MTDA

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MTDA
MTDA.svg
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
Formula C13H19NO3
Molar mass 237.299 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. [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]

Contents

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.
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