{"Abbreviation":["MDA"],"Absorption, Distribution and Excretion":"... This paper describes for the first time an evaluation of the concentrations of methylenedioxymethamphetamine (MDMA) and 3,4-methylenedioxyamphetamine (MDA) found in five fatalities admitted to hospital where both antemortem and postmortem blood samples were available. Admission MDMA and MDA concentrations ranged between 0.55 and 4.33 mg/L and 0 and 0.10 mg/L, respectively, in antemortem serum/plasma. Postmortem blood MDMA and MDA concentrations ranged between 0.47 and 28.39 mg/L and 0.02 and 1.33 mg/L, respectively. Postmortem concentrations were higher than corresponding antemortem concentrations in all 5 cases with postmortem/antemortem ratios between 1.1 and 6.6 for MDMA and 1.5 and 13.3 for MDA. Differences in concentrations were also observed between anatomical sites, with central sites (e.g., heart) having much higher concentrations than peripheral sites (e.g., femoral). Overall, MDMA and MDA appear to exhibit postmortem redistribution and concentrations measured in postmortem specimens (even from peripheral sites) are not directly comparable with antemortem findings close to or prior to death.","Aliases":["Tenamfetamine","Methylenedioxyamphetamine","Tenamfetaminum","Love","methylene dioxyamphetamine","1,3-Benzodioxole-5-ethanamine, α-methyl-","α-Methyl-1,3-benzodioxole-5-ethanamine","Tenanfetamina","EA-1299","α-Methyl-3,4-(methylenedioxy)phenethylamine","1-(2H-1,3-benzodioxol-5-yl)propan-2-amine","3,4 Methylenedioxyamphetamine","3,4-Methylenedioxy-amphetamine","MDA","Brn 0150196","DEA No. 7400","AI3-24882","Mda","CHEMBL6731","51497-09-7","5-19-08-00417","Phenethylamine, α-methyl-3,4-(methylenedioxy)-","3,4-(Methylenedioxy)amphetamine","α-Methyl-3,4-methylenedioxyphenethylamine","Tenamfetamina","Ncgc00168264-01","MDA,R(-)","Unii-xjz28fj27w","HSDB 7593","Dtxsid40859958","3-(1,3-benzodioxol-5-yl)-1,1,1,2,3-pentadeuteriopropan-2-amine","SKF-5","DivK1c_000964","Schembl393456","MDA,","Schembl29392330","KBio1_000964","Chebi:166520","Ninds_000964","Bdbm50005247","Pdsp1_001410","Pdsp2_001394","(R,S)-3,4-Methylenedioxyamphetamine","5-(2-Aminopropyl)-1,3-benzodioxole","Akos002433952","DB01509","Idi1_000964","DB-290498","DS-015925","1-(3,4-Methylenedioxyphenyl)-2-propylamine","NS00010421","2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine","D12715","benzene, 1-(2-amino)propyl-3,4-methylenedioxy-","(-)2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine","3,4-(Methylenedioxy)-α-methylphenylethylamine","(+/-)2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine","3,4-methylenedioxy-α-methyl-β-phenylethylamine","α-Methyl-3,4-(methylenedioxy)phenylethylamine","(-)-2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine","(+)-2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine","1,3-Benzodioxole,5-ethanamine-α-methyl-(.+/-.)","2-Benzo[1,3]dioxol-5-yl-1-methyl-ethylamine((R)-(-)-MDA)","rac-MDA (rac-3,4-Methylenedioxyamphetamine) 1.0 mg/ml in Methanol"],"Boiling Point":"157 °C","CAS":"4764-17-4","Chemical Classes":"Stimulant","ChemicalClasses":["3,4-methylenedioxyphenethylamine","amphetamine"],"Chirality":"racemic","Classes":["Entactogen","Stimulant"],"Color/Form":"Almost colorless oil","DBI-IGS":["MDA","MDA"],"Decomposition":"When heated to decomposition it emits toxic fumes of /Nitrogen oxides/.","Dosing Info":[{"Method":"Oral","Tiers":{"Common":{"Entries":2,"Lower":118.8,"Percentage":50,"Unit":"mg","Upper":150},"Extreme":{"Entries":1,"Lower":157,"Percentage":25,"Unit":"mg","Upper":157},"Heavy":{"Entries":0,"Lower":152.5,"Percentage":0,"Unit":"mg","Upper":157},"Light":{"Entries":1,"Lower":118.8,"Percentage":25,"Unit":"mg","Upper":118.8},"Strong":{"Entries":0,"Lower":150,"Percentage":0,"Unit":"mg","Upper":152.5}}}],"DurationOfAction":"5 – 8 hours (range 1 – 10 hours)\u003ca href='#cite_note-4'\u003e\u003csup\u003e[4]\u003c/sup\u003e\u003c/a\u003e","EliminationHalfLife":"8.4 – 10.9 hours","Erowid Experience Reports":[{"Author":"Ob","Id":65820,"Title":"Way Below Expected Effect"},{"Author":"ALLROY1420","Id":66332,"Title":"A Little Vacation"},{"Author":"Siren","Id":67160,"Title":"I Felt Really Connected to the World"},{"Author":"Indelibleface","Id":67831,"Title":"These Aren't Toys We Play With"},{"Author":"Jay C.","Id":69193,"Title":"It's A Beautiful Life"},{"Author":"love_rabb1t","Id":70275,"Title":"Rave Pollenation"},{"Author":"Tripper","Id":70839,"Title":"Tended to Make Me Very Sociable"},{"Author":"Number 6","Id":71031,"Title":"Snowball at the Millenium"},{"Author":"go ask alice","Id":72571,"Title":"Wanted! Our Kidnapped Serotonin (Reward)"},{"Author":"Vaya","Id":76766,"Title":"Stimulating Sensuality"},{"Author":"k4rnage","Id":81050,"Title":"Love Comes From the Source"},{"Author":"still tired","Id":44469,"Title":"All Extremes of What Emotion has to Offer"},{"Author":"SmokingMan","Id":65756,"Title":"Supergroovalisticprosifunkstication"},{"Author":"Sam","Id":65671,"Title":"Never Had a 'Negative' Effect"},{"Author":"B-20","Id":45802,"Title":"Weird Trip"},{"Author":"Cactushead","Id":46747,"Title":"Kills the Effects of MD*"},{"Author":"mUnk","Id":85960,"Title":"The Teaching Tool"},{"Author":"A Pagan God","Id":47596,"Title":"Drawings In the Sky"},{"Author":"Amethyst Deceiver","Id":49142,"Title":"A Glowing Christmas Eve"},{"Author":"Plex","Id":56031,"Title":"I Miss It Like My Best Friend"},{"Author":"SomeoneLikeMyself","Id":56160,"Title":"Brain Reset Body Reborn"},{"Author":"KidWithTheJaw","Id":56213,"Title":"Slowly but Surely"},{"Author":"Particle Man","Id":57488,"Title":"Colour Bleed, and a Good Swim"},{"Author":"bohemian","Id":62888,"Title":"Gentle, Pleasant and Easy"},{"Author":"Bun","Id":82417,"Title":"Beauty's Rebirth"},{"Author":"Bun","Id":82430,"Title":"Love at First Sassy"}],"Esters":[],"European Community (EC) Number":"803-951-7","Formating":[],"HMDB ID":"HMDB0041931","HeavyAtomCount":13,"Human Drugs":"Pharmaceuticals","IUPACName":"1-(1,3-benzodioxol-5-yl)propan-2-amine","InChI":"InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3","InChIKey":"NGBBVGZWCFBOGO-UHFFFAOYSA-N","Interactions":"Designer drugs of the amphetamine type (eg, ... MDA) ... have gained popularity and notoriety as rave drugs. ... A variety of adverse effects have been associated with the use/abuse of this class of drugs in humans, including a life-threatening serotonin syndrome, hepatotoxicity, neurotoxicity, and psychopathology.","KEGG Entries":[{"Id":"D12715","Interactions":[],"Synonyms":["Tenamfetamine","3,4-Methylenedioxyamphetamine","MDA"]},{"Id":"D12715","Interactions":[],"Synonyms":["Tenamfetamine","3,4-Methylenedioxyamphetamine","MDA"]},{"Id":"D12715","Interactions":[],"Synonyms":["Tenamfetamine","3,4-Methylenedioxyamphetamine","MDA"]}],"MeSH Headers":[{"Id":"M0023232","Link":"https://id.nlm.nih.gov/mesh/M0023232.html","Name":"3,4-Methylenedioxyamphetamine","Ref":94},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":96},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":112},{"Id":"M0009763","Link":"https://id.nlm.nih.gov/mesh/M0009763.html","Name":"Hallucinogens","Ref":113},{"Id":"M0027732","Link":"https://id.nlm.nih.gov/mesh/M0027732.html","Name":"Serotonin Agents","Ref":114},{"Id":"M0028095","Link":"https://id.nlm.nih.gov/mesh/M0028095.html","Name":"Adrenergic Uptake Inhibitors","Ref":115}],"MeSH Pharmacological Classification":[{"Id":"M0009763","Link":"https://id.nlm.nih.gov/mesh/M0009763.html","Name":"Hallucinogen","Ref":113},{"Id":"M0027732","Link":"https://id.nlm.nih.gov/mesh/M0027732.html","Name":"Serotonin Agent","Ref":114},{"Id":"M0028095","Link":"https://id.nlm.nih.gov/mesh/M0028095.html","Name":"Adrenergic Uptake Inhibitor","Ref":115}],"Mechanism of Action":"Phenylethylamines act on the peripheral and central nervous system by alpha- and beta-adrenergic stimulation. These compounds may also have varying degrees of serotonergic and dopaminergic activity, depending on structural similarity to mescaline. /Phenylethylamines/","Metabolism/Metabolites":"The phase I and II metabolites of the designer drugs methylenedioxyamphetamine (MDA), R,S-methylenedioxymethamphetamine (MDMA), R,S-methylenedioxyethylamphetamine (MDE), R, S-benzodioxazolylbutanamine (BDB) and R, S-N-methyl-benzodioxazolylbutanamine (MBDB) were identified by gas chromatography-mass spectrometry (GC-MS) or liquid chromotography-mass spectrometry (LC-MS) in urine and liver microsomes of humans and rats. Two overlapping pathways could be postulated: (1) demethylenation followed by catechol-O-methyl-transferase (COMT) catalyzed methylation and/or glucuronidation/sulfatation; (2) N-dealkylation, deamination and only for MDA, MDMA, MDE oxidation to the corresponding benzoic acid derivatives conjugated with glycine. Demethylenation was mainly catalyzed by CYP2D1/6 or CYP3A2/4, but also by CYP independent mechanisms. In humans, MDMA and MBDB could also be demethylenated by CYP1A2. N-demethylation was mainly catalyzed by CYP1A2, N-deethylation by CYP3A2/4. ...","MolecularFormula":"C\u003csub\u003e10\u003c/sub\u003eH\u003csub\u003e13\u003c/sub\u003eNO\u003csub\u003e2\u003c/sub\u003e","MolecularWeight":"179.22 g/mol","Non-Human Toxicity Values":"LD50 Mouse oral 13,300 ug/kg","Opticalactivity":"( + / - )","PubChemId":1614,"Record Description":["Wikipedia|PiHKAL|Phenethylamines"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"891348","RefCount":5,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/3,4-Methylenedioxyamphetamine","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q223020","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01509","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/1614","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=4764-17-4","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0041931","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/D12715","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/XJZ28FJ27W","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID40859958","Name":"3,4-Methylenedioxyamphetamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 1614, Tenamfetamine. Accessed May 7, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/1614\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/1614\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. 3,4-Methylenedioxyamphetamine. UNII: XJZ28FJ27W. Global Substance Registration System. Accessed May 7, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/XJZ28FJ27W\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/XJZ28FJ27W\u003c/a\u003e","RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed May 7, 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","Straumann I, Vizeli P, Avedisian I, Erne L, Noorshams D, Vukalovic I, Eckert A, Luethi D, Rudin D, Liechti ME. Acute effects of MDMA, MDA, lysine-MDMA, and lysine-MDA in a randomized, double-blind, placebo-controlled, crossover trial in healthy participants. Neuropsychopharmacology. January 1, 2026; 51(2):476–485."],"SMILES":"CC(CC1=CC2=C(C=C1)OCO2)N","SaltData":[{"AcidCount":1,"Amine":"3,4-Methylenedioxyamphetamine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","RName":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 122.715 34.536\"\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=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h123v35H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"M77.296 25.87V10.63M77.296 10.63 64.098 3.01M64.098 3.01 50.9 10.63\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"M50.9 10.63 37.697 3.001M48.462 12.037l-10.766-6.22\"/\u003e\u003c/g\u003e\u003cpath d=\"m37.697 3.001-13.199 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Effects":[]},"Therapeutic Uses":"Adrenergic Uptake Inhibitors; Hallucinogens; Serotonin Agents","Title":"3,4-Methylenedioxyamphetamine","UNII":"XJZ28FJ27W","Wikidata":"Q223020","Wikipedia":"3,4-Methylenedioxyamphetamine","XLogP":1.6}