DOH-FLY
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
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| Other names | FLY; H-FLY; HFLY |
| Drug class | Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist |
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| Formula | C13H17NO2 |
| Molar mass | 219.284 g·mol−1 |
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Pharmacology
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 EC50 (Emax) 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
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]