Chemistry:DragonFLY

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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

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 EC50 (Emax) 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

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]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "#32. DFLY". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley, CA: Transform Press. 2011. pp. 47–48. ISBN 978-0-9630096-3-0. OCLC 709667010. https://archive.org/details/shulgin-index-vol-1/page/47/mode/1up. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 "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. March 2001. doi:10.1021/jm000491y. PMID 11300881. 
  3. ↑ "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances". Quantitative Structure-Activity Relationships 18 (6): 548–560. 1999. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. http://www.erowid.org/archive/rhodium/pdf/quasi-atomistic.sar.pea.pdf. Retrieved 17 June 2025. 




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