][2][3][4] It is the "FLY" (benzodidihydrofuran) analogue of 2,5-dimethoxyamphetamine (2,5-DMA or DOH).[1][4]

Pharmacology

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The enantiomers of FLY, (R)-FLY and (S)-FLY, show affinity and activity at the serotonin 5-HT2 receptors.[1][4] At the serotonin 5-HT2A receptor, the affinity (Ki) of (R)-FLY was 54.4 nM and of (S)-FLY was 227 nM, while at the serotonin 5-HT2C receptor, the affinity (Ki) of (R)-FLY was 8.2 nM and of (S)-FLY was 119 nM.[4] In terms of activational potency at the serotonin 5-HT2A receptor, the EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) of (R)-FLY was 5,650 nM (99%) while that of (S)-FLY was 2,360 nM (62%).[4] The enantiomers of FLY have greater activity as serotonin 5-HT2A receptor agonists than (R)-2,5-DMA but show dramatically lower potency than 4-substituted FLY analogues like DOB-FLY.[4] In other studies, the affinity (Ki) of racemic FLY for the serotonin 5-HT2A receptor was 2,010 nM, relative to 15 to 18 nM for DOB-FLY, 0.23 nM for Bromo-DragonFLY, and 5,200 nM for 2,5-DMA.[3][5]

FLY was included and described as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1] It partially substituted for LSD in rodent drug discrimination tests, with a maximal substitution of 64% at a dose of 4.0 mmol/kg.[3] The drug was markedly less potent in these tests than 4-substituted analogues like DOB-FLY.[3] The pharmacokinetics of FLY in rats have been studied.[6] FLY is not known to have been assessed in humans, and hence it is unknown whether FLY has psychedelic or other psychoactive effects in humans.[1]

History

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FLY was first described in the scientific literature by 1995.[1][3][7] It was not an explicitly controlled substance in the United States as of 2011.[1]

See also

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References

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  1. ^ a b c d e f g Shulgin A, Manning T, Daley PF (2011). "#68. FLY". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 141–143. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1st ed.). Solothurn: Nachtschatten-Verlag. pp. 497–499, 515, 928–929. ISBN 978-3-03788-700-4. OCLC 858805226.
  3. ^ a b c d e 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". Journal of Medicinal Chemistry. 39 (15): 2953–2961. doi:10.1021/jm960199j. PMID 8709129.
  4. ^ a b c d e f Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE (March 2001). "Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists". Journal of Medicinal Chemistry. 44 (6): 1003–1010. doi:10.1021/jm000491y. PMID 11300881.
  5. ^ Parker MA, Kurrasch DM, Nichols DE (April 2008). "The role of lipophilicity in determining binding affinity and functional activity for 5-HT2A receptor ligands". Bioorganic & Medicinal Chemistry. 16 (8): 4661–4669. doi:10.1016/j.bmc.2008.02.033. PMC 2442558. PMID 18296055.
  6. ^ Baralla E, Nieddu M, Burrai L, Varoni MV, Demontis MP, Boatto G (May 2019). "LC-MS/MS analysis of two new designer drugs (FLY serie) in rat plasma and its application to a pharmacokinetic study". Legal Medicine. 38. Tokyo, Japan: 58–63. doi:10.1016/j.legalmed.2019.04.004. PMID 30991226.
  7. ^ Monte AP (1995). "Structure-activity relationships of hallucinogens: Design, synthesis, and pharmacological evaluation of a series of conformationally restricted phenethylamines". Purdue e-Pubs. Archived from the original on 16 June 2025.
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