Article · Wikipedia archive · Last revised Jul 3, 2026

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). It is the parent structure of the 3C family of compounds.

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

Use and effects

The effects of 3,5-DMA in humans have not been reported.12

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.13 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).4

3,5-DMA's effects on monoamine reuptake and efflux have also been studied.1567 It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent.56 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).7

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.18 However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.2

Chemistry

Synthesis

The chemical synthesis of 3,5-DMA has been described.1

History

3,5-DMA was first described in the scientific literature by F. Benington and colleagues by at least 1968.5 It was not included as an entry in Alexander Shulgin's 1991 book PiHKAL (Phenethylamines I Have Known and Loved),9 but was subsequently included as an entry in his 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.1 The drug has been detected as an adulterant in forensic drug samples.10

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.1 It is also a controlled substance in Canada as an analogue of amphetamine. 11

See also

See also

References

References

  1. Shulgin A, Manning T, Daley PF (2011). "#39. 3,5-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 70–71. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. Brimblecombe RW, Pinder RM (1975). "Phenylalkylamines and Their Derivatives". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 55–97.
  3. Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues" (PDF). J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  4. Dowd CS, Herrick-Davis K, Egan C, DuPre A, Smith C, Teitler M, Glennon RA (August 2000). "1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT(2A) partial agonists". J Med Chem. 43 (16): 3074–3084. doi:10.1021/jm9906062. PMID 10956215.
  5. Benington F, Morin RD (July 1968). "The chemorelease of norepinephrine from mouse hearts by substituted amphetamines". J Med Chem. 11 (4): 896–897. doi:10.1021/jm00310a048. PMID 5677681.
  6. Paton DM (May 1975). "Effect of amphetamine, 3,4-methylenedioxyamphetamine, p-methoxyamphetamine and related amphetamines on uptake of metaraminol and efflux of noradrenaline in adrenergic nerves of rabbit atria". J Pharm Pharmacol. 27 (5): 361–362. doi:10.1111/j.2042-7158.1975.tb09456.x. PMID 239139.
  7. Tseng LF, Loh HH (April 1977). "Effects of methoxyamphetamines on the uptake and release of [3H]5-hydroxytryptamine by human blood platelets". Biochem Pharmacol. 26 (7): 647–649. doi:10.1016/0006-2952(77)90041-7. PMID 577148.
  8. Glennon RA, Young R (October 1982). "Comparison of behavioral properties of di- and tri-methoxyphenylisopropylamines". Pharmacol Biochem Behav. 17 (4): 603–607. doi:10.1016/0091-3057(82)90330-6. PMID 6965276.
  9. Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  10. Giné CV, Espinosa IF, Vilamala MV (2014). "New psychoactive substances as adulterants of controlled drugs. A worrying phenomenon?". Drug Test Anal. 6 (7–8): 819–24. doi:10.1002/dta.1610. PMID 24470121.
  11. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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