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Dimethoxyamphetamine (DMA) is a series of six lesser-knownpsychedelic drugs similar in structure to the three isomers ofmethoxyamphetamine and six isomers oftrimethoxyamphetamine. The isomers are 2,3-DMA,2,4-DMA,2,5-DMA, 2,6-DMA,3,4-DMA, and3,5-DMA. Three of the isomers were characterized byAlexander Shulgin in his bookPiHKAL.^[1] Little is known about their dangers or toxicity.

3,4-DMA,2,4-DMA,2,5-DMA, and theirN-methylanalogues all fail to produce stimulus generalization todextroamphetamine in rodentdrug discrimination tests, suggesting that they lackpsychostimulant- or amphetamine-like effects, at least in rodents.^[2] This is in contrast to2-methoxyamphetamine (OMA),3-methoxyamphetamine (MMA), and4-methoxyamphetamine (PMA), which all produce substitution for dextroampehtamine, albeit with far lowerpotency than amphetamine,methamphetamine, and other stimulants.^[2]

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

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

2,5-DMA is the alpha-methylhomologue of2C-H and could be called "DOH" under the DO naming scheme. It is theparent compound of theDOx series of drugs.

• Dosage: 80–160 mg^[3]
• Duration: 6–8 hours
• Effects:Mydriasis,increase in heart rate, no psychedelic effects
• History: 2,5-DMA was firstsynthesized inTuckahoe, New York by Richard Baltzly and Johannes S. Buck in 1939.^[4]

It is a low-potencyserotonin5-HT_2A receptorpartial agonist and has also been assessed at several othertargets.^[5] The drug does not appear to bind to themonoamine transporters.^[5]

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

• 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 byIV injection took place at theNew York State Psychiatric Institute and other places in the early 1960s and were carried out by theU.S. Army's chemical warfare group while researching many potentially weaponizabledrugs probably as part of theEdgewood Arsenal experiments. TheEdgewood 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.

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

DMA is considered a Schedule 9 prohibited substance in Australia under thePoisons Standard (October 2015).^[6] 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.^[6]

DMA is considered a Class A controlled drug under the Misuse of Drugs Act 1975.^[7]

2,5-Dimethoxyamphetamine is listed as a Scheduled Icontrolled substance at the federal level in theUnited States and is therefore illegal to buy, possess, and sell.^[8] 2,4-dimethoxyamphetamine, 2,6-dimethoxyamphetamine, 3,4-dimethoxyamphetamine, and 3,5-dimethoxyamphetamine are eachposition isomers of 2,5-dimethoxyamphetamine, they are therefore all Schedule I controlled substances as well.

• Substituted methoxyphenethylamine
• Methoxyamphetamine
• Trimethoxyamphetamine (TMA)
• Methoxyphenethylamine
• Dimethoxyphenethylamine
• Trimethoxyphenethylamine

• 2,4-DMA Entry inPiHKAL
• 2,4-DMA Entry in PiHKAL • info
• 2,5-DMA Entry inPiHKAL
• 2,5-DMA Entry in PiHKAL • info
• 3,4-DMA Entry inPiHKAL
• 3,4-DMA Entry in PiHKAL • info

• Methoxyphenethylamines
• Phenol ethers
• Substituted amphetamines

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