2,5-Dimethoxy-4-trifluoromethylamphetamine

2,5-Dimethoxy-4-trifluoromethylamphetamine
Clinical data
Other names	2,5-Dimethoxy-4-trifluoromethylamphetamine
Legal status
Legal status	CA: Schedule I; UK: Class A;
Identifiers
	IUPAC name (RS)-1-[2,5-Dimethoxy-4-(trifluoromethyl)phenyl]propan-2-amine;
CAS Number	159277-07-3 ; 159277-12-0 (hydrochloride);
PubChem CID	10400521;
ChemSpider	8575959 ;
ChEMBL	ChEMBL6620 ;
CompTox Dashboard (EPA)	DTXSID40439330 ;
Chemical and physical data
Formula	C12H16F3NO2
Molar mass	263.260 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)c1cc(OC)c(cc1OC)CC(N)C;
	InChI InChI=1S/C12H16F3NO2/c1-7(16)4-8-5-11(18-3)9(12(13,14)15)6-10(8)17-2/h5-7H,4,16H2,1-3H3 ; Key:WPGOTSORDNBMHP-UHFFFAOYSA-N ;
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2,5-Dimethoxy-4-trifluoromethylamphetamine (DOTFM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized in 1994 by a team at Purdue University led by David E. Nichols.^[1] DOTFM is the alpha-methylated analogue of 2C-TFM, and is around twice as potent in animal studies. It acts as an agonist at the 5-HT_2A and 5-HT_2C receptors.^[1] In drug-substitution experiments in rats, DOTFM fully substituted for LSD and was slightly more potent than DOI.^[1]

References

^ ^a ^b ^c Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, Nash JF (1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT_2A/2C agonist". Journal of Medicinal Chemistry. 37 (25): 4346–4351. doi:10.1021/jm00051a011. PMID 7996545.