2,5-Dimethoxy-4-trifluoromethylamphetamine

2,5-Dimethoxy-4-trifluoromethylamphetamine
Clinical data
Other names	2,5-Dimethoxy-4-trifluoromethylamphetamine; 4-Trifluoromethyl-2,5-dimethoxyamphetamine; DOTFM; 3C-TFM
Routes of; administration	Oral
Legal status
Legal status	CA: Schedule I; UK: Class A;
Pharmacokinetic data
Duration of action	Unknown
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 ;
UNII	NLH3FWZ9T4;
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 ;
	(verify)

2,5-Dimethoxy-4-trifluoromethylamphetamine (DOTFM) is a psychedelic drug of the phenethylamine, amphetamine, and DOx (where 'x' indicates a 4-substitution on the phenyl group of 2,5-dimethoxyamphetamine) families. It was first synthesized in 1994 by a team at Purdue University led by David E. Nichols.^[3] DOTFM is the α-methylated analogue of 2C-TFM. It is the most potent DOx psychedelic.^[1]^[2]

^ ^a ^b ^c Cite error: The named reference Trachsel2012 was invoked but never defined (see the help page).
^ ^a ^b ^c Cite error: The named reference TrachselLehmannEnzensperger2013 was invoked but never defined (see the help page).
^ Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, et al. (December 1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist". Journal of Medicinal Chemistry. 37 (25): 4346–4351. doi:10.1021/jm00051a011. PMID 7996545.

[Trachsel2012-1] Cite error: The named reference Trachsel2012 was invoked but never defined (see the help page).

[TrachselLehmannEnzensperger2013-2] Cite error: The named reference TrachselLehmannEnzensperger2013 was invoked but never defined (see the help page).

[pmid7996545-3] Nichols DE, Frescas S, Marona-Lewicka D, Huang X, Roth BL, Gudelsky GA, et al. (December 1994). "1-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)-2-aminopropane: a potent serotonin 5-HT2A/2C agonist". Journal of Medicinal Chemistry. 37 (25): 4346–4351. doi:10.1021/jm00051a011. PMID 7996545.

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