DFMDMA
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| Clinical data | |
|---|---|
| Other names | F2-MDMA; DiFMDA; Difluoro-MDMA; 3,4-(Difluoromethylenedioxy)methamphetamine; 3,4-(Difluoromethylenedioxy)-N-methylamphetamine |
| Routes of administration | Oral[1][2] |
| ATC code |
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| Pharmacokinetic data | |
| Duration of action | Unknown[1][2] |
| Identifiers | |
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| Chemical and physical data | |
| Formula | C11H13F2NO2 |
| Molar mass | 229.227 g·mol−1 |
| 3D model (JSmol) | |
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DFMDMA, also known as F2-MDMA or as 3,4-(difluoromethylenedioxy)methamphetamine, is a chemical compound of the phenethylamine, amphetamine, and MDxx families related to the entactogen MDMA ("ecstasy").[2][3][1] It is the derivative of MDMA in which the two hydrogen atoms on the carbon atom of the 3,4-methylenedioxy ring have been replaced with fluorine atoms.[2][3][1]
Daniel Trachsel tested DFMDMA in humans and found that it was inactive at doses of up to 120 mg orally.[1][2] Higher doses were not tested.[1][2] For comparison, he listed MDMA's dose as 80 to 150 mg orally.[1]
DFMDMA was of interest as it was thought that the introduction of the fluorine atoms could prevent metabolism at the site of the methylenedioxy ring and might lower formation of neurotoxic metabolites of MDMA like 3,4-dihydroxyamphetamine (HHA; α-methyldopamine).[1][2] This in turn might improve the tolerability and safety relative to MDMA.[1][2]
The chemical synthesis of DFMDMA has been described.[3] Some notable analogues of DFMDMA include DFMDA (F2-MDA), EIDA, and IDA, among others.[1][2] DFMDA was active at the serotonin transporter (SERT) similarly to MDA and MDMA and with intermediate affinity between the two, but was inactive in humans at doses of up to 250 mg orally (whereas MDA is active at 80 to 160 mg orally).[1][2]
DFMDMA was first described in the scientific literature by Trachsel and colleagues in 2006.[3] He described its properties and effects in humans in 2012 and 2013.[1][2]
See also
[edit]References
[edit]- ^ a b c d e f g h i j k l Trachsel D (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
The first fluorinated 3,4-methylenedioxyphenethylamines described in the scientific literature were compounds 90–95, all bearing a 3,4-(difluoromethylenedioxy) moiety (Figure 6, B).[96] It was hoped that this introduction of fluorine could lower the formation of potentially neurotoxic metabolites of MDMA[96] by either blocking formation of neurotoxic a-methyldopamines via increased methylene bridge stability or formation of glutathione adducts via changing the electron density of the aromatic nucleus. Only few pharmacological characterizations have been carried out so far. Initial in vitro investigations showed DFMDA (91: Ki = 1200nM) to have a SERT affinity between that of MDA (3: Ki = 700nM) and MDMA (4: Ki = 1600nM) using a functional assay.[104] DFMDA (91) did not appear to show any activity in humans up to 250 mg, whereas MDA (3) showed its full activity at a dose of 80–160 mg.[3] The difluoro analog DFMDMA (92) was inactive at levels up to 120 mg (MDMA, 4: 80–150 mg[3]). [...] Fluorine introduction was also performed with the 3,4-methylenedioxyphenethylamines and a total of nine derivatives (90–98) were described. Monoamine transporter binding properties described so far did not elucidate the extent to which these compounds show similar neuropharmacological mechanisms of action in comparison to MDMA (4). Further work would also be required to shed more light on the impact of fluorination on the formation of potential neurotoxins.[93,95,96] What has been found so far is that human activity of DFMDA (91, >250 mg) or DFMDMA (92, >120 mg) appears to be absent which reveals that the significant properties responsible for the unique action of MDMA (4) have been changed by fluorine introduction into the 3,4-methylenedioxy bridge.
- ^ a b c d e f g h i j k 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.
- ^ a b c d Trachsel D, Hadorn M, Baumberger F (March 2006). "Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives". Chemistry & Biodiversity. 3 (3): 326–336. doi:10.1002/cbdv.200690035. PMID 17193269.