This article needs more reliable medical references for verification or relies too heavily on primary sources. Please review the contents of the article and add the appropriate references if you can. Unsourced or poorly sourced material may be challenged and removed. Find sources: "Dimethoxyamphetamine" – news · newspapers · books · scholar · JSTOR(December 2014)
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.[1] Little is known about their dangers or toxicity.
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.[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.
Legal statusEdit
United StatesEdit
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.[4] 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.
AustraliaEdit
DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).[5] 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.[5]
New ZealandEdit
DMA is considered a Class A controlled drug under the Misuse of Drugs Act 1975.[6]
^Baltzly, Richard; Buck, Johannes S. (1940). "Amines Related to 2,5-Dimethoxyphenethylamine". Journal of the Chemical Society. 62: 161–164. doi:10.1021/ja01858a046.
^ Archived from the original on 2009-08-27. Retrieved 2014-12-21.
^"Misuse of Drugs Act 1975". New Zealand Government. Retrieved 2016-01-18.
External linksEdit
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
August 28, 2023
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This article needs more reliable medical references for verification or relies too heavily on primary sources Please review the contents of the article and add the appropriate references if you can Unsourced or poorly sourced material may be challenged and removed Find sources Dimethoxyamphetamine news newspapers books scholar JSTOR December 2014 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 1 Little is known about their dangers or toxicity Contents 1 Positional isomers 1 1 2 4 DMA 1 2 2 5 DMA 1 3 3 4 DMA 2 Legal status 2 1 United States 2 2 Australia 2 3 New Zealand 3 See also 4 References 5 External linksPositional isomers Edit2 4 DMA Edit 2 4 Dimethoxyamphetamine NamesIUPAC name 1 2 4 dimethoxyphenyl propan 2 amineIdentifiersCAS Number 23690 13 3 YAbbreviations 2 4 DMAChEMBL ChEMBL282734ChemSpider 124411PubChem CID 141047UNII GT33R7Q58G YInChI InChI 1S C11H17NO2 c1 8 12 6 9 4 5 10 13 2 7 11 9 14 3 h4 5 7 8H 6 12H2 1 3H3Key DQWOZMUBHQPFFF UHFFFAOYSA NPropertiesChemical formula C 11H 17N O 2Molar mass 195 262 g mol 1PharmacologyLegal status AU S9 Prohibited substance BR Class F2 Prohibited psychotropics NZ Class A US Schedule IExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Dosage 60 mg or greater Duration Probably short Effects stimulative amphetamine like effects 2 5 DMA Edit 2 5 Dimethoxyamphetamine NamesIUPAC name 1 2 5 dimethoxyphenyl propan 2 amineIdentifiersCAS Number 2801 68 5Abbreviations 2 5 DMAChEMBL ChEMBL8642ChemSpider 56526EC Number 220 540 2PubChem CID 62787UNII OIM1536TQQInChI InChI 1S C11H17NO2 c1 8 12 6 9 7 10 13 2 4 5 11 9 14 3 h4 5 7 8H 6 12H2 1 3H3Key LATVFYDIBMDBSY UHFFFAOYSA NPropertiesChemical formula C 11H 17N O 2Molar mass 195 262 g mol 1PharmacologyLegal status AU S9 Prohibited substance BR Class F2 Prohibited psychotropics NZ Class A US Schedule IExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references 2 5 DMA is the alpha methyl homologue of 2C H and could be called DOH under the DO naming scheme Dosage 80 160 mg 2 Duration 6 8 hours Effects Mydriasis 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 3 4 DMA Edit 3 4 Dimethoxyamphetamine NamesIUPAC name 1 3 4 dimethoxyphenyl propan 2 amineIdentifiersCAS Number 120 26 3Abbreviations 3 4 DMAChEMBL ChEMBL277540ChemSpider 8116EC Number 204 383 7PubChem CID 8423UNII EMH5PUB78VInChI InChI 1S C11H17NO2 c1 8 12 6 9 4 5 10 13 2 11 7 9 14 3 h4 5 7 8H 6 12H2 1 3H3Key KAZPHAGSWZTKDW UHFFFAOYSA NPropertiesChemical formula C 11H 17N O 2Molar mass 195 262 g mol 1PharmacologyLegal status AU S9 Prohibited substance BR Class F2 Prohibited psychotropics NZ Class A US Schedule IExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references 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 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 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 Legal status EditUnited States Edit 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 4 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 Edit DMA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard October 2015 5 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 5 New Zealand Edit DMA is considered a Class A controlled drug under the Misuse of Drugs Act 1975 6 See also Edit2 5 dimethoxyphenethylamine 2C H Trimethoxyamphetamine TMA 3 Methoxyamphetamine 4 MethoxyamphetamineReferences Edit a b c Shulgin Alexander Shulgin Ann September 1991 PiHKAL A Chemical Love Story Berkeley California Transform Press ISBN 0 9630096 0 5 OCLC 25627628 PiHKAL isomerdesign com Retrieved 2012 03 17 Baltzly Richard Buck Johannes S 1940 Amines Related to 2 5 Dimethoxyphenethylamine Journal of the Chemical Society 62 161 164 doi 10 1021 ja01858a046 1308 11 Schedule I Archived from the original on 2009 08 27 Retrieved 2014 12 21 a b Poisons Standard October 2015 https www comlaw gov au Details F2015L01534 Misuse of Drugs Act 1975 New Zealand Government Retrieved 2016 01 18 External links Edit2 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 Retrieved from https en wikipedia org w index php title Dimethoxyamphetamine amp oldid 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