# MTDA > Mediated Wiki article. Canonical URL: https://mediated.wiki/source/MTDA > Markdown URL: https://mediated.wiki/source/MTDA.md > Source: https://en.wikipedia.org/wiki/MTDA > Source revision: 1319896582 > License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/) {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = MTDA.svg | image_class = skin-invert-image | width = | caption = | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = | ATC_prefix = None | ATC_suffix = | legal_status = | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion = | CAS_number = | CAS_supplemental = | PubChem = 170864921 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = | UNII = | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = MPDA; 3-Methoxy-4,5-trimethylenedioxyamphetamine; 5-Methoxy-3,4-trimethylenedioxyamphetamine; 5-Methoxy-TDA; 5-MeO-TDA | IUPAC_name = 1-(6-methoxy-3,4-dihydro-2''H''-1,5-benzodioxepin-8-yl)propan-2-amine | C=13 | H=19 | N=1 | O=3 | SMILES = CC(CC1=CC2=C(C(=C1)OC)OCCCO2)N | StdInChI = 1S/C13H19NO3/c1-9(14)6-10-7-11(15-2)13-12(8-10)16-4-3-5-17-13/h7-9H,3-6,14H2,1-2H3 | StdInChIKey = XCXNZPQOBJFUIH-UHFFFAOYSA-N }} '''MTDA''', or '''MPDA''', also known as '''3-methoxy-4,5-trimethylenedioxyamphetamine''' or as '''5-methoxy-TDA''', is a [chemical compound](/source/chemical_compound) of the [phenethylamine](/source/substituted_phenethylamine) and [amphetamine](/source/substituted_amphetamine) families related to the [MDxx](/source/substituted_methylenedioxyphenethylamine) compounds like [MDMA](/source/MDMA) and the [EDxx](/source/substituted_ethylenedioxyphenethylamine) compounds like [EDMA](/source/EDMA_(drug)).{{CitePiHKAL}} "A couple of diversions may be mentioned here. Before the blessed inactivity of MEDA was established, the 7-membered ring counterpart, 3-methoxy-4,5-trimethylenedioxyamphetamine (MTDA) was prepared by essentially the same procedure. The above 3-methoxy-4,5-dihydroxybenzaldehyde with trimethylene bromide gave 3-methoxy-4,5-trimethylenedioxybenzaldehyde, white solids, with a malononitrile derivative with a mp of 134–135 °C; the aldehyde with nitroethane gave the nitropropene with a mp of 86–87 °C; and this with LAH gave MTDA as the hydrochloride (mp 160–161 °C) again isolated first as the picrate. It had been tasted at up to an 8 milligram dosage (no activity, but none expected) before being abandoned."{{cite book | vauthors = Shulgin A, Manning T, Daley P | title = [The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds](/source/The_Shulgin_Index%2C_Volume_One%3A_Psychedelic_Phenethylamines_and_Related_Compounds) | location = Berkeley | volume = 1 | year = 2011 | publisher = [Transform Press](/source/Transform_Press) | isbn = 978-0-9630096-3-0 }} It is the 5-[methoxy](/source/methoxy_group) [derivative](/source/chemical_derivative) of [3,4-trimethylenedioxyamphetamine](/source/3%2C4-trimethylenedioxyamphetamine) (TDA) and the [analogue](/source/structural_analog) of [MMDA](/source/MMDA_(drug)) (5-methoxy-MDA) and [MEDA](/source/MEDA_(drug)) (5-methoxy-EDA) in which the 3,4-alkylenedioxy [ring](/source/ring_(chemistry)) is a further-expanded 3,4-trimethylenedioxy ring. It was [synthesized](/source/chemical_synthesis), tested, and described by [Alexander Shulgin](/source/Alexander_Shulgin) in his 1991 book ''[PiHKAL](/source/PiHKAL)'' (''Phenethylamines I Have Known and Loved''). He tested it at doses of up to 8{{nbsp}}mg [orally](/source/oral_administration) and observed no activity. He did not expect any activity and did not test higher doses before abandoning it, due to it being "not an interesting compound".{{cite web | vauthors = [Shulgin A](/source/Alexander_Shulgin) | title = Ask Dr. Shulgin Online June 3, 2003 | date = 3 June 2003 | publisher = Center for Cognitive Liberty & Ethics | website = cognitiveliberty.org | url = https://www.cognitiveliberty.org/ccle1/shulgin/adsarchive/methylenedioxy.htm | quote = With the specific compound MDMA, I have made only one modification of the methylenedioxy ring. This was to make it into a six membered ring, a dioxane homologue, which I called EDMA for ethylenedioxymethamphetmaine. With this homologue, I went up to twice the active dosage of MDMA and experienced none of the effects that might have been expected. A completely separate ring expansion to the dioxane homologue was explored with MMDA. The 5-membered methylenedioxy ring was expanded to the six-membered dioxane (3-methoxy-4,5-ethylenedioxyamphetamine, MEDA) which was also inactive at a 200 milligram dose. The chemistry was pursued successful up to the seven member ring, the compound named MTDA for 3-methoxy-4,5- trimethylenedioxyamphetamine was also synthesized, but human trials didn't go up very far. It was not an interesting compound (see PIHKAL, page 761). }} MTDA was first described in the [scientific literature](/source/scientific_literature) by Shulgin by 1964.{{cite journal | vauthors = Shulgin AT | title = 3-Methoxy-4 5-methylenedioxy Amphetamine, a New Psychotomimetic Agent | journal = Nature | volume = 201 | issue = 4924 | pages = 1120–1121 | date = March 1964 | pmid = 14152788 | doi = 10.1038/2011120a0 | url = https://bibliography.maps.org/resources/download/8861 | url-access = subscription | bibcode = 1964Natur.201.1120S | archive-url = https://web.archive.org/web/20250712211627/https://bibliography.maps.org/resources/download/8861 | archive-date = 2025-07-12 }}{{cite journal | vauthors = Nichols DE | title = Structure-activity relationships of phenethylamine hallucinogens | journal = Journal of Pharmaceutical Sciences | volume = 70 | issue = 8 | pages = 839–849 | date = August 1981 | pmid = 7031221 | doi = 10.1002/jps.2600700802 | bibcode = 1981JPhmS..70..839N }} == See also == * [Substituted phenethylamine](/source/Substituted_phenethylamine) * [Substituted ethylenedioxyphenethylamine](/source/Substituted_ethylenedioxyphenethylamine) * [MEDA](/source/MEDA_(drug)) (5-methoxy-EDA) == References == {{Reflist}} == External links == * [https://isomerdesign.com/pihkal/explore/286 MTDA - Isomer Design] {{Phenethylamines}} Category:Carbenes Category:Methoxyphenethylamines Category:Substituted amphetamines {{Psychoactive-stub}} --- Adapted from the Wikipedia article [MTDA](https://en.wikipedia.org/wiki/MTDA) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/MTDA?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.