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

psychedelic drugs Psychedelics are a subclass of Hallucinogen, hallucinogenic drugs whose primary effect is to trigger psychoactive drug, non-ordinary mental states (known as psychedelic experiences or "trips") and a perceived "expansion of consciousness". Also ...

similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA,

2,4-DMA 2,4-Dimethoxyamphetamine (2,4-DMA), also known as DMA-3, is a drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. It was reported by Alexander Shulgin to be active at a d ...

2,5-DMA 2,5-Dimethoxyamphetamine (2,5-DMA), also known as DMA-4 or as DOH, is a drug of the substituted phenethylamine, phenethylamine and substituted amphetamine, amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional iso ...

, 2,6-DMA,

3,4-DMA 3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers. The drug has been assessed ...

, 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 biochemist, broad researcher of synthetic psychoactive compounds, and author of works regarding these, who independently explored the organic chemistry and ph ...

in his book ''

PiHKAL ''PiHKAL: A Chemical Love Story'' is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is Psychoactive drug, psychoactive phenethylamine Derivative (chemistry), chemical derivatives, notably those that act ...

''. Little is known about their dangers or toxicity.

Pharmacology

, and their ''N''-methyl analogues all fail to produce stimulus generalization to

dextroamphetamine Dextroamphetamine (international nonproprietary name, INN: dexamfetamine) is a potent central nervous system (CNS) stimulant and enantiomer of amphetamine that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narc ...

in rodent drug discrimination tests, suggesting that they lack

psychostimulant Stimulants (also known as central nervous system stimulants, or psychostimulants, or colloquially as uppers) are a class of drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition ...

- or amphetamine-like effects, at least in rodents. This is in contrast to 2-methoxyamphetamine (OMA), 3-methoxyamphetamine (MMA), and 4-methoxyamphetamine (PMA), which all produce substitution for dextroampehtamine, albeit with far lower

potency Potency may refer to: * Potency (pharmacology), a measure of the activity of a drug in a biological system * Virility * Cell potency, a measure of the differentiation potential of stem cells * In homeopathic dilutions, potency is a measure of ho ...

than amphetamine,

methamphetamine Methamphetamine (contracted from ) is a potent central nervous system (CNS) stimulant that is mainly used as a recreational drug use, recreational or Performance-enhancing substance, performance-enhancing drug and less commonly as a secon ...

, and other stimulants.

Positional isomers

2,4-DMA

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

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 (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

homologue of

2C-H 2C-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA), is a lesser-known drug of the phenethylamine and 2C (4-substituted 2,5-dimethoxyphenethylamine) families. It is the parent compound of the 2C drugs. Use and effects There is no re ...

and could be called "DOH" under the DO naming scheme. It is the parent compound of the DOx series of drugs. * ''Dosage'': 80–160 mg * ''Duration'': 6–8 hours * ''Effects'':

Mydriasis Mydriasis is the Pupillary dilation, dilation of the pupil, usually having a non-physiological cause, or sometimes a physiological pupillary response. Non-physiological causes of mydriasis include disease, Physical trauma, trauma, or the use of c ...

, increase in heart rate, no psychedelic effects * ''History'': 2,5-DMA was first synthesized in Tuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939. It is a low-potency

serotonin Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...

5-HT_2A receptor

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given Receptor (biochemistry), receptor, but have only partial Intrinsic activity, efficacy at the receptor relative to a full agonist. They may also be considered Ligand (bio ...

and has also been assessed at several other

target Target may refer to: Warfare and shooting * Shooting target, used in marksmanship training and various shooting sports ** Bullseye (target), the goal one for which one aims in many of these sports ** Aiming point, in field artille ...

s. The drug does not appear to bind to the

monoamine transporter Monoamine transporters (MATs) are proteins that function as integral Cell membrane, plasma-membrane Neurotransmitter transporter, transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are se ...

3,4-DMA

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

Mescaline Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a natural product, naturally occurring psychedelic drug, psychedelic alkaloid, protoalkaloid of the substituted phenethylamine class, found ...

-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 ...

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

U.S. Army The United States Army (USA) is the primary land service branch of the United States Department of Defense. It is designated as the Army of the United States in the United States Constitution.Article II, section 2, clause 1 of the United Stat ...

's chemical warfare group while researching many potentially weaponizable

drugs A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via inhalation, injection, smoking, ingestio ...

probably as part of the

Edgewood Arsenal experiments From 1948 to 1975, the U.S. Army Chemical Corps conducted classified information, classified human subject research at the Edgewood Arsenal facility in Maryland.''Possible Long-Term Health Effects of Short-Term Exposure to Chemical Agents'', Comm ...

. The

Edgewood Arsenal Aberdeen Proving Ground (APG) 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 APG. There are 11 major commands among the tenant units, ...

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.

3,5-DMA

Not known to have been assessed in humans and inactive in terms of psychedelic-like effects in rodents.

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 Sing ...

at the federal level in the

United States The United States of America (USA), also known as the United States (U.S.) or America, is a country primarily located in North America. It is a federal republic of 50 U.S. state, states and a federal capital district, Washington, D.C. The 48 ...

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
{{Chemical classes of psychoactive drugs Methoxyphenethylamines Phenol ethers Substituted amphetamines