MDTFEA
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| Other names | MDTFE; MDCF3; 3,4-Methylenedioxy-N-(2,2,2-trifluoroethyl)amphetamine; N-(2,2,2-Trifluoroethyl)-3,4-methylenedioxyamphetamine |
| Routes of administration | Oral[1] |
| Drug class | Psychoactive drug |
| ATC code |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1] |
| Identifiers | |
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| PubChem CID | |
| Chemical and physical data | |
| Formula | C12H14F3NO2 |
| Molar mass | 261.244 g·mol−1 |
| 3D model (JSmol) | |
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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.[1][2][3] It is the derivative of MDEA in which the ethyl group on the amine has been replaced with a trifluoroethyl group.[1][2][3]
Alexander Shulgin briefly described MDTFEA in his book PiHKAL (Phenethylamines I Have Known and Loved).[1][3] Based on personal communication to Shulgin, it was described as "possibly active".[1] 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.[1][2][3] The effects included only a very mild intoxication and little or no sympathomimetic effects, with these possible effects being short-lasting.[1] For comparison, MDEA has a listed dose of 100 to 200 mg orally and a duration of 3 to 5 hours.[1][2][3] Daniel Trachsel has said that MDTFEA seems to be inactive.[2][3]
The chemical synthesis of MDTFEA has been described.[1]
MDTFEA was first described in the scientific literature by Shulgin in PiHKAL in 1991.[1] It was not synthesized or tested by Shulgin but was instead described to him via personal communication.[1]
See also
References
- ^ a b c d e f g h i j k l 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."
- ^ a b c d e 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.
- ^ a b c d e f 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.