2,3-Dimethoxyamphetamine
Pharmaceutical compound
From Wikipedia, the free encyclopedia
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]
- None
| |
| Clinical data | |
|---|---|
| Other names | 2,3-DMA; DMA-2; NSC-172189 |
| Drug class | Serotonin receptor modulator |
| ATC code |
|
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C11H17NO2 |
| Molar mass | 195.262 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
2,3-DMA does not appear to have been tested in humans.[1][2][3]
The drug showed weak affinity for serotonin receptors in rat stomach fundus strips (A2 = 2,880 nM).[4] 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).[5] It did not show activity as a norepinephrine releasing agent in vitro.[6] The drug is behaviorally active in mice.[2] 2,3-DMA did not substitute for DOM in rodent drug discrimination tests.[1][3] 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]
The chemical synthesis of 2,3-DMA has been described.[1]
2,3-DMA was first described in the scientific literature by F. Benington and colleagues by 1968.[1][6] Alexander Shulgin first described 2,3-DMA in 1969 but had not yet synthesized it and did not report its effects.[10]