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TFMFly
Systematic (IUPAC) name
(2R)-1-(8-trifluoromethyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane
Identifiers
CAS number 780744-19-6
332012-20-1 (hydrochloride)
ATC code  ?
PubChem 10782206
Chemical data
Formula C 14H16F3NO2  
Mol. mass 287.277 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

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 5HT2A serotonin receptor subtype, and is a chiral compound with the more active (R) enantiomer having a Ki of 0.12nM at the human 5HT2A 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

  1. ^ Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
  2. ^ 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.  
  3. ^ 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.  
  4. ^ 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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