Dimethoxyamphetamine

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Dimethoxyamphetamine
2,4-DMA.png
DMA-3d-sticks.png
Identifiers
PubChem 91255
ChemSpider 82404 YesY
ChEMBL CHEMBL280855 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C11H17NO2
Molar mass 195.26 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

DMA, or dimethoxyamphetamine, is a series of lesser-known psychedelic drugs similar in structure to amphetamine and to trimethoxyamphetamine (TMA). They were first collectively charictarized by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known And Loved).[1] Little is known about their dangers or toxicity.

Positional isomers[edit]

2,4-DMA[edit]

2,4-DMA, or 2,4-dimethoxy-amphetamine


  • Dosage: 60 mg or greater
  • Duration: "Probably short."
  • Effects: stimulative, amphetamine-like effects

2,5-DMA[edit]

2,5-DMA, or 2,5-dimethoxy-amphetamine


2,5-DMA is the alpha-methyl homologue of 2C-H and could be called "DOH" under the DO naming scheme.

3,4-DMA[edit]

3,4-DMA, or 3,4-dimethoxy-amphetamine


Note that two other positional isomers of dimethoxyamphetamine, 2,6-DMA and 3,5-DMA, have also been made, but these drugs have not been tested in humans and their effects are unknown. However, it is likely that these compounds would also produce amphetamine-like stimulation or possibly hallucinogenic effects.

Legal Status[edit]

United States[edit]

2,5-dimethoxyamphetamine is listed as a Scheduled I controlled substance at the federal level in the United States and is therefore illegal to buy, posses, and sell.[4] 2,4-dimethoxyamphetamine, 2,6-dimethoxyamphetamine, 3,4-dimethoxyamphetamine, and 3,5-dimethoxyamphetamine are each position isomers of 2,5-dimethoxyamphetamine, they are therefore all Schedule I controlled substances as well.

See also[edit]

References[edit]

  1. ^ a b c Shulgin, Alexander; Ann Shulgin (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. 
  2. ^ "PiHKAL". isomerdesign.com. Retrieved 2012-03-17. 
  3. ^ Baltzly, Richard; Buck, Johannes S. (1940). "Amines Related to 2,5-Dimethoxyphenethylamine.". Journal of Chemical Society 62: 161–164. 
  4. ^ §1308.11 Schedule I.

External links[edit]