DOH-FLY

Not to be confused with FLY (psychedelics).

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]

DOH-FLY

Clinical data
Other names	FLY; H-FLY; HFLY
Drug class	Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 1-(2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-4-yl)propan-2-amine
CAS Number	219986-80-8
PubChem CID	10608911
ChemSpider	8784278
ChEMBL	ChEMBL99846
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=C2C(=CC3=C1CCO3)CCO2)N
InChI 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

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-HT_2A receptor, the affinity (K_i) of (R)-FLY was 54.4 nM and of (S)-FLY was 227 nM, while at the serotonin 5-HT_2C receptor, the affinity (K_i) of (R)-FLY was 8.2 nM and of (S)-FLY was 119 nM.^[4] In terms of activational potency at the serotonin 5-HT_2A receptor, the EC₅₀Tooltip half-maximal effective concentration (E_maxTooltip 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-HT_2A 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 (K_i) of racemic FLY for the serotonin 5-HT_2A 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]

See also

• Substituted methoxyphenethylamine
• FLY (psychedelics)
• Substituted benzofuran
• DragonFLY (DFLY)