TFMFly

TFMFly
Legal status
Legal status	CA: Schedule I ; UK: Class A ;
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;
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;
	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 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]

Legal Status

TFMFly is illegal in Latvia.[5]

References

Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.
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.
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.
Ralf Heim PhD. Synthese und Pharmakologie potenter 5-HT2A-Rezeptoragonisten mit N-2-Methoxybenzyl-Partialstruktur. Entwicklung eines neuen Struktur-Wirkungskonzepts. (German)
Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem

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[1] Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.

[pmid16277614-2] 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.

[pmid11300881-3] 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. CiteSeerX 10.1.1.691.362. 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)

[5] Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem