TFMFly: Difference between revisions

| verifiedrevid = 385758973

| IUPAC_name = (2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane

| image = TFMFly_structure.png

| width = 200

<!--Clinical data-->

| tradename =

<!--Identifiers-->

| CAS_number = 780744-19-6

| CAS_supplemental = </br>332012-20-1 (hydrochloride)

| PubChem = 10782206

<!--Chemical data-->

| C=14 | H=16 | F=3 | N=1 | O=2

| molecular_weight = 287.277 g/mol

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

'''TFMFly''' is a compound related to [[phenethylamine]] [[psychedelic|hallucinogen]]s such as [[2C-B-FLY]] and [[2C-TFM]]. It was first reported in 2005 by a team at [[Purdue University]] led by [[David Nichols]].<ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref> It acts as a potent [[agonist]] at the [[5HT2A receptor|5HT_2A]] [[serotonin]] [[Receptor (biochemistry)|receptor]] subtype, and is a [[Chirality (chemistry)|chiral]] compound with the more active (R) [[enantiomer]] having a Ki of 0.12nM at the human 5HT_2A receptor.<ref name="pmid16277614">{{cite journal |title=Differential phospholipase C activation by phenylalkylamine serotonin 5-HT 2A receptor agonists |journal=Journal of Neurochemistry |volume=95 |issue=6 |pages=1575–84 |year=2005 |month=December |pmid=16277614 |doi=10.1111/j.1471-4159.2005.03477.x |url= |author1=Parrish JC |author2=Braden MR |author3=Gundy E |author4=Nichols DE |author-separator=, |author-name-separator=}}</ref> While the fully aromatic benzodifurans such as [[bromodragonfly]] generally have higher [[Dissociation constant#Protein-ligand binding|binding affinity]] than saturated compounds like 2C-B-FLY,<ref name="pmid11300881">{{cite journal |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 |year=2001 |month=March |pmid=11300881 |doi= 10.1021/jm000491y|url= |author1=Chambers JJ |author2=Kurrasch-Orbaugh DM |author3=Parker MA |author4=Nichols DE |author-separator=, |author-name-separator=}}</ref> the saturated compounds have higher [[Intrinsic activity|efficacy]] as agonists.<ref>[http://www.diss.fu-berlin.de/diss/receive/FUDISS_thesis_000000001221 Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)]</ref>

==References==

[[Category:Benzodifurans]]

[[Category:Organofluorides]]