:TFMFly

{{Short description|Psychedelic phenethylamine drug}}

{{Drugbox

| verifiedrevid = 448234956

| IUPAC_name = (2R)-1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-amine

| image = TFMFly.svg

| width = 200

| tradename =

| legal_UK = PSA

| legal_status = Unscheduled (in general)

Illegal in Latvia

| legal_CA = Schedule I

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 780744-19-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9FHU874G42

| CAS_supplemental =
332012-20-1 (hydrochloride)

| ChemSpiderID = 8957519

| PubChem = 10782206

| ChEMBL = 1177908

| C = 14

| H = 16

| F = 3

| N = 1

| O = 2

| smiles = c13OCCc3c(C(F)(F)F)c2OCCc2c1CC(C)N

| StdInChI = 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

| StdInChIKey = KMWGSFWAZUVTCM-SSDOTTSWSA-N

}}

TFMFly is a drug related of the phenethylamine, DOx, and FLY families related to psychedelics like 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols.{{cite thesis | first = Michael Robert | last = Braden | name-list-style = vanc | degree = Ph.D. | title= Towards a biophysical understanding of hallucinogen action. | publisher = Purdue University | date = 2007 | id = {{ProQuest|304838368}} }} 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.{{cite journal | vauthors = Parrish JC, Braden MR, Gundy E, Nichols DE | title = Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists | journal = Journal of Neurochemistry | volume= 95 | issue = 6 | pages = 1575–84 | date = December 2005 | pmid = 16277614 | doi = 10.1111/j.1471-4159.2005.03477.x | s2cid = 24005602 | doi-access = free }} While the fully aromatic benzodifurans such as Bromo-DragonFLY generally have higher binding affinity than saturated compounds like 2C-B-FLY,{{cite journal | vauthors = Chambers JJ, Kurrasch-Orbaugh DM, Parker MA, Nichols DE | title = Enantiospecific synthesis and pharmacological evaluation of a series of super-potent, conformationally restricted 5-HT(2A/2C) receptor agonists | journal = Journal of Medicinal Chemistry | volume = 44 | issue = 6 | pages = 1003–10 | date = March 2001 | pmid = 11300881 | doi = 10.1021/jm000491y | citeseerx = 10.1.1.691.362 }} the saturated compounds have higher efficacy as agonists.{{cite thesis | url = http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 | first = Ralf | last = Heim | name-list-style = vanc | degree = Ph.D. | title = Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. | publisher = Freien Universität Berlin | language = German | url-access = }}