Dimethoxyamphetamine

Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and 3,5-DMA. Three of the isomers were characterized by Alexander Shulgin in his book PiHKAL.[1] Little is known about their dangers or toxicity.

Positional isomers

2,4-DMA

2,4-Dimethoxyamphetamine
Names
IUPAC name
1-(2,4-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations 2,4-DMA
ChEMBL
ChemSpider
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)7-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: DQWOZMUBHQPFFF-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
  • Dosage: 60 mg or greater
  • Duration: "Probably short."
  • Effects: stimulative, amphetamine-like effects

2,5-DMA

2,5-Dimethoxyamphetamine
Names
IUPAC name
1-(2,5-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations 2,5-DMA
ChEMBL
ChemSpider
EC Number
  • 220-540-2
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-7-10(13-2)4-5-11(9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: LATVFYDIBMDBSY-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

3,4-DMA

3,4-Dimethoxyamphetamine
Names
IUPAC name
1-(3,4-dimethoxyphenyl)propan-2-amine
Identifiers
Abbreviations 3,4-DMA
ChEMBL
ChemSpider
EC Number
  • 204-383-7
UNII
  • InChI=1S/C11H17NO2/c1-8(12)6-9-4-5-10(13-2)11(7-9)14-3/h4-5,7-8H,6,12H2,1-3H3
    Key: KAZPHAGSWZTKDW-UHFFFAOYSA-N
Properties
C11H17NO2
Molar mass 195.262 g·mol−1
Pharmacology
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

United States

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

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]

New Zealand

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

See also

References

  1. ^ a b c Shulgin, Alexander; Shulgin, Ann (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 the Chemical Society. 62: 161–164. doi:10.1021/ja01858a046.
  4. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-21.
  5. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
  6. ^ "Misuse of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18.