TFMFly

TFMFly
Clinical data
Other names	TFM-FLY; TFM-Fly; DOTFM-FLY
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
Legal status
Legal status	CA: Schedule I; UK: Under Psychoactive Substances Act; Unscheduled (in general); Illegal in Latvia
Identifiers
	IUPAC name 1-[4-(trifluoromethyl)-2,3,6,7-tetrahydrofuro[2,3-f][1]benzofuran-8-yl]propan-2-amine;
CAS Number	780744-19-6 Y ; 332012-20-1 (hydrochloride);
PubChem CID	57507897;
ChemSpider	57566595;
UNII	9FHU874G42;
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 CC(CC1=C2CCOC2=C(C3=C1OCC3)C(F)(F)F)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; Key:KMWGSFWAZUVTCM-UHFFFAOYSA-N;
	(verify)

TFMFly, or TFM-FLY, also known as DOTFM-FLY, is a serotonin receptor modulator of the phenethylamine, amphetamine and DOx, and FLY families related to psychedelics like DOTFM and DOB-FLY.¹²³

Pharmacology

Pharmacodynamics

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,¹ the saturated compounds have higher efficacy as agonists.⁴

Chemistry

Synthesis

The chemical synthesis of TFMFly has been described.¹

Analogues

Analogues of TFMFly include DOTFM, DOB-FLY, and 25TFM-NBOMe, among others.

History

TFMFly was first reported by a team at Purdue University led by David E. Nichols in 2001.¹³

Society and culture

Legal status

Latvia

TFMFly is illegal in Latvia.⁵

References

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". J Med Chem. 44 (6): 1003–1010. doi:10.1021/jm000491y. PMID 11300881.
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): 1575–1584. doi:10.1111/j.1471-4159.2005.03477.x. PMID 16277614. S2CID 24005602.
Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.
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.

External links

TFM-FLY - Isomer Design

[ChambersKurrasch-OrbaughParker2001-1] 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". J Med Chem. 44 (6): 1003–1010. doi:10.1021/jm000491y. PMID 11300881.

[ParrishBradenGundy2005-2] 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): 1575–1584. doi:10.1111/j.1471-4159.2005.03477.x. PMID 16277614. S2CID 24005602.

[Braden2007-3] Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. ProQuest 304838368.

[4] 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.

[5] "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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