DOH-FLY
DOH-FLY, also known simply as FLY or H-FLY, is a serotonin receptor agonist of the phenethylamine, DOx, and FLY families. It is the "FLY" analogue of 2,5-dimethoxyamphetamine.
Pharmacology
The enantiomers of FLY, -FLY and -FLY, show affinity and activity at the serotonin 5-HT2 receptors. At the serotonin 5-HT2A receptor, the affinity of -FLY was 54.4nM and of -FLY was 227nM, while at the serotonin 5-HT2C receptor, the affinity of -FLY was 8.2nM and of -FLY was 119nM. In terms of activational potency at the serotonin 5-HT2A receptor, the of -FLY was 5,650nM while that of -FLY was 2,360nM. The enantiomers of FLY have greater activity as serotonin 5-HT2A receptor agonists than -2,5-DMA but show dramatically lower potency than 4-substituted FLY analogues like DOB-FLY. In other studies, the affinity of racemic FLY for the serotonin 5-HT2A receptor was 2,010nM, relative to 15 to 18nM for DOB-FLY, 0.23nM for Bromo-DragonFLY, and 5,200nM for 2,5-DMA.FLY was included and described as an entry in Alexander Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. It partially substituted for LSD in rodent drug discrimination tests, with a maximal substitution of 64% at a dose of 4.0mmol/kg. The drug was markedly less potent in these tests than 4-substituted analogues like DOB-FLY. The pharmacokinetics of FLY in rats have been studied. 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.