MTDA

MTDA
Clinical data
Other namesMPDA; 3-Methoxy-4,5-trimethylenedioxyamphetamine; 5-Methoxy-3,4-trimethylenedioxyamphetamine; 5-Methoxy-TDA; 5-MeO-TDA
ATC code
  • None
Identifiers
  • 1-(6-methoxy-3,4-dihydro-2H-1,5-benzodioxepin-8-yl)propan-2-amine
PubChem CID
Chemical and physical data
FormulaC13H19NO3
Molar mass237.299 g·mol−1
3D model (JSmol)
  • CC(CC1=CC2=C(C(=C1)OC)OCCCO2)N
  • InChI=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
  • Key: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. 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. It was synthesized, tested, and described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). He tested it at doses of up to 8 mg orally 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". MTDA was first described in the scientific literature by Shulgin by 1964.

See also

References

  1. 1 2 3 4 5 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."
  2. 1 2 3 4 5 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.
  3. 1 2 3 4 5 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).
  4. ↑ 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.
  5. ↑ 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.