3,5-Dimethoxyamphetamine

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).^[1] It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines).^[1]

3,5-Dimethoxyamphetamine

Clinical data
Other names	3,5-DMA; DMA-6
Identifiers
IUPAC name 1-(3,5-dimethoxyphenyl)propan-2-amine
CAS Number	15402-82-1
PubChem CID	91247
ChemSpider	82397
UNII	4U6LN22RX4
CompTox Dashboard (EPA)	DTXSID201345742
Chemical and physical data
Formula	C11H17NO2
Molar mass	195.262 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC(=CC(=C1)OC)OC)N
InChI 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

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.^[1][2] However, in a later study, it showed no or very low affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = >10,000 nM), whereas DOB showed high affinity for these receptors (K_i = 32 nM and 64 nM, respectively).^[3] 3,5-DMA's effects on monoamine reuptake and efflux have also been studied.^[1][4][5][6] It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent.^[4][5] 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).^[6]

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.^[1][7] However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.^[8] The effects of 3,5-DMA in humans have not been reported.^[1][8] 3,5-DMA has been detected as an adulterant in forensic drug samples.^[9] 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.^[1]

A derivative of 3,5-DMA, 4-bromo-3,5-dimethoxyamphetamine (4-Br-3,5-DMA), showed relatively high affinity for the serotonin 5-HT_2A and 5-HT_2C receptors (K_i = 210 nM and 570 nM, respectively).^[3] However, it was not active as a psychedelic at the assessed doses (4–10 mg).^[10]

See also

• Dimethoxyamphetamine
• 3C (psychedelics)
• 3,5-Dimethoxyphenethylamine (3,5-DMPEA)