DOH-FLY

Clinical data
Other names	FLY; H-FLY; HFLY
Drug class	Serotonin receptor agonist;Serotonin5-HT2A receptoragonist
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
PubChemCID	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

DOH-FLY, also known simply asFLY orH-FLY, is aserotonin receptor agonist of thephenethylamine,DOx, andFLY families.^[1][2][3][4] It is the "FLY" (benzodidihydrofuran)analogue of2,5-dimethoxyamphetamine (2,5-DMA or DOH).^[1][4]

Theenantiomers of FLY, (R)-FLY and (S)-FLY, showaffinity and activity at theserotonin5-HT₂ receptors.^[1][4] At the serotonin5-HT_2A receptor, the affinity (K_i) of (R)-FLY was 54.4 nM and of (S)-FLY was 227 nM, while at the serotonin5-HT_2C receptor, the affinity (K_i) of (R)-FLY was 8.2 nM and of (S)-FLY was 119 nM.^[4] In terms ofactivationalpotency at the serotonin 5-HT_2A receptor, theEC₅₀Tooltip 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 likeDOB-FLY.^[4] In other studies, the affinity (K_i) ofracemic FLY for the serotonin 5-HT_2A receptor was 2,010 nM, relative to 15 to 18 nM for DOB-FLY, 0.23 nM forBromo-DragonFLY, and 5,200 nM for 2,5-DMA.^[3][5]

FLY was included and described as an entry inAlexander Shulgin's 2011 bookThe Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.^[1] It partially substituted forLSD in rodentdrug 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] Thepharmacokinetics 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 haspsychedelic or otherpsychoactive effects in humans.^[1]

FLY was first described in thescientific literature by 1995.^[1][3][7] It was not an explicitlycontrolled substance in theUnited States as of 2011.^[1]

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

• DOH-FLY - Isomer Design

• Drugs not assigned an ATC code
• 5-HT2A agonists
• Benzofurans
• FLY (psychedelics)
• Heterocyclic compounds with 3 rings
• Psychedelic phenethylamines
• Serotonin receptor agonists
• Secondary amines

• CS1 German-language sources (de)
• CS1 maint: bot: original URL status unknown
• Articles with short description
• Short description matches Wikidata
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Articles without UNII source
• Drugs with no legal status
• Articles containing unverified chemical infoboxes