{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = MADAM-6.svg | image_class = skin-invert-image | width = 235px | caption =

<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="PiHKAL" /> | class = | ATC_prefix = None | ATC_suffix =

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<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /> | excretion =

<!-- Identifiers --> | CAS_number = 207740-46-3 | CAS_supplemental = | PubChem = 44719578 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 21106340 | UNII = W3H6GHJ73C | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 6-Methyl-MDMA; 2,''N''-Dimethyl-4,5-methylenedioxyamphetamine

<!-- Chemical data --> | IUPAC_name = ''N''-methyl-1-(6-methyl-2''H''-1,3-benzodioxol-5-yl)propan-2-amine | C=12 | H=17 | N=1 | O=2 | SMILES = C1(=CC2=C(C=C1CC(C)NC)OCO2)C | StdInChI = 1S/C12H17NO2/c1-8-4-11-12(15-7-14-11)6-10(8)5-9(2)13-3/h4,6,9,13H,5,7H2,1-3H3 | StdInChIKey = CRQPDNIUPWXPNK-UHFFFAOYSA-N }}

'''MADAM-6''', also known as '''2,''N''-dimethyl-4,5-methylenedioxyamphetamine''' or as '''6-methyl-MDMA''', is a drug of the phenethylamine, amphetamine, and MDxx families related to MDMA.<ref name="PiHKAL">{{CitePiHKAL}} [http://www.erowid.org/library/books_online/pihkal/pihkal098.shtml MADAM-6 entry]</ref><ref>{{Cite journal | vauthors = Patt M, Gündisch D, Wüllner U, Blocher A, Kovar KA, Machulla HJ | title = N-&#91;11C&#93;methyl-3,4-methylenedioxyamphetamine (Ecstasy) and 2-methyl-N-&#91;11C&#93;methyl-4,5-methylenedioxyamphetamine: Synthesis and biodistribution studies | journal = Journal of Radioanalytical and Nuclear Chemistry | volume = 240 | issue = 2 | pages = 535–540 | year = 1999 | doi = 10.1007/BF02349410 | s2cid = 96272983 }}</ref>

==Use and effects== In his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved''), Alexander Shulgin lists MADAM-6's dose as greater than 280{{nbsp}}mg orally and its duration as unknown.<ref name="PiHKAL" /> MADAM-6 produced few to no effects at tested doses and Shulgin described it as "not active".<ref name="PiHKAL" />

==History== MADAM-6 was first described in the literature by Alexander Shulgin in his book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'') in 1991.<ref name="PiHKAL" />

==Research== MADAM-6 has been studied for its potential antiparkinsonian effects.<ref name="US2015025063">{{cite patent | title = Antiparkinsonian Action Of Phenylisopropylamines | number = 2015025063 | country = US | status = patent | pubdate = 2014-09-30 | gdate = 2015-01-22 | inventor = Caron MG, Sotnikova TD, Gainetdinov RR | assign1 = Duke University | url = https://pubchem.ncbi.nlm.nih.gov/patent/US2015025063 }}</ref> However, no clinical trials suggest the drug is effective against Parkinson's disease.

==See also== * Substituted methylenedioxyphenethylamine

==References== {{Reflist}}

==External links== * [https://isomerdesign.com/pihkal/explore/98 MADAM-6 - Isomer Design] * [https://www.erowid.org/library/books_online/pihkal/pihkal098.shtml MADAM-6 - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/98 MADAM-6 - PiHKAL - Isomer Design]

{{Phenethylamines}}

Category:Methamphetamines Category:Methylenedioxyamphetamines Category:PiHKAL