MTDA

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

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<!-- Identifiers --> | 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

<!-- Chemical data --> | 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 of the phenethylamine and amphetamine families related to the MDxx compounds like MDMA and the EDxx compounds like EDMA.<ref name="PiHKAL">{{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."</ref><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 }}</ref><ref name="Shulgin_2003" /> It is the 5-methoxy derivative of 3,4-trimethylenedioxyamphetamine (TDA) and the analogue of MMDA (5-methoxy-MDA) and MEDA (5-methoxy-EDA) in which the 3,4-alkylenedioxy ring is a further-expanded 3,4-trimethylenedioxy ring.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Shulgin_2003" /> It was synthesized, tested, and described by Alexander Shulgin in his 1991 book ''PiHKAL'' (''Phenethylamines I Have Known and Loved'').<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Shulgin_2003" /> He tested it at doses of up to 8{{nbsp}}mg orally and observed no activity.<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Shulgin_2003" /> He did not expect any activity and did not test higher doses before abandoning it, due to it being "not an interesting compound".<ref name="PiHKAL" /><ref name="Shulgin_2011" /><ref name="Shulgin_2003">{{cite web | vauthors = Shulgin A | 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). }}</ref> MTDA was first described in the scientific literature by Shulgin by 1964.<ref name="Shulgin_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 }}</ref><ref name="Nichols_1981">{{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 }}</ref>

== See also == * Substituted phenethylamine * Substituted ethylenedioxyphenethylamine * MEDA (5-methoxy-EDA)

== References == {{Reflist}}

== External links == * [https://isomerdesign.com/pihkal/explore/286 MTDA - Isomer Design]

{{Phenethylamines}}

Category:Carbenes Category:Methoxyphenethylamines Category:Substituted amphetamines

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