Dimethoxyamphetamine

3,4-Dimethoxyamphetamine
	<img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/14/3%2C4-dma.png/220px-3%2C4-dma.png" decoding="async" width="220" height="106" class="mw-file-element" data-file-width="708" data-file-height="341">
Names
	IUPAC name 1-(3,4-dimethoxyphenyl)propan-2-amine
Identifiers
CAS Number	120-26-3;
Abbreviations	3,4-DMA
ChEMBL	ChEMBL277540;
ChemSpider	8116;
EC Number	204-383-7;
PubChem CID	8423;
UNII	EMH5PUB78V;
	InChI 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
Chemical formula	C11H17NO2
Molar mass	195.262 g·mol−1
Pharmacology
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); NZ: Class A; US: Schedule I;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,5-Dimethoxyamphetamine
	<img src="//upload.wikimedia.org/wikipedia/commons/thumb/2/27/2%2C5-DMA.svg/220px-2%2C5-DMA.svg.png" decoding="async" width="220" height="209" class="mw-file-element" data-file-width="400" data-file-height="380">
Names
	IUPAC name 1-(2,5-dimethoxyphenyl)propan-2-amine
Identifiers
CAS Number	2801-68-5;
Abbreviations	2,5-DMA
ChEMBL	ChEMBL8642;
ChemSpider	56526;
EC Number	220-540-2;
PubChem CID	62787;
UNII	OIM1536TQQ;
	InChI 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
Chemical formula	C11H17NO2
Molar mass	195.262 g·mol−1
Pharmacology
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); NZ: Class A; US: Schedule I;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

2,4-Dimethoxyamphetamine
	<img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/2%2C4-DMA.png/220px-2%2C4-DMA.png" decoding="async" width="220" height="155" class="mw-file-element" data-file-width="651" data-file-height="458">
Names
	IUPAC name 1-(2,4-dimethoxyphenyl)propan-2-amine
Identifiers
CAS Number	23690-13-3 <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" data-file-width="600" data-file-height="600"> ;
Abbreviations	2,4-DMA
ChEMBL	ChEMBL282734;
ChemSpider	124411;
PubChem CID	141047;
UNII	GT33R7Q58G <img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" data-file-width="600" data-file-height="600"> ;
	InChI 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
Chemical formula	C11H17NO2
Molar mass	195.262 g·mol−1
Pharmacology
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); NZ: Class A; US: Schedule I;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

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

2,5-DMA

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

Dosage: 80–160 mg^[2]
Duration: 6–8 hours
Effects: Mydriasis, increase in heart rate
History: 2,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.^[3]

3,4-DMA

Dosage: 160 milligrams orally^[1]
Duration: unknown
Effects: Mescaline-like visuals
History: Experiments on psychiatric patients who were given 3,4-DMA at dosages of 70 mg to 700 mg by IV injection took place at the New York State Psychiatric Institute and other places in the early 1960s and were carried out by the U.S. Army's chemical warfare group while researching many potentially weaponizable drugs probably as part of the Edgewood Arsenal experiments. The Edgewood Arsenal code name for 3,4-DMA was EA-1316.^[1]

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

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]

References

^ ^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.
^ "PiHKAL". isomerdesign.com. Retrieved 2012-03-17.
^ Baltzly, Richard; Buck, Johannes S. (1940). "Amines Related to 2,5-Dimethoxyphenethylamine". Journal of the Chemical Society. 62: 161–164. doi:10.1021/ja01858a046.
^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-21.
^ ^a ^b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534
^ "Misuse of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18.

External links

[Cite-1] 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.

[PART_1308_—_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-4] "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-21.

[Poisons_Standard-5] Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534

[6] "Misuse of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18.

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