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2,6-Dimethoxyamphetamine

2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families. It is one of the positional isomers of dimethoxyamphetamine.

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Jun 20, 2026
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2,6-Dimethoxyamphetamine
Clinical data
Other names2,6-DMA; DMA-5
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 1-(2,6-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=CC=C1OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)7-9-10(13-2)5-4-6-11(9)14-3/h4-6,8H,7,12H2,1-3H3
  • Key:OHGNLLDQBKOWJW-UHFFFAOYSA-N

2,6-Dimethoxyamphetamine (2,6-DMA), also known as DMA-5, is a drug of the phenethylamine and amphetamine families.1 It is one of the positional isomers of dimethoxyamphetamine.1

The drug has not been tested in humans and its effects in humans are unknown.1

2,6-DMA showed very low affinity for serotonin receptors in rat stomach fundus strips (A2 = 8,130 nM).12 In a subsequent study, it showed no affinity for the serotonin 5-HT2A or 5-HT2C receptors (Ki = >10,000 nM).3 2,6-DMA only partially substituted for DOM in rodent drug discrimination tests, with a maximum responding of 41% and behavioral disruption at higher doses.45 It did not substitute for dextroamphetamine in these tests.56

The chemical synthesis of 2,6-DMA has been described.1

2,6-DMA was first described in the scientific literature by Alexander Shulgin by 1969.7 At that time, he had not yet synthesized it and did not report its effects.7 2,6-DMA is a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA) and hence is a Schedule I controlled substance in the United States.1

See also

See also

References

References

  1. Shulgin A, Manning T, Daley PF (2011). "#37. 2,6-DMA". The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 63–65. ISBN 978-0-9630096-3-0. OCLC 709667010.
  2. Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". J Med Chem. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  3. 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.
  4. 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.
  5. Glennon RA (June 1986). "Discriminative stimulus properties of phenylisopropylamine derivatives". Drug Alcohol Depend. 17 (2–3): 119–134. doi:10.1016/0376-8716(86)90003-7. PMID 2874967.
  6. Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.
  7. Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297.
External links