Dimethoxyamphetamine

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Dimethoxyamphetamine
2,4-DMA.png
DMA-3d-sticks.png
Names
IUPAC name
2-(3,4-Dimethoxyphenyl)propylamine
Identifiers
ChEMBL ChEMBL280855 YesY
ChemSpider 82404 YesY
Jmol interactive 3D Image
Image
PubChem 91255
Properties
C11H17NO2
Molar mass 195.26 g/mol
Except where otherwise noted, 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, possess, 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.

Australia[edit]

DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[5] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[5]

Australia[edit]

DMA is considered a Class A controlled drug under the Misuse of Drugs Act 1975[6]

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.
  5. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  6. ^ "Misue of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18. 

External links[edit]