2,3-Dimethoxyamphetamine

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2,3-Dimethoxyamphetamine
File:2,3-Dimethoxyamphetamine.svg
Clinical data
Other names2,3-DMA; DMA-2; NSC-172189
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(2,3-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C(=CC=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)7-9-5-4-6-10(13-2)11(9)14-3/h4-6,8H,7,12H2,1-3H3
  • Key:DHLWJXGSZDJWKK-UHFFFAOYSA-N

2,3-Dimethoxyamphetamine (2,3-DMA), also known as DMA-2, is a drug of the phenethylamine and amphetamine families.[1][2] It is one of the positional isomers of dimethoxyamphetamine.[1]

The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A2 = 2,880 nM).[3] In a subsequent study, 2,3-DMA showed very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 4,280 nM and >10,000 nM, respectively).[4] It did not show activity as a norepinephrine releasing agent in vitro.[5] The drug is behaviorally active in mice.[2] 2,3-DMA did not substitute for DOM in rodent drug discrimination tests.[1][6] However, it did partially substitute for 5-MeO-DMT in these tests.[1][7] As with DOM, the drug did not substitute for dextroamphetamine in drug discrimination tests.[8][9] It produced behavioral disruption at higher doses.[8][9] 2,3-DMA does not appear to have been tested in humans.[1][2][6]

2,3-DMA was first described in the scientific literature by 1968.[1][5] Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects.[10]

See also

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References

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