TFMFly: Difference between revisions

TFMFly
Identifiers
	IUPAC name (2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane;
CAS Number	780744-19-6 ; 332012-20-1 (hydrochloride);
PubChem CID	10782206;
CompTox Dashboard (EPA)	DTXSID10726966 ;
Chemical and physical data
Formula	C14H16F3NO2
Molar mass	287.277 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c13OCCc3c(C(F)(F)F)c2OCCc2c1CC(C)N;
	(verify)

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Revision as of 07:03, 11 March 2012

TFMFly is a compound related to phenethylamine hallucinogens 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]

^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
^ Parrish JC; Braden MR; Gundy E; Nichols DE (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
^ Chambers JJ; Kurrasch-Orbaugh DM; Parker MA; Nichols DE (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. {{cite journal}}: Cite has empty unknown parameter: |author-name-separator= (help); Unknown parameter |author-separator= ignored (help); Unknown parameter |month= ignored (help)
^ 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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 | verifiedrevid = 385758973
 | IUPAC_name = (2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane