Article · Wikipedia archive · Last revised Jun 18, 2026

MMDA-2

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families. It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).

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MMDA-2
Clinical data
Other names2-Methoxy-4,5-methylenedioxyamphetamine; 6-Methoxy-3,4-methylenedioxyamphetamine; 6-Methoxy-MDA; 6-MeO-MDA
Routes of
administration		Oral1
Drug classSerotonin 5-HT2 receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action8–12 hours1
Identifiers
  • 1-(6-methoxy-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H15NO3
Molar mass209.245 g·mol−1
3D model (JSmol)
  • O1c2cc(c(OC)cc2OC1)CC(N)C

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families.12 It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).12

Use and effects

In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MMDA-2's dose as 25 to 50 mg orally and its duration as 8 to 12 hours.12 The effects of MMDA-2 have been reported to include enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss.1 Shlgin states that MMDA-2 at a dose of 30 mg orally is very similar to MDA at a dose of 80 mg orally, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.1 MMDA-2 is approximately 4- or 5-fold more potent than MMDA, which has a listed dose range of 100 to 250 mg orally.1

Interactions

Pharmacology

Pharmacodynamics

MMDA-2 is a moderately potent serotonin receptor agonist in the rat stomach fundus assay (A2 = 224 nM).3 These serotonin receptors may correspond specifically to the serotonin 5-HT2B receptor.45

It has been found that MMDA-2, unlike MMDA but similarly to 6-methyl-MDA, is very weak or negligible at inducing the release of serotonin or dopamine in vitro.6 Accordingly, it does not produce amphetamine-like responses in animals in drug discrimination studies.7 Instead, MMDA-2 is likely to act as a pure serotonin 5-HT2 receptor agonist similarly to the DOx series of compounds, with activation of the serotonin 5-HT2A receptor believed to be responsible for its psychedelic effects.8

Chemistry

Synthesis

The chemical synthesis of MMDA-2 has been described.1

Analogues

Analogues of MMDA-2 include 2C-MMDA-2 (MMDPEA-2; 6-methoxy-MDPEA), MDA, MMDA (5-methoxy-MDA), MMDA-3a (2-methoxy-MDA), DMMDA-2 (5,6-dimethoxy-MDA; 5-methoxy-MMDA-2), methyl-MMDA-2 (N-methyl-MMDA-2; 6-methoxy-MDMA), EMDA-2 (6-ethoxy-MDA; 6-ethoxy-MMDA-2), 2C2-NBOMe (2C-MMDA-2-NBOMe; NBOMe-MMDPEA-2), F (5-methoxy-6-APDB), 4T-MMDA-2 (4-thio-MMDA-2), 6-methyl-MDA, 6-bromo-MDA (2-Br-4,5-MDA), and 6-chloro-MDA (2-Cl-4,5-MDA), among others.12

History

MMDA-2 was first described in the scientific literature by Alexander Shulgin in 1964.9 Subsequently, it was described in greater detail by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.1 MMDA-2 was encountered as a novel designer drug by the 1990s.1011

Society and culture

Canada

MMDA-2 may be a controlled substance in Canada under phenethylamine blanket-ban language.12

United States

MMDA-2 is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of MMDA.1314

See also

See also

References

References

  1. Shulgin A, Shulgin A (13 May 2016). "MMDA-2 (2-Methoxy-4,5-methylenedioxyamphetamine)". Pihkal: A Chemical Love Story. Transform Press. ISBN 978-0-9630096-0-9.
  2. Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. ISBN 978-3-03788-700-4. OCLC 858805226. Archived from the original on 21 August 2025.
  3. Glennon RA, Liebowitz SM, Anderson GM (March 1980). "Serotonin receptor affinities of psychoactive phenalkylamine analogues". Journal of Medicinal Chemistry. 23 (3): 294–299. doi:10.1021/jm00177a017. PMID 7365744.
  4. Baxter GS, Murphy OE, Blackburn TP (May 1994). "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". British Journal of Pharmacology. 112 (1): 323–331. doi:10.1111/j.1476-5381.1994.tb13072.x. PMC 1910288. PMID 8032658.
  5. Nichols DE, Schooler D, Yeung MC, Oberlender RA, Zabik JE (September 1984). "Unreliability of the rat stomach fundus as a predictor of hallucinogenic activity in substituted phenethylamines". Life Sciences. 35 (13): 1343–1348. doi:10.1016/0024-3205(84)90390-4. PMID 6482656.
  6. McKenna DJ, Guan XM, Shulgin AT (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology, Biochemistry, and Behavior. 38 (3): 505–512. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. S2CID 2740262.
  7. Glennon RA, Yousif M, Naiman N, Kalix P (March 1987). "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior. 26 (3): 547–551. doi:10.1016/0091-3057(87)90164-X. PMID 3575369. S2CID 5890314.
  8. Clare BW (2002). "QSAR of benzene derivatives: comparison of classical descriptors, quantum theoretic parameters and flip regression, exemplified by phenylalkylamine hallucinogens". Journal of Computer-Aided Molecular Design. 16 (8–9): 611–633. Bibcode:2002JCAMD..16..611C. doi:10.1023/A:1021966231380. PMID 12602954. S2CID 9948738.
  9. Shulgin AT (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia. 20 (7): 366–367. doi:10.1007/BF02147960. PMID 5855670. Archived from the original on 2025-07-12.
  10. King LA (1996). "Designer drugs related to amphetamine (1990-1996)". J Clan Lab Invest Chem Assoc. 6 (3): 15–16.
  11. Min JZ, Shimizu Y, Toyo'oka T, Inagaki S, Kikura-Hanajiri R, Goda Y (October 2008). "Simultaneous determination of 11 designated hallucinogenic phenethylamines by ultra-fast liquid chromatography with fluorescence detection". Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences. 873 (2): 187–194. doi:10.1016/j.jchromb.2008.08.020. PMID 18789774.
  12. "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
  13. Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
  14. Drug Enforcement Administration (3 December 2007). "Definition of "Positional Isomer" as It Pertains to the Control of Schedule I Controlled Substances". Federal Register.
External links