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DragonFLY

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From Wikipedia, the free encyclopedia

DragonFLY
Clinical data
Other namesDFLY; H-DFLY
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 1-furo[2,3-f][1]benzofuran-4-ylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H13NO2
Molar mass215.252 g·mol−1
3D model (JSmol)
  • CC(CC1=C2C(=CC3=C1C=CO3)C=CO2)N
  • InChI=1S/C13H13NO2/c1-8(14)6-11-10-3-5-15-12(10)7-9-2-4-16-13(9)11/h2-5,7-8H,6,14H2,1H3
  • Key:RZXKDUYUWHJRCH-UHFFFAOYSA-N

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

Pharmacology

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The enantiomers of DFLY, (R)-DFLY and (S)-DFLY, show affinity and activity at the serotonin 5-HT2 receptors.[1][2] At the serotonin 5-HT2A receptor, the affinity (Ki) of (R)-DFLY was 1.5 nM and of (S)-DFLY was 37.9 nM, while at the serotonin 5-HT2C receptor, the affinity (Ki) of (R)-DFLY was 0.79 nM and of (S)-DFLY was 6.0 nM.[2] In terms of activational potency at the serotonin 5-HT2A receptor, the EC50Tooltip half-maximal effective concentration (EmaxTooltip maximal efficacy) of (R)-DFLY was 590 nM (76%) while that of (S)-DFLY was 650 nM (68%).[2] The enantiomers of DFLY have far greater activity as serotonin 5-HT2A receptor agonists than (R)-2,5-DMA but show dramatically lower potency than 4-substituted FLY analogues like Bromo-DragonFLY.[2]

DFLY was included and described as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1] However, it is not known to have been assessed in animals or humans, and hence it is unknown whether DFLY has psychedelic or other psychoactive effects in humans.[1]

History

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DFLY was first described in the scientific literature by at least 1999.[1][2][3] It was not an explicitly controlled substance in the United States as of 2011.[1]

Society and culture

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Canada

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DragonFLY is a controlled substance in Canada under phenethylamine blanket-ban language.[4]

See also

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References

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  1. 1 2 3 4 5 6 7 Shulgin A, Manning T, Daley PF (2011). "#32. DFLY". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 47–48. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. 1 2 3 4 5 6 7 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.
  3. ↑ Kovar KA, Vedani A, Schulze-Alexandru M (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances" (PDF). Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. Retrieved 17 June 2025.
  4. ↑ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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