TFMFly

TFMFly
Legal status
Legal status	CA: Schedule I; UK: Under Psychoactive Substances Act; Unscheduled (in general); Illegal in Latvia
Identifiers
	IUPAC name (2R)-1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-amine;
CAS Number	780744-19-6 ; 332012-20-1 (hydrochloride);
PubChem CID	10782206;
ChemSpider	8957519;
ChEMBL	ChEMBL1177908;
CompTox Dashboard (EPA)	DTXSID10726966 ;
Chemical and physical data
Formula	C14H16F3NO2
Molar mass	287.282 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c13OCCc3c(C(F)(F)F)c2OCCc2c1CC(C)N;
	InChI InChI=1S/C14H16F3NO2/c1-7(18)6-10-8-2-4-20-13(8)11(14(15,16)17)9-3-5-19-12(9)10/h7H,2-6,18H2,1H3/t7-/m1/s1; Key:KMWGSFWAZUVTCM-SSDOTTSWSA-N;
	(verify)

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 K_i of 0.12 nM at the human 5-HT_2A receptor.^[2] While the fully aromatic benzodifurans such as Bromo-DragonFLY generally have higher binding affinity than saturated compounds like 2C-B-FLY,^[3] the saturated compounds have higher efficacy as agonists.^[4]

Legal Status

TFMFly is illegal in Latvia.^[5]

^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
^ 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. S2CID 24005602.
^ 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. CiteSeerX 10.1.1.691.362. doi:10.1021/jm000491y. PMID 11300881.
^ Heim R. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts (Ph.D. thesis) (in German). Freien Universität Berlin.
^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" [Regulations on Narcotic Drugs, Psychotropic Substances and Precursors Controlled in Latvia] (in Latvian). Ministry of Health of the Republic of Latvia. Archived from the original on 2016-02-02. Retrieved 2015-10-15.

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