MMDA-2

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Psychedelic drug

title: "MMDA-2" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["designer-drugs", "methoxyphenethylamines", "methylenedioxyphenethylamines", "phenol-ethers", "pihkal", "psychedelic-phenethylamines", "serotonin-receptor-agonists", "substituted-amphetamines"] description: "Psychedelic drug" topic_path: "general/designer-drugs" source: "https://en.wikipedia.org/wiki/MMDA-2" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Psychedelic drug ::

| image = MMDA-2.svg | image_class = skin-invert-image | width = 225px | image2 = MMDA-2 ball-and-stick structure.png | image_class2 = bg-transparent | width2 = 225px

| tradename = | pregnancy_category = | routes_of_administration = Oral | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =

| legal_CA = Schedule I | legal_DE = NpSG | legal_UK = Class A | legal_status = Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)

| bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = 8–12 hours | excretion =

| CAS_number = 23693-18-7 | UNII_Ref = | UNII = TG0B6ER184 | PubChem = 90966 | ChemSpiderID = 82147 | synonyms = 2-Methoxy-4,5-methylenedioxyamphetamine; 6-Methoxy-3,4-methylenedioxyamphetamine; 6-Methoxy-MDA; 6-MeO-MDA

| IUPAC_name = 1-(6-methoxy-1,3-benzodioxol-5-yl)propan-2-amine | C=11 | H=15 | N=1 | O=3 | SMILES = 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. It is closely related to MMDA and MDA.

Alexander Shulgin was likely the first to synthesize MMDA-2. In his book PiHKAL (Phenethylamines I Have Known and Loved), the dose is listed as 25 to 50mg, and the duration is listed as 8 to 12hours. Shulgin reports that MMDA-2 produces effects such as enhanced awareness, empathy, and visual facilitation and distortion, as well as some side effects like gastrointestinal upset and appetite loss. He states that 30mg is very similar to 80mg of MDA, and also remarks that it would be impossible for anyone to have a bad experience on the drug at that dose.

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, and accordingly, does not produce amphetamine-like responses in animals in drug discrimination studies. 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 conferring its psychedelic effects.

MMDA-2 has been sold as a designer drug in Japan. It may be a controlled substance in Canada under phenethylamine blanket-ban language. The drug is not an explicitly controlled substance in the United States, but may be considered scheduled as an isomer of MMDA.

References

References

  1. (13 May 2016). "Pihkal: A Chemical Love Story". Transform Press.
  2. (March 1991). "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacology, Biochemistry, and Behavior.
  3. (March 1987). "Methcathinone: a new and potent amphetamine-like agent". Pharmacology, Biochemistry, and Behavior.
  4. (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.
  5. (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.
  6. "Controlled Drugs and Substances Act".
  7. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
  8. [[Drug Enforcement Administration]]. (3 December 2007). "Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances".

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designer-drugsmethoxyphenethylaminesmethylenedioxyphenethylaminesphenol-etherspihkalpsychedelic-phenethylaminesserotonin-receptor-agonistssubstituted-amphetamines