3,5-Dimethoxyamphetamine

3,5-Dimethoxyamphetamine
Clinical data
Other names3,5-DMA; DMA-6
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(3,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=CC(=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)4-9-5-10(13-2)7-11(6-9)14-3/h5-8H,4,12H2,1-3H3
  • Key:PDCLPGSYMZLLDX-UHFFFAOYSA-N

3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a drug of the amphetamine family and a positional isomer of dimethoxyamphetamine (DMA). It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines).

Use and effects

The properties and effects of 3,5-DMA in humans have not been reported.

Pharmacology

Pharmacodynamics

In an early study, it showed similar affinity for serotonin receptors as mescaline (3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than DOx (4-substituted 2,5-dimethoxyamphetamine) drugs like DOM, DOET, and DOB. However, in a later study, it showed no or very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = >10,000 nM), whereas DOB showed high affinity for these receptors (Ki = 32 nM and 64 nM, respectively).

3,5-DMA's effects on monoamine reuptake and efflux have also been studied. It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent. Likewise, it was a very weak serotonin reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration = 18,500 nM) and serotonin releasing agent (active at ≥10,000 nM).

3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5 mg/kg), suggesting that it would not be hallucinogenic in humans. However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.

Chemistry

Synthesis

The chemical synthesis of 3,5-DMA has been described.

History

3,5-DMA was first described in the scientific literature by F. Benington and colleagues by at least 1968. It was not included as an entry in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known and Loved), but was subsequently included as an entry in his 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. The drug has been detected as an adulterant in forensic drug samples.

Society and culture

As a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA; DMA-4), 3,5-DMA is a Schedule I controlled substance in the United States. It is also a controlled substance in Canada as an analogue of amphetamine.

See also