{"Abbreviation":["MDMA"],"Absorption, Distribution and Excretion":"renal","Aliases":["3,4-Methylenedioxymethamphetamine","MDMA","Ecstasy","Midomafetamine","42542-10-9","Methylenedioxymethamphetamine","(3,4-Methylenedioxy)methamphetamine","N-methyl-3,4-methylenedioxyamphetamine","3,4-(methylenedioxy)methamphetamine","N,α-Dimethyl-1,3-benzodioxole-5-ethanamine","midomafetamina","KE1SEN21RM","Methylenedioxymetamphetamine","Methylenedioxymethamfetamine","CHEBI:1391","1,3-Benzodioxole-5-ethanamine, N,α-dimethyl-","3,4-methylenedioxymetamphetamine","Phenethylamine, N,α-dimethyl-3,4-methylenedioxy-","3,4-Methylenedioxy-N,α-dimethyl-β-phenylethylamine","N-Methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane","Mandy","Molly","XTC","[1-(2H-1,3-benzodioxol-5-yl)propan-2-yl](methyl)amine","midomafetaminum","(1-(2H-1,3-benzodioxol-5-yl)propan-2-yl)(methyl)amine","N Methyl 3,4 methylenedioxyamphetamine","Hydrochloride, N-Methyl-3,4-methylenedioxyamphetamine","980-806-5","HSDB 6929","MANDY","DEA No. 7405","N-Methyl-3,4-(methylenedioxy)amphetamine","1-(1,3-Benzodioxol-5-yl)-N-methyl-2-propanamine","Chembl43048","Ncgc00168266-02","Unii-ke1sen21rm","CCRIS 9277","rac-3,4-Methylenedioxymethamphetamine-D5","Epitope ID:178091","Schembl44210","Methylenedioxy Methamphetamine","DivK1c_000962","3,4-MDMA","GTPL4574","Schembl29353930","KBio1_000962","Dtxsid90860791","Ninds_000962","BDBM707600","LFA76543","RCA14289","Bdbm50010588","Pdsp1_001522","Pdsp2_001506","3,4-methylenedioxy-n-methylamphetamine","Akos006283463","DB01454","Idi1_000962","Ncgc00168266-01","D,l-3,4-methylenedioxymethamphetamine","NS00010441","C07577","D11172","Q69488","1-(2H-1,3-Benzodioxol-5-yl)-N-methylpropan-2-amine","Phenethylamine, n,α-dimethyl-3,4-methylenedioxy-","1-(Benzo(d)(1,3)dioxol-5-yl)-n-methylpropan-2-amine","N,α-dimethyl-3,4-(methylenedioxy)phenethylamine","N-methyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane","rac-MDMA (rac-3,4-Methylenedioxymethamphetamine) 1.0 mg/ml in Methanol"],"Biological Half-Life":"6–10 (though duration of effects is typically actually 3–5 hours)","Boiling Point":"BP: 100-110 °C at 0.4 mmHg","CAS":"42542-10-9","ChemicalClasses":["amphetamine","methylenedioxyphenethylamine"],"Chirality":"racemic","Color/Form":"Oil","Drug Indication":"Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.","DurationOfAction":"3 – 6 hours","EliminationHalfLife":"| (R)-MDMA|(''R'')-MDMA: 11 (range 5.1 – 24) hours}-}","Esters":[],"European Community (EC) Number":"980-806-5","Formating":[],"HMDB ID":"HMDB0254382","HeavyAtomCount":14,"Human Drugs":"Pharmaceuticals","IUPACName":"1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine","InChI":"InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3","InChIKey":"SHXWCVYOXRDMCX-UHFFFAOYSA-N","Interactions":"The effects of injection of 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and N-ethyl-3,4-methylenedioxyamphetamine (MDEA) (all 20 mg/kg) on blood pressure, heart rate, core body temperature and locomotor activity in conscious rats were investigated using radiotelemetry. MDMA and MDA produced a prolonged increase in both systolic and diastolic pressures, with MDA causing the most marked rise. MDEA produced a transient but nonsignificant fall in diastolic pressure. The pressor response produced by MDA was accompanied by bradycardia. All three amphetamine derivatives caused an initial hypothermic response; however, MDA also produced a subsequent hyperthermia, and the speed of recovery from hypothermia was MDA\u003eMDMA\u003eMDEA. The alpha-2A-adrenoceptor antagonist 2-((4,5-dihydro-1H-imidazol-2-yl)methyl)-2,3-dihydro-1-methyl-1H-isoindole (BRL 44408) (1 mg/kg) prolonged the hypothermic response to MDMA. Only MDA induced locomotor activity when given alone, but in the presence of BRL 44408, MDMA produced increased locomotor activity. The order of potency for producing isometric contractions of rat aorta (alpha1D) and vas deferens (alpha1A) was MDA\u003eMDMA\u003eMDEA, with MDEA acting as an alpha1-adrenoceptor antagonist with a pKB of 4.79 +/- 0.12 (n=4) in aorta. The order of potency for prejunctional inhibition of stimulation-evoked contractions in rat vas deferens (alpha2A-adrenoceptor mediated) was MDA\u003eMDMA\u003eMDEA. Blood pressure actions of the three amphetamine derivatives may be at least partly due to alpha1-adrenoceptor agonism or antagonism. The reversal of the hypothermic actions are at least partly due to alpha2A-adrenoceptor agonism since the hypothermic response was more prolonged with MDEA which exhibits low alpha2A-adrenoceptor potency, and effects of MDMA after alpha2A-adrenoceptor antagonism were similar to those of MDEA.","MeSH Pharmacological Classification":"Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.","Mechanism of Action":"It enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylation. It also acts as a weak 5-HT1 and 5-HT2 receptor agonist. MDMA's unusual entactogenic effects have been hypothesized to be, at least partly, the result of indirect oxytocin secretion via activation of the serotonin system. Oxytocin is a hormone released following events like hugging, orgasm, and childbirth, and is thought to facilitate bonding and the establishment of trust. Based on studies in rats, MDMA is believed to cause the release of oxytocin, at least in part, by both directly and indirectly agonizing the serotonin 5-HT1A receptor.","Metabolism/Metabolites":"Midomafetamine, or MDMA, is reported to undergo extensive CYP-mediated hepatic metabolism, with CYP2D6 playing a major role in humans. Other CYP enzymes contributing to MDMA metabolism are CYP3A4 and COMT.  MDMA is metabolized via two primary metabolic pathways. It may undergo O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation. In contrast, it may also undergo N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. Due to autoinhibition of CYP2D6 and CYP2D8, MDMA displays a complex, nonlinear pharmacokinetics profile, with the zeroth order kinetics occurring at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.","MolecularFormula":"C\u003csub\u003e11\u003c/sub\u003eH\u003csub\u003e15\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"193.24 g/mol","Non-Human Toxicity Values":"LD50 Mouse ip 97 mg/kg /MDMA hydrochloride/","Opticalactivity":"( + / - )","Pharmacodynamics":"MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.","PubChemId":1615,"Record Description":["LiverTox|CNS|Stimulant|Sympathomimetic amine","Wikipedia|PiHKAL|Phenethylamines"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"6368","RefCount":4,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/MDMA","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q69488","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB01454","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/1615","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=42542-10-9","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0254382","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C07577","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/KE1SEN21RM","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID90860791","Name":"3,4-Methylenedioxymethamphetamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 1615, 3,4-Methylenedioxymethamphetamine. Accessed January 22, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/1615\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/1615\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 3,4-Methylenedioxymethamphetamine. UNII: KE1SEN21RM. Global Substance Registration System. Accessed January 22, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/KE1SEN21RM\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/KE1SEN21RM\u003c/a\u003e","Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed January 22, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003c/a\u003e"],"Reported Fatal Dose":"The toxic dose is variable, with near fatal and fatal ingestions having been reported with blood levels between 0.11 mg/L to 2.1 mg/L. Survival has also been reported after MDMA blood levels of 4.3 mg/L drawn 13 hours after ingestion.","SMILES":"CC(CC1=CC2=C(C=C1)OCO2)NC","SaltData":[{"AcidCount":1,"Amine":"3,4-Methylenedioxymethamphetamine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 127.639 39.997\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#1ff01f\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h128v40H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M77.296 31.331v-15.24M77.296 16.091l-13.198-7.62M64.098 8.471 50.9 16.091\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M50.9 16.091 37.697 8.462M48.462 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substance"},{"gov":"New Zealand","ref":[],"schedule":"Class B substance"},{"gov":"United Kingdom","ref":[],"schedule":"Class A substance"},{"act":"Controlled Substances Act (CSA)","gov":"United States","ref":[],"schedule":"Schedule I"},{"gov":"United Nations","ref":[],"schedule":"Schedule I substance"},{"gov":"European Union","ref":[],"schedule":"Fully prohibited substance"}],"Slang":["Mandy ","Molly ","XTC "],"Stability/Shelf Life":"Stable under recommended storage conditions. /(+/-)-3,4-Methylenedioxymethamphetamine hydrochloride/","StereoisomerData":[],"StereoisomerType":"enantiomer","Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 104.731 39.997\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" 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