DOH-FLY

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;

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]

^ ^a ^b Shulgin A, Manning T, Daley PF (2011). "#68. FLY". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 141–143. ISBN 978-0-9630096-3-0. OCLC 709667010.
^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1st ed.). Solothurn: Nachtschatten-Verlag. pp. 497–499, 515, 928–929. ISBN 978-3-03788-700-4. OCLC 858805226.
^ Cite error: The named reference Monte_1996 was invoked but never defined (see the help page).
^ ^a ^b Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE (March 2001). "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. doi:10.1021/jm000491y. PMID 11300881.