MMDA

Clinical data
Other names	3-Methoxy-4,5-methylenedioxyamphetamine; 5-Methoxy-MDA; 5-MeO-MDA
Routes of administration	Oral[1]
Drug class	Serotonin5-HT2A receptoragonist;Serotonin releasing agent;Serotonergic psychedelic;Hallucinogen;Entactogen
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class F2 (Prohibited psychotropics)[2] CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I UN: Psychotropic Schedule I
Pharmacokinetic data
Onset of action	20–45 minutes[1]
Identifiers
IUPAC name 1-(7-Methoxy-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number	13674-05-0
PubChemCID	26175
ChemSpider	24386
UNII	RG7FY73ZAA
KEGG	C22812 Y
CompTox Dashboard(EPA)	DTXSID50860757
Chemical and physical data
Formula	C11H15NO3
Molar mass	209.245 g·mol−1
3D model (JSmol)	Interactive image
SMILES O1c2cc(cc(OC)c2OC1)CC(N)C

MMDA, also known as3-methoxy-4,5-methylenedioxyamphetamine or as5-methoxy-MDA, is apsychedelic andentactogen of theamphetamine family.^[1]

MMDA was described byAlexander Shulgin in his bookPiHKAL.^[1] Shulgin lists the dosage range of MMDA as 100 to 250 mg.^[1] The first effects appear within 20 to 45 minutes followingoral administration.^[1] Itsduration is described as "moderate".^[1]

MMDA produces effects includingrelaxation,time dilation,empathy,passivity,compassion, changes inmusic perception,closed-eye visuals such as geometric patterns,open-eye visuals,dream-like states described as "brain movies", and anafterglow.^[1][3] It has been said to be gentler than certain other psychedelics.^[1] The drug is said to have similar effects toMDA, but to be to some extent more psychedelic in comparison.^[3]

Side effects of MMDA have been reported to includerestlessness,cold sensations,shivering,nausea,abdominal cramps,disorientation,social withdrawal,feeling ill, andanxiety.^[1]

MMDA has been shown to act as a non-neurotoxicserotonin releasing agent, with no effects on release ofdopamine or probablynorepinephrine,^[4] and as aserotonin5-HT_2A receptoragonist.^[5] The latter property is thought to be responsible for itspsychedelic effects, whereas the former action may be involved in itsentactogenic effects.^[4][5]

MMDA has been found to be formed frommyristicin, a component ofnutmeg, in rabbits and rats.^[1][6] However, MMDA could not be detected with nutmeg misuse in a human.^[7]

Analogues of MMDA includelophophine (MMDPEA),MDA,MDMA, andTMA.^[1]Positional isomers of MMDA includeMMDA-2,MMDA-3a,MMDA-3b,MMDA-4, andMMDA-5.^[1] Further analogues andderivatives of MMDA includeDMMDA,DMMDA-2,DMMDA-3,DMMDA-4,DMMDA-5, andDMMDA-6.^[1]

MMDA was firstsynthesized and studied byGordon Alles at theEdgewood Arsenal in the mid-1950s.^[8] Its Edgewood Arsenal code name is unknown.^[8] Subsequently,Alexander Shulgin synthesized MMDA in 1962 and discovered itspsychoactive effects that same year.^[9][10] Shulgin published his findings on MMDA in thescientific literature in 1964.^{[9][10][11][12]} Use of MMDA inpsychedelic-assisted psychotherapy was studied by Shulgin, Thornton Sargent, andClaudio Naranjo in the mid-1960s and their findings were published in 1973.^[9][13] Naranjo also described MMDA for these purposes in his 1973 bookThe Healing Journey: New Approaches to Consciousness.^[14] Shulgin subsequently further described MMDA in his bookPiHKAL in 1991.^[1]

Internationally, MMDA is a Schedule I drug under theConvention on Psychotropic Substances.^[15]

MMDA is considered a Schedule 9 prohibited substance in Australia under thePoisons Standard (October 2015).^[16] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.^[16]

MMDA is classified as aSchedule 1 substance in the United States, and is similarly controlled in other parts of the world. MMDA remains illegal, however it is classified differently than the illegality of MDMA.^{[citation needed]}

• Substituted methylenedioxyphenethylamine
• Substituted methoxyphenethylamine
• Methoxymethylenedioxyamphetamine
• Dimethoxymethylenedioxyamphetamine

• MMDA - Isomer Design
• MMDA - PiHKAL - Erowid
• MMDA - PiHKAL - Isomer Design

• Drugs not assigned an ATC code
• 5-HT2A agonists
• Alexander Shulgin
• Designer drugs
• Entactogens
• Methoxyphenethylamines
• Methylenedioxyphenethylamines
• Phenol ethers
• Psychedelic phenethylamines
• Serotonin receptor agonists
• Serotonin releasing agents
• Substituted amphetamines

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