Chemistry:MTDA
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.[1][2][3] 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.[1][2][3] It was synthesized, tested, and described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[1][2][3] He tested it at doses of up to 8 mg orally and observed no activity.[1][2][3] He did not expect any activity and did not test higher doses before abandoning it, due to it being "not an interesting compound".[1][2][3] MTDA was first described in the scientific literature by Shulgin by 1964.[4][5]
See also
- Substituted phenethylamine
- Substituted ethylenedioxyphenethylamine
- MEDA (5-methoxy-EDA)
References
- ↑ 1.0 1.1 1.2 1.3 1.4 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml. "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."
- ↑ 2.0 2.1 2.2 2.3 2.4 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0.
- ↑ 3.0 3.1 3.2 3.3 3.4 "Ask Dr. Shulgin Online June 3, 2003". Center for Cognitive Liberty & Ethics. 3 June 2003. https://www.cognitiveliberty.org/ccle1/shulgin/adsarchive/methylenedioxy.htm. "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)."
- ↑ "3-Methoxy-4 5-methylenedioxy Amphetamine, a New Psychotomimetic Agent". Nature 201 (4924): 1120–1121. March 1964. doi:10.1038/2011120a0. PMID 14152788. Bibcode: 1964Natur.201.1120S. https://bibliography.maps.org/resources/download/8861.
- ↑ "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences 70 (8): 839–849. August 1981. doi:10.1002/jps.2600700802. PMID 7031221. Bibcode: 1981JPhmS..70..839N.
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