TFMFly

TFMFly
Systematic (IUPAC) name
	(2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane
Clinical data
Identifiers
CAS Registry Number	780744-19-6 ; 332012-20-1 (hydrochloride)
PubChem	CID 10782206
Chemical data
Formula	C14H16F3NO2
Molecular mass	287.277 g/mol
	SMILES c13OCCc3c(C(F)(F)F)c2OCCc2c1CC(C)N;
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TFMFly is a compound related to psychedelic phenethylamines such as 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols.^[1] It acts as a potent agonist at the 5HT_2A serotonin receptor subtype, and is a chiral compound with the more active (R) enantiomer having a Ki of 0.12nM at the human 5HT_2A receptor.^[2] While the fully aromatic benzodifurans such as bromodragonfly generally have higher binding affinity than saturated compounds like 2C-B-FLY,^[3] the saturated compounds have higher efficacy as agonists.^[4]

References[edit]

^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
^ Parrish JC; Braden MR; Gundy E; Nichols DE (December 2005). "Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists". Journal of Neurochemistry 95 (6): 1575–84. doi:10.1111/j.1471-4159.2005.03477.x. PMID 16277614.
^ 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): 1003–10. doi:10.1021/jm000491y. PMID 11300881.
^ Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)

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