{{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = 2T-MMDA-3a.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="Trachsel_2013" /><ref name="Shulgin_2011" /><ref name="PiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = Unknown<ref name="PiHKAL" /> | elimination_half-life = | duration_of_action = Unknown<ref name="PiHKAL" /><ref name="Trachsel_2013" /><ref name="Shulgin_2011" /> | excretion =
<!-- Identifiers --> | CAS_number = 952017-31-1 | CAS_supplemental = | PubChem = 44719661 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 23553177 | UNII = 5GP2MP7YKC | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = 2-MeS-MDA; 2-Methylthio-3,4-methylenedioxyamphetamine; 3,4-Methylenedioxy-2-methylthioamphetamine
<!-- Chemical data --> | IUPAC_name = 1-(4-methylsulfanyl-1,3-benzodioxol-5-yl)propan-2-amine | C=11 | H=15 | N=1 | O=2 | S=1 | SMILES = CC(CC1=C(C2=C(C=C1)OCO2)SC)N | StdInChI = 1S/C11H15NO2S/c1-7(12)5-8-3-4-9-10(11(8)15-2)14-6-13-9/h3-4,7H,5-6,12H2,1-2H3 | StdInChIKey = NMNCXGKWTVPITN-UHFFFAOYSA-N }}
'''2T-MMDA-3a''', also known as '''2-methylthio-3,4-methylenedioxyamphetamine''' ('''2-MeS-MDA'''), is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to 3,4-methylenedioxyamphetamine (MDA).<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="PiHKAL">{{CitePiHKAL}} {{cite web | title = 2T-MMDA-3a | url = https://erowid.org/library/books_online/pihkal/pihkal166.shtml }}</ref> It is the derivative of MDA with a 2-methylthio substitution and is the analogue of MMDA-3a with a 2-methylthio group instead of a 2-methoxy group.<ref name="Trachsel_2013" /><ref name="PiHKAL" />
2T-MMDA-3a was included as an entry in Alexander Shulgin's book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="Trachsel_2013" /><ref name="PiHKAL" /> Its dose was listed as greater than 12{{nbsp}}mg orally, its duration was listed as unknown, and its effects were not described.<ref name="Trachsel_2013" /><ref name="Shulgin_2011" /><ref name="PiHKAL" /> However, in Shulgin's 2011 book ''The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds'', he stated that a 12{{nbsp}}mg dose produced threshold effects, but he did not assess higher doses.<ref name="Trachsel_2013" /><ref name="Shulgin_2011">{{cite book | vauthors = Shulgin A, Manning T, Daley P | title = The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds | location = Berkeley | volume = 1 | year = 2011 | publisher = Transform Press | isbn = 978-0-9630096-3-0 | quote = 2T-MMDA-3a [...] (6,7) [...] (6) Synthesis (Shulgin and Shulgin, 1991). (7) Threshold oral activity in humans at 12 mg; duration unknown (Shulgin and Shulgin, 1991). }}</ref><ref name="PiHKAL" /> In addition, Daniel Trachsel has classified 2T-MMDA-3a as a hallucinogen.<ref name="Trachsel_2013" />
The chemical synthesis of 2T-MMDA-3a was described by Shulgin in ''PiHKAL''.<ref name="PiHKAL" /> Numerous other sulfur-containing phenethylamine analogues are also possible.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Trachsel_2013" />
2T-MMDA-3a was first described in the scientific literature by Shulgin in ''PiHKAL'' in 1991.<ref name="Shulgin_2011" /><ref name="PiHKAL" /> It is a controlled substance in Canada under phenethylamine blanket-ban language.<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>
== See also == * Substituted methylenedioxyphenethylamine * 4T-MMDA-2
== References == {{Reflist}}
== External links == * [https://isomerdesign.com/pihkal/explore/166 2T-MMDA-3a - Isomer Design] * [https://erowid.org/library/books_online/pihkal/pihkal166.shtml 2T-MMDA-3a - PiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/pk/166 2T-MMDA-3a - PiHKAL - Isomer Design]
{{Psychedelics}} {{Phenethylamines}}
Category:Methylenedioxyamphetamines Category:Methylthio compounds Category:PiHKAL Category:Psychedelic phenethylamines