MTDA
| Clinical data | |
|---|---|
| Other names | MPDA; 3-Methoxy-4,5-trimethylenedioxyamphetamine; 5-Methoxy-3,4-trimethylenedioxyamphetamine; 5-Methoxy-TDA; 5-MeO-TDA |
| ATC code |
|
| Identifiers | |
| |
| PubChem CID | |
| Chemical and physical data | |
| Formula | C13H19NO3 |
| Molar mass | 237.299 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
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
- ^ a b c d e Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "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."
- ^ a b c d e Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.
- ^ a b c d e Shulgin A (3 June 2003). "Ask Dr. Shulgin Online June 3, 2003". cognitiveliberty.org. Center for Cognitive Liberty & Ethics.
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).
- ^ Shulgin AT (March 1964). "3-Methoxy-4 5-methylenedioxy Amphetamine, a New Psychotomimetic Agent". Nature. 201 (4924): 1120–1121. Bibcode:1964Natur.201.1120S. doi:10.1038/2011120a0. PMID 14152788. Archived from the original on 2025-07-12.
- ^ Nichols DE (August 1981). "Structure-activity relationships of phenethylamine hallucinogens". Journal of Pharmaceutical Sciences. 70 (8): 839–849. Bibcode:1981JPhmS..70..839N. doi:10.1002/jps.2600700802. PMID 7031221.