Dimethoxyamphetamine (DMA) is a series of six lesser-known

psychedelic drugs Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of ...

similar in structure to the three isomers of

methoxyamphetamine Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with ...

and six isomers of

trimethoxyamphetamine Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs ...

. 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 Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

in his book '' PiHKAL''. 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 In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

homologue of 2C-H and could be called "DOH" under the DO naming scheme. * ''Dosage'': 80–160 mg * ''Duration'': 6–8 hours * ''Effects'':

Mydriasis Mydriasis is the dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, trauma, or the use of certain types of drugs. Normally, as ...

, increase in heart rate * ''History'': 2,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.

3,4-DMA

* ''Dosage'': 160 milligrams orally * ''Duration'': unknown * ''Effects'':

Mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological sou ...

-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 The New York State Psychiatric Institute, located at the Columbia University Irving Medical Center in the Washington Heights neighborhood of Manhattan, New York City, was established in 1895 as one of the first institutions in the United States t ...

and other places in the early 1960s and were carried out by the

U.S. Army The United States Army (USA) is the land service branch of the United States Armed Forces. It is one of the eight U.S. uniformed services, and is designated as the Army of the United States in the U.S. Constitution.Article II, section 2, cl ...

's chemical warfare group while researching many potentially weaponizable

drugs A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhalat ...

probably as part of the

Edgewood Arsenal experiments From 1948 to 1975, the U.S. Army Chemical Corps conducted classified human subject research at the Edgewood Arsenal facility in Maryland. The purpose was to evaluate the impact of low-dose chemical warfare agents on military personnel and to tes ...

. The

Edgewood Arsenal Aberdeen Proving Ground (APG) (sometimes erroneously called Aberdeen Proving ''Grounds'') is a U.S. Army facility located adjacent to Aberdeen, Harford County, Maryland, United States. More than 7,500 civilians and 5,000 military personnel work at ...

code name for 3,4-DMA was EA-1316. 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 A controlled substance is generally a drug or chemical whose manufacture, possession and use is regulated by a government, such as illicitly used drugs or prescription medications that are designated by law. Some treaties, notably the Single C ...

at the federal level in the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...

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.

Australia

DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 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.

New Zealand

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

References

External links

2,4-DMA Entry in ''PiHKAL''

2,4-DMA Entry in PiHKAL • info

2,5-DMA Entry in ''PiHKAL''

2,5-DMA Entry in PiHKAL • info

3,4-DMA Entry in ''PiHKAL''

3,4-DMA Entry in PiHKAL • info
{{Monoamine releasing agents Substituted amphetamines Phenol ethers