:Dimethoxyamphetamine

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.{{CitePiHKAL}} Little is known about their dangers or toxicity.

Pharmacology

3,4-DMA, 2,4-DMA, 2,5-DMA, and their N-methyl analogues all fail to produce stimulus generalization to dextroamphetamine in rodent drug discrimination tests, suggesting that they lack psychostimulant- or amphetamine-like effects, at least in rodents.{{cite journal | vauthors = Glennon RA | title = Stimulus properties of hallucinogenic phenalkylamines and related designer drugs: formulation of structure-activity relationships | journal = NIDA Res Monogr | volume = 94 | issue = | pages = 43–67 | date = 1989 | pmid = 2575229 | doi = | url = https://archives.nida.nih.gov/sites/default/files/monograph94.pdf#page=54}} 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 than amphetamine, methamphetamine, and other stimulants.

Positional isomers

=2,4-DMA=

File:2,4-DMA.svg]]

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

=2,5-DMA=

File:2,5-DMA.svg]]

2,5-DMA is the alpha-methyl homologue of 2C-H 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{{Cite web |title=PiHKAL | url = http://isomerdesign.com/PiHKAL/read.php?domain=pk&id=54 |agency=isomerdesign.com | access-date = 2012-03-17 }}
Duration: 6–8 hours
Effects: Mydriasis, 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.{{cite journal|last1=Baltzly|first1=Richard|last2=Buck|first2=Johannes S.|title=Amines Related to 2,5-Dimethoxyphenethylamine |journal=Journal of the Chemical Society|date=1940|volume=62|pages=161–164 | doi = 10.1021/ja01858a046 }}

It is a low-potency serotonin 5-HT_2A receptor partial agonist and has also been assessed at several other targets.{{cite journal | last1=Luethi | first1=Dino | last2=Rudin | first2=Deborah | last3=Hoener | first3=Marius C. | last4=Liechti | first4=Matthias E. | title=Monoamine Receptor and Transporter Interaction Profiles of 4-Alkyl-Substituted 2,5-Dimethoxyamphetamines | journal=The FASEB Journal | volume=36 | issue=S1 | date=2022 | issn=0892-6638 | doi=10.1096/fasebj.2022.36.S1.R2691 | page= | doi-access=free | url=https://www.researchgate.net/profile/Dino-Luethi/publication/360369275_Monoamine_Receptor_and_Transporter_Interaction_Profiles_of_4-Alkyl-Substituted_25-Dimethoxyamphetamines/links/627531dc107cae29198ee5f2/Monoamine-Receptor-and-Transporter-Interaction-Profiles-of-4-Alkyl-Substituted-2-5-Dimethoxyamphetamines.pdf }} The drug does not appear to bind to the monoamine transporters.

=3,4-DMA=

File:3,4-Dimethoxyamphetamine.svg]]

Dosage: 160 milligrams orally
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.

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 at the federal level in the United States and is therefore illegal to buy, possess, and sell.{{Cite web |url=http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |title=§1308.11 Schedule I. |access-date=2014-12-21 |archive-date=2009-08-27 |archive-url=https://web.archive.org/web/20090827043725/http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm |url-status=dead }} 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.{{Cite web |title=Misuse of Drugs Act 1975| url = http://www.legislation.govt.nz/act/public/1975/0116/latest/whole.html?search=qs_act%40bill%40regulation%40deemedreg_methamphetamine_resel_25_h&p=1#DLM436106 |agency=New Zealand Government | access-date = 2016-01-18 }}

References

External links

[http://www.erowid.org/library/books_online/pihkal/pihkal053.shtml 2,4-DMA Entry in PiHKAL]
[http://pihkal.info/read.php?domain=pk&id=53 2,4-DMA Entry in PiHKAL • info]
[http://www.erowid.org/library/books_online/pihkal/pihkal054.shtml 2,5-DMA Entry in PiHKAL]
[http://pihkal.info/read.php?domain=pk&id=54 2,5-DMA Entry in PiHKAL • info]
[http://www.erowid.org/library/books_online/pihkal/pihkal055.shtml 3,4-DMA Entry in PiHKAL]
[http://pihkal.info/read.php?domain=pk&id=55 3,4-DMA Entry in PiHKAL • info]