DFMDMA

{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = DFMDMA.svg | image_class = skin-invert-image | width = 250px | caption =

| legal_status =

| CAS_number = | CAS_supplemental = | PubChem = | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = F2-MDMA; DiFMDA; Difluoro-MDMA; 3,4-(Difluoromethylenedioxy){{shy}}methamphetamine; 3,4-(Difluoromethylenedioxy)-''N''-methylamphetamine

| IUPAC_name = 1-(2,2-difluoro-2''H''-1,3-benzodioxol-5-yl)-''N''-methylpropan-2-amine | C=11 | H=13 | F=2 | N=1 | O=2 | SMILES = CC(NC)CC1=CC(O2)=C(OC2(F)F)C=C1 | StdInChI = 1S/C11H13F2NO2/c1-7(14-2)5-8-3-4-9-10(6-8)16-11(12,13)15-9/h3-4,6-7,14H,5H2,1-2H3 | StdInChIKey = YZYZCMNVUDUELW-UHFFFAOYSA-N }}

'''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").<ref name="Trachsel_2013">{{cite book | vauthors = Trachsel D, Lehmann D, Enzensperger C | title = Phenethylamine: von der Struktur zur Funktion | location = Solothurn | year = 2013 | trans-title = Phenethylamines: From Structure to Function | edition = 1 | publisher = Nachtschatten-Verlag | series = Nachtschatten-Science | isbn = 978-3-03788-700-4 | oclc = 858805226 | url = https://books.google.com/books?id=-Us1kgEACAAJ | language = de | archive-url = https://archive.org/details/phenethylamine-von-der-struktur-zur-funktion-trachsel-lehmann-enzensperger-2013 | archive-date = 21 August 2025 }}</ref><ref name="Trachsel_2006">{{cite journal | vauthors = Trachsel D, Hadorn M, Baumberger F | title = Synthesis of fluoro analogues of 3,4-(methylenedioxy)amphetamine (MDA) and its derivatives | journal = Chemistry & Biodiversity | volume = 3 | issue = 3 | pages = 326–336 | date = March 2006 | pmid = 17193269 | doi = 10.1002/cbdv.200690035 }}</ref><ref name="Trachsel_2012">{{cite journal | vauthors = Trachsel D | title = Fluorine in psychedelic phenethylamines | journal = Drug Testing and Analysis | volume = 4 | issue = 7–8 | pages = 577–590 | date = 2012 | pmid = 22374819 | doi = 10.1002/dta.413 | quote = 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. }}</ref> 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.<ref name="Trachsel_2013" /><ref name="Trachsel_2006" /><ref name="Trachsel_2012" />

Daniel Trachsel tested DFMDMA in humans and found that it was inactive at doses of up to 120{{nbsp}}mg orally.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" /> Higher doses were not tested.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" /> For comparison, he listed MDMA's dose as 80 to 150{{nbsp}}mg orally.<ref name="Trachsel_2012" />

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).<ref name="Trachsel_2012" /><ref name="Trachsel_2013" /> This in turn might improve the tolerability and safety relative to MDMA.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" />

The chemical synthesis of DFMDMA has been described.<ref name="Trachsel_2006" /> Some notable analogues of DFMDMA include DFMDA (F2-MDA), EIDA, and IDA, among others.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" /> 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{{nbsp}}mg orally (whereas MDA is active at 80 to 160{{nbsp}}mg orally).<ref name="Trachsel_2012" /><ref name="Trachsel_2013" />

DFMDMA was first described in the scientific literature by Trachsel and colleagues in 2006.<ref name="Trachsel_2006" /> He described its properties and effects in humans in 2012 and 2013.<ref name="Trachsel_2012" /><ref name="Trachsel_2013" />

== References == {{Reflist}}

== External links == * [https://isomerdesign.com/pihkal/explore/2315 F2-MDMA (DFMDMA) - Isomer Design]

Category:Daniel Trachsel Category:Designer drugs Category:Methylenedioxyamphetamines Category:Organofluorides