MMDA (drug)

MMDA was described by Alexander Shulgin in his book PiHKAL. Shulgin lists the dosage range of MMDA as 100 to 250{{nbsp}}mg. The first effects appear within 20 to 45{{nbsp}}minutes following oral administration. Its duration is described as "moderate".

MMDA produces effects including relaxation, time dilation, empathy, passivity, compassion, changes in music perception, closed-eye visuals such as geometric patterns, open-eye visuals, dream-like states described as "brain movies", and an afterglow. It has been said to be gentler than certain other psychedelics. The drug is said to have similar effects to MDA, but to be to some extent more psychedelic in comparison.{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines | journal = Psychopharmacol Bull | volume = 4 | issue = 3 | pages = 13 | date = December 1967 | pmid = 5615546 | doi = | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=a15476299fba3b3a535958d0b198e813816ce768 | quote = The psychotropic effects of MMDA are rather similar to those of MDA, but in addition some 30% of the subjects reported rather vivid and well structured visual images appearing when the eyes are closed, although there are virtually no changes in eyes-open perception.}}

Side effects of MMDA have been reported to include restlessness, cold sensations, shivering, nausea, abdominal cramps, disorientation, social withdrawal, feeling ill, and anxiety.

{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

MMDA has been shown to act as a non-neurotoxic serotonin releasing agent, with no effects on release of dopamine or probably norepinephrine,{{cite journal |vauthors=McKenna DJ, Guan XM, Shulgin AT | title = 3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine | journal = Pharmacology Biochemistry and Behavior | volume = 38 | issue = 3 | pages = 505–12 |date=March 1991 | pmid = 1829838 | doi = 10.1016/0091-3057(91)90005-M| s2cid = 2740262 | doi-access = free }} and as a serotonin 5-HT_2A receptor agonist.{{cite journal |vauthors=Zhang Z, An L, Hu W, Xiang Y | title = 3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach | journal = Journal of Computer-aided Molecular Design | volume = 21 | issue = 4 | pages = 145–53 |date=April 2007 | pmid = 17203365 | doi = 10.1007/s10822-006-9090-y | bibcode = 2007JCAMD..21..145Z | s2cid = 25343432 }} The latter property is thought to be responsible for its psychedelic effects, whereas the former action may be involved in its entactogenic effects.

MMDA has been found to be formed from myristicin, a component of nutmeg, in rabbits and rats.{{cite journal | vauthors = Braun U, Kalbhen DA | title = Evidence for the biogenic formation of amphetamine derivatives from components of nutmeg | journal = Pharmacology | volume = 9 | issue = 5 | pages = 312–316 | date = 1973 | pmid = 4737998 | doi = 10.1159/000136402 | url = }} However, MMDA could not be detected with nutmeg misuse in a human.{{cite journal | vauthors = Beyer J, Ehlers D, Maurer HH | title = Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry | journal = Ther Drug Monit | volume = 28 | issue = 4 | pages = 568–575 | date = August 2006 | pmid = 16885726 | doi = 10.1097/00007691-200608000-00013 | url = }}

Analogues of MMDA include lophophine (MMDPEA), MDA, MDMA, and TMA. Positional isomers of MMDA include MMDA-2, MMDA-3a, MMDA-3b, MMDA-4, and MMDA-5. Further analogues and derivatives of MMDA include DMMDA, DMMDA-2, DMMDA-3, DMMDA-4, DMMDA-5, and DMMDA-6.

MMDA was first synthesized and studied by Gordon Alles at the Edgewood Arsenal in the mid-1950s.{{cite journal | vauthors = Passie T, Benzenhöfer U | title = MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s) | journal = Drug Test Anal | volume = 10 | issue = 1 | pages = 72–80 | date = January 2018 | pmid = 28851034 | doi = 10.1002/dta.2292 | url = https://psychedelic-science.org/fileadmin/user_upload/10_Passie_Benzenho__fer_MDMA_and_the_military_DTA_2017_Kopie.pdf}} Its Edgewood Arsenal code name is unknown. Subsequently, Alexander Shulgin synthesized MMDA in 1962 and discovered its psychoactive effects that same year.{{cite journal | vauthors = Benzenhöfer U, Passie T | title = Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin | journal = Addiction | volume = 105 | issue = 8 | pages = 1355–61 | date = August 2010 | pmid = 20653618 | doi = 10.1111/j.1360-0443.2010.02948.x | url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=9f771291da5334de52f9369c649927d331d09151| url-access = subscription }}{{cite journal | last=Shulgin | first=Alexander T. | title=Profiles of Psychedelic Drugs: MMDA | journal=Journal of Psychedelic Drugs | volume=8 | issue=4 | date=1976 | issn=0022-393X | doi=10.1080/02791072.1976.10471859 | pages=331–331}} Shulgin published his findings on MMDA in the scientific literature in 1964.{{cite journal | vauthors = Shulgin AT | title = 3-Methoxy-4 5-methylenedioxy Amphetamine, a New Psychotomimetic Agent | journal = Nature | volume = 201 | issue = | pages = 1120–1121 | date = March 1964 | pmid = 14152788 | doi = 10.1038/2011120a0 | url = }}{{cite journal | vauthors = Shulgin AT | title = Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines | journal = Experientia | volume = 20 | issue = 7 | pages = 366–367 | date = July 1964 | pmid = 5855670 | doi = 10.1007/BF02147960 | url = }} Use of MMDA in psychedelic-assisted psychotherapy was studied by Shulgin, Thornton Sargent, and Claudio Naranjo in the mid-1960s and their findings were published in 1973.{{cite journal | vauthors = Shulgin AT, Sargent T, Naranjo C | title = Animal pharmacology and human psychopharmacology of 3-methoxy-4,5-methylenedioxyphenylisopropylamine (MMDA) | journal = Pharmacology | volume = 10 | issue = 1 | pages = 12–18 | date = 1973 | pmid = 4751535 | doi = 10.1159/000136416 | url = }} Naranjo also described MMDA for these purposes in his 1973 book The Healing Journey: New Approaches to Consciousness.{{cite book | last=Naranjo | first=Claudio | title=The Healing Journey: New Approaches to Consciousness | publisher=Pantheon Books | date=1974 | isbn=978-0-394-48826-4 | url=https://books.google.com/books?id=IKwoPwAACAAJ | access-date=28 April 2025 | archive-url=https://archive.org/details/healingjourneyne00nara | archive-date=25 February 2011}} Shulgin subsequently further described MMDA in his book PiHKAL in 1991.

Internationally, MMDA is a Schedule I drug under the Convention on Psychotropic Substances.{{cite web|url=http://www.incb.org/pdf/e/list/green.pdf |title=Archived copy |access-date=2005-11-19 |url-status=dead |archive-url=https://web.archive.org/web/20051205125434/http://www.incb.org/pdf/e/list/green.pdf |archive-date=2005-12-05 }}

MMDA is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534 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.

MMDA is classified as a Schedule 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|date=April 2025}}

• Substituted methylenedioxyphenethylamine
• Substituted methoxyphenethylamine
• Methoxymethylenedioxyamphetamine
• Dimethoxymethylenedioxyamphetamine

{{Reflist}}

• [https://isomerdesign.com/pihkal/explore/132 MMDA - Isomer Design]
• [https://www.erowid.org/library/books_online/pihkal/pihkal132.shtml MMDA - PiHKAL - Erowid]
• [http://pihkal.info/read.php?domain=pk&id=132 MMDA - PiHKAL - Isomer Design]

{{Psychedelics}}

{{Entactogens}}

{{Serotonin receptor modulators}}

{{Monoamine releasing agents}}

{{Phenethylamines}}

{{Chemical classes of psychoactive drugs}}

{{DEFAULTSORT:Methoxy-4,5-methylendioxyamphetamine, 3-}}

Category:5-HT2A agonists

Category:Alexander Shulgin

Category:Designer drugs

Category:Entactogens

Category:Methoxyphenethylamines

Category:Methylenedioxyphenethylamines

Category:Phenol ethers

Category:Psychedelic phenethylamines

Category:Serotonin receptor agonists

Category:Serotonin releasing agents

Category:Substituted amphetamines