MDDMA

{{For|the opioid known as 6-MDDM|6-Methylenedihydrodesoxymorphine}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424887836 | drug_name = | image = MDDM structure.svg | image_class = skin-invert-image | width = 225px | image2 = MDDM ball-and-stick structure.png | image_class2 = bg-transparent | width2 = 250px

| legal_status =

| CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 74698-50-3 | CAS_supplemental = | PubChem = 551630 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 479880 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = L6K8DR1S8O | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 3,4-Methylenedioxy-''N'',''N''-dimethylamphetamine; 3,4-Methylenedioxy-(α,''N'',''N''-trimethyl)-1-ethane; MDDM; MDDMA; ''N'',''N''-Dimethyl-MDA; ''N''-Methyl-MDMA

| IUPAC_name = 1-(2''H''-1,3-benzodioxol-5-yl)-''N'',''N''-dimethylpropan-2-amine | C=12 | H=17 | N=1 | O=2 | SMILES = CC(Cc1ccc2c(c1)OCO2)N(C)C | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C12H17NO2/c1-9(13(2)3)6-10-4-5-11-12(7-10)15-8-14-11/h4-5,7,9H,6,8H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = JEJGUIDNYBAPGN-UHFFFAOYSA-N

| melting_point = 172 | melting_high = 173 }}

'''MDDMA''', or '''MDDM''', also known as '''3,4-methylenedioxy-''N'',''N''-dimethylamphetamine''' or as '''''N'',''N''-dimethyl-MDA''' or '''''N''-methyl-MDMA''', is a psychoactive drug of the phenethylamine, amphetamine, and MDxx families.<ref name="PiHKAL">{{CitePiHKAL}} https://erowid.org/library/books_online/pihkal/pihkal105.shtml</ref><ref name="SandtnerStocknerHasenhuetl2016" /><ref name="VargasHatzipantelisDunlap2026">{{cite journal | vauthors = Vargas MV, Hatzipantelis CJ, Dunlap LE, Tombari RJ, Avanes AA, Vaillancourt S, Llorach P, Salgado JS, Heifets BD, Olson DE | title = R-MDDMA is a Safer Analogue of MDMA with Therapeutic Potential | journal = ACS Chem Neurosci | volume = | issue = | pages = | date = April 2026 | pmid = 42010927 | doi = 10.1021/acschemneuro.5c00891 | url = }}</ref> It is the ''N'',''N''-dimethyl analogue of MDA and the ''N''-methyl derivative of MDMA.<ref name="PiHKAL" /> The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.<ref name="ByrskaMasierStanaszek2025">{{cite journal | vauthors = Byrska B, Masier K, Stanaszek R | title = "New kid on the block"-MDDM as a new ingredient in Ecstasy tablets | journal = J Forensic Sci | volume = | issue = | pages = | date = November 2025 | pmid = 41254475 | doi = 10.1111/1556-4029.70226 | url = }}</ref> In addition, (''R'')-MDDMA was characterized as a non-hallucinogenic psychoplastogen with antidepressant-like effects and improved safety relative to MDMA in 2026.<ref name="VargasHatzipantelisDunlap2026" />

==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists MDDMA's dose as greater than 150{{nbsp}}mg orally and its duration as unknown.<ref name="PiHKAL" /> Findings on the effects of MDDMA are very mixed.<ref name="PiHKAL" /> In two reports, with 150{{nbsp}}mg and 1,000{{nbsp}}mg both orally, no effects whatsoever occurred.<ref name="PiHKAL" /> In another report, 550{{nbsp}}mg orally resulted in very negative effects.<ref name="PiHKAL" /> Finally, two people who used 200{{nbsp}}mg orally found that it produced very pleasant effects for 20{{nbsp}}minutes, wore off, but then resurged to produce even stronger effects 4{{nbsp}}hours later.<ref name="PiHKAL" /> The higher-dose reports were communicated to Shulgin anonymously and he was uncertain whether the actual substance employed was indeed MDDMA.<ref name="PiHKAL" /> More research seems necessary to characterize MDDMA, but Shulgin expected that a "pretty hefty dose" would be required for it to produce effects.<ref name="PiHKAL" />

==Pharmacology== ===Pharmacodynamics=== MDDMA shows reduced potency as a monoamine releasing agent and reuptake inhibitor compared to MDA and MDMA.<ref name="SandtnerStocknerHasenhuetl2016">{{cite journal | vauthors = Sandtner W, Stockner T, Hasenhuetl PS, Partilla JS, Seddik A, Zhang YW, Cao J, Holy M, Steinkellner T, Rudnick G, Baumann MH, Ecker GF, Newman AH, Sitte HH | title = Binding Mode Selection Determines the Action of Ecstasy Homologs at Monoamine Transporters | journal = Mol Pharmacol | volume = 89 | issue = 1 | pages = 165–175 | date = January 2016 | pmid = 26519222 | pmc = 4702095 | doi = 10.1124/mol.115.101394 | url = }}</ref> It was 11-fold less potent than MDMA and 4-fold less potent than MDA as a serotonin releasing agent (SRA).<ref name="SandtnerStocknerHasenhuetl2016" /> Moreover, whereas MDA and MDMA are serotonin–norepinephrine–dopamine releasing agents (SNDRAs), MDDMA is a selective SRA along with ≥10-fold weaker dopamine and norepinephrine reuptake inhibition.<ref name="SandtnerStocknerHasenhuetl2016" /> The related drug MDTMA is completely inactive as a monoamine releasing agent, though it does still show very weak monoamine reuptake inhibition.<ref name="SandtnerStocknerHasenhuetl2016" /> Another related drug, dimethylamphetamine, is said to be a prodrug of methamphetamine and amphetamine, although it is much less potent and weaker than these drugs.<ref name="DettmeyerVerhoff2013">{{cite book| vauthors = Dettmeyer R, Verhoff MA, Schütz HF |title=Forensic Medicine: Fundamentals and Perspectives|url=https://books.google.com/books?id=yHHABAAAQBAJ&pg=PA519|date=9 October 2013|publisher=Springer Science & Business Media|isbn=978-3-642-38818-7|page=519 | quote = Table 30.13: Amphetamine Data [...] ''Note:'' So-called prodrugs, such as amphetaminil (psychoanaleptic), benzphetamine, clobenzorex, dimethylamphetamine, ethylamphetamine, famprofazone, fencamine, fenethylline, fenproporex, furfenorex, mefenorex, mesocarb, prenylamine, and selegiline (antiparkinson agent), can result in the production of methamphetamine or amphetamine in the organism}}</ref><ref name="Cody2002">{{cite journal | vauthors = Cody JT | title = Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results | journal = J Occup Environ Med | volume = 44 | issue = 5 | pages = 435–450 | date = May 2002 | pmid = 12024689 | doi = 10.1097/00043764-200205000-00012 | url = }}</ref><ref name="InoueSuzuki1987">{{cite journal | vauthors = Inoue T, Suzuki S | title = The metabolism of dimethylamphetamine in rat and man | journal = Xenobiotica | volume = 17 | issue = 8 | pages = 965–971 | date = August 1987 | pmid = 3673111 | doi = 10.3109/00498258709044195 | url = }}</ref>

(''R'')-MDDMA has been found be inactive as a serotonin releasing agent but to act as a partial agonist of the serotonin 5-HT2A and 5-HT2C receptors.<ref name="VargasHatzipantelisDunlap2026" /> Conversely, unlike MDMA, it was inactive as a serotonin 5-HT2B receptor agonist.<ref name="VargasHatzipantelisDunlap2026" /> In animal studies, (''R'')-MDDMA did not produce the head-twitch response, affect body temperature, or induce hyperlocomotion, and showed diminished or no prosocial effects.<ref name="VargasHatzipantelisDunlap2026" /> On the other hand, it produced psychoplastogenic effects mediated by serotonin 5-HT2 receptor activation as well as promoted fear extinction and induced antidepressant-like effects.<ref name="VargasHatzipantelisDunlap2026" /> It was concluded that (''R'')-MDDMA is a non-hallucinogenic psychoplastogen with improved safety compared to MDMA and (''R'')-MDMA.<ref name="VargasHatzipantelisDunlap2026" />

===Pharmacokinetics=== It is possible that MDDMA could be partially demethylated into MDMA.<ref name="VargasHatzipantelisDunlap2026" /> However, based on (''R'')-MDDMA and (''R'')-MDMA having very different effects in animals, such conversion appears to be limited.<ref name="VargasHatzipantelisDunlap2026" />

==Chemistry== ===Synthesis=== The chemical synthesis of MDDMA has been described.<ref name="PiHKAL" />

===Impurity=== MDDMA is occasionally encountered as an impurity in MDMA which has been synthesized by methylation of MDA using methylating chemical reagents such as methyl iodide. An excess of reagent or a reaction temperature that is too high results in some double methylation of the amine nitrogen, yielding MDDMA as well as MDMA. The presence of MDDMA as an impurity can thus reveal which synthetic route was used to manufacture seized samples of MDMA.<ref name="CasteeleBoucheBocxlaer2005">{{cite journal | vauthors = Casteele SR, Bouche MP, Van Bocxlaer JF | title = LC-MS/MS in the elucidation of an isomer of the recreational drug methylenedioxy ethylamphetamine: methylenedioxy dimethylamphetamine | journal = Journal of Separation Science | volume = 28 | issue = 14 | pages = 1729–1734 | date = September 2005 | pmid = 16224967 | doi = 10.1002/jssc.200500108 }}</ref><ref name="DeLetterLambertBouche2007">{{cite journal | vauthors = De Letter EA, Lambert WE, Bouche MP, Cordonnier JA, Van Bocxlaer JF, Piette MH | title = Postmortem distribution of 3,4-methylenedioxy-N,N-dimethyl-amphetamine (MDDM or MDDA) in a fatal MDMA overdose | journal = International Journal of Legal Medicine | volume = 121 | issue = 4 | pages = 303–307 | date = July 2007 | pmid = 16636864 | doi = 10.1007/s00414-006-0094-x }}</ref><ref name="AwadBelalMaher2010">{{cite journal | vauthors = Awad T, Belal T, Maher HM, DeRuiter J, Clark CR | title = GC-MS studies on side chain regioisomers related to substituted methylenedioxyphenethylamines: MDEA, MDMMA, and MBDB | journal = Journal of Chromatographic Science | volume = 48 | issue = 9 | pages = 726–732 | date = October 2010 | pmid = 20875234 | doi = 10.1093/chromsci/48.9.726 }}</ref>

===Analogues=== Analogues of MDDMA include MDA, MDMA, MDTMA (''N'',''N'',''N''-trimethyl-MDA) and dimethylone (βk-MDDMA), among others.<ref name="PiHKAL" />

==History== MDDMA was first described in the scientific literature by Alexander Shulgin and colleagues by 1980.<ref name="BraunShulginBraun1980">{{cite journal | vauthors = Braun U, Shulgin AT, Braun G | title = Centrally active N-substituted analogs of 3,4-methylenedioxyphenylisopropylamine (3,4-methylenedioxyamphetamine) | journal = J Pharm Sci | volume = 69 | issue = 2 | pages = 192–195 | date = February 1980 | pmid = 6102141 | doi = 10.1002/jps.2600690220 | url = }}</ref> Subsequently, it was described in greater detail by Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" /> The drug was described as a possible novel designer drug in 2025.<ref name="ByrskaMasierStanaszek2025" /> David E. Olson and colleagues characterized (''R'')-MDDMA as a non-hallucinogenic psychoplastogen with antidepressant-like effects and improved safety relative to MDMA in 2026.<ref name="VargasHatzipantelisDunlap2026" />

==Society and culture== ===Legal status=== ====Canada==== MDDMA is a controlled substance in Canada.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>

====United Kingdom==== This substance is a Class A drug in the Drugs controlled by the UK Misuse of Drugs Act.<ref>{{cite web | title = UK Misuse of Drugs act 2001 Amendment summary | url = http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | access-date = 12 March 2014 | publisher = Isomer Design | archive-date = 22 October 2017 | archive-url = https://web.archive.org/web/20171022085110/http://isomerdesign.com/Cdsa/scheduleUK.php?schedule=1&ion=30&structure=C | url-status = dead }}</ref>

==Research== (''R'')-MDDMA may have therapeutic potential with improved safety compared to MDMA.<ref name="VargasHatzipantelisDunlap2026" />

== References == {{Reflist}}

== External links == * [https://isomerdesign.com/pihkal/explore/105 MDDM (MDDMA) - Isomer Design] * [http://www.erowid.org/library/books_online/pihkal/pihkal105.shtml MDDM - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/105 MDDM - PiHKAL - Isomer Design]

Category:5-HT2A agonists Category:5-HT2C agonists Category:Designer drugs Category:Dimethylamino compounds Category:Methamphetamines Category:Methylenedioxyamphetamines Category:PiHKAL Category:Psychoplastogens Category:Serotonin releasing agents