2,5-DMA

Dimethoxyamphetamine

Names
IUPAC name 2-(3,4-Dimethoxyphenyl)propylamine
Identifiers
3D model (JSmol)	Interactive image Interactive image
ChemSpider	82404 Y
PubChem CID	91255
InChI InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3 Y Key: DHLWJXGSZDJWKK-UHFFFAOYSA-N Y InChI=1/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3 Key: DHLWJXGSZDJWKK-UHFFFAOYAZ
SMILES C1(=CC(=CC=C1CC(C)N)OC)OC O(c1c(cccc1OC)CC(N)C)C
Properties
Chemical formula	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).
Y  (what is YN ?)
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 characterized by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known And Loved). Little is known about their dangers or toxicity.

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

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.

3,4-DMA has known use as a precursor in the synthesis of dimoxyline.

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. 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.

DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). 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.

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