MDTFEA

MDTFEA
Clinical data
Other namesMDTFE; MDCF3; 3,4-Methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine; N-(2,2,2-Trifluoroethyl)-3,4-methylenedioxyamphetamine
Routes of
administration		Oral
Drug classPsychoactive drug
ATC code
  • None
Pharmacokinetic data
Duration of actionUnknown
Identifiers
  • 1-(1,3-benzodioxol-5-yl)-N-(2,2,2-trifluoroethyl)propan-2-amine
PubChem CID
Chemical and physical data
FormulaC12H14F3NO2
Molar mass261.244 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C=C1)OCO2)NCC(F)(F)F
  • InChI=1S/C12H14F3NO2/c1-8(16-6-12(13,14)15)4-9-2-3-10-11(5-9)18-7-17-10/h2-3,5,8,16H,4,6-7H2,1H3
  • Key:MWFPHJXMCQTNGG-UHFFFAOYSA-N

MDTFEA, also known as 3,4-methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine, is a chemical compound and possible psychoactive drug of the phenethylamine, amphetamine, and MDxx families related to the entactogen MDEA. It is the derivative of MDEA in which the ethyl group on the amine has been replaced with a trifluoroethyl group.

Alexander Shulgin briefly described MDTFEA in his book PiHKAL (Phenethylamines I Have Known and Loved). Based on personal communication to Shulgin, it was described as "possibly active". The drug was tested at a highest total dose of 500 mg orally, which was given in three divided doses over a period of 5 or 6 hours. The effects included only a very mild intoxication and little or no sympathomimetic effects, with these possible effects being short-lasting. For comparison, MDEA has a listed dose of 100 to 200 mg orally and a duration of 3 to 5 hours. Daniel Trachsel has said that MDTFEA seems to be inactive.

The chemical synthesis of MDTFEA has been described.

MDTFEA was first described in the scientific literature by Shulgin in PiHKAL in 1991. It was not synthesized or tested by Shulgin but was instead described to him via personal communication.

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "I have been told of an analogue of MDE that has been synthesized, and explored by the researcher who synthesized it. It contains the N-trifluoroethyl group common to several pharmaceuticals such as Quazepam. The analogue is 3,4-methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine hydrochloride (mp 207–209 °C) which was made from 2,2,2-trifluoroethylamine and 3,4-methylenedioxyphenylacetone and sodium cyanoborohydride in methanol. The best final line for this compound is that it is “possibly active.” The most heroic dosage schedule mentioned was a total of 500 milligrams, taken in three approximately equal portions over the course of five or six hours, with only a very mild intoxication and little or no sympathomimetic effects. And what little there might have been was quickly gone."
  2. 1 2 3 4 5 Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819. The N-trifluoroethyl analogue 17 of amphetamine has also been described.[43] Apparently, this derivatization of amphetamine (1) leads to almost complete loss of the stimulating properties. The same N-substituent has been introduced into the well known derivative 3,4-methylenedioxyamphetamine (MDA, 3), an entactogenic, stimulating and psychedelic compound.[3] Only investigated in humans so far, 3,4-methylenedioxy-N-trifluoroethylamphetamine (MDTFEA, 18) seems to be inactive up to 500 mg[3] while its fluorine-free analog MDEA (5) is a well known entactogen and active in the range of 100–200 mg with a duration of 3–5 h.[3] While steric effects might play a role it has been shown that an N-trifluoroethyl derivative loses its amine properties and that this group was used successfully as a bioisostere to replace an amide group.[11] Amide analogs of psychoactive phenethylamines are generally considered to be inactive in humans.[44,45] Similar electronic effects might apply to derivatives 11 and 13.
  3. 1 2 3 4 5 6 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.