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MMDA (drug)

MMDA, also known as 3-methoxy-4,5-methylenedioxyamphetamine or as 5-methoxy-MDA, is a psychedelic and entactogen of the amphetamine family.[1]

Use and effects

MMDA was described by Alexander Shulgin in his book PiHKAL.[1] Shulgin lists the dosage range of MMDA as 100 to 250 mg.[1] The first effects appear within 20 to 45 minutes following oral administration.[1] Its duration is described as "moderate".[1]

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.[1][3] It has been said to be gentler than certain other psychedelics.[1] The drug is said to have similar effects to MDA, but to be to some extent more psychedelic in comparison.[3]

Side effects

Side effects of MMDA have been reported to include restlessness, cold sensations, shivering, nausea, abdominal cramps, disorientation, social withdrawal, feeling ill, and anxiety.[1]

Interactions

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

MMDA has been shown to act as a non-neurotoxic serotonin releasing agent, with no effects on release of dopamine or probably norepinephrine,[4] and as a serotonin 5-HT2A receptor agonist.[5] The latter property is thought to be responsible for its psychedelic effects, whereas the former action may be involved in its entactogenic effects.[4][5]

Pharmacokinetics

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

Chemistry

Analogues of MMDA include lophophine (MMDPEA), MDA, MDMA, and TMA.[1] Positional isomers of MMDA include MMDA-2, MMDA-3a, MMDA-3b, MMDA-4, and MMDA-5.[1] Further analogues and derivatives of MMDA include DMMDA, DMMDA-2, DMMDA-3, DMMDA-4, DMMDA-5, and DMMDA-6.[1]

History

MMDA was first synthesized and studied by Gordon Alles at the Edgewood Arsenal in the mid-1950s.[8] Its Edgewood Arsenal code name is unknown.[8] Subsequently, Alexander Shulgin synthesized MMDA in 1962 and discovered its psychoactive effects that same year.[9][10] Shulgin published his findings on MMDA in the scientific literature in 1964.[9][10][11][12] 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.[9][13] Naranjo also described MMDA for these purposes in his 1973 book The Healing Journey: New Approaches to Consciousness.[14] Shulgin subsequently further described MMDA in his book PiHKAL in 1991.[1]

Society and culture

International

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

Australia

MMDA is considered a Schedule 9 prohibited substance in Australia under the Poisons 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]

United States

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]

See also

References

  1. ^ a b c d e f g h i j k l m n o Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ a b Shulgin AT, Sargent T, Naranjo C (December 1967). "The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines". Psychopharmacol Bull. 4 (3): 13. PMID 5615546. 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.
  4. ^ a b 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): 505–12. doi:10.1016/0091-3057(91)90005-M. PMID 1829838. S2CID 2740262.
  5. ^ a b Zhang Z, An L, Hu W, Xiang Y (April 2007). "3D-QSAR study of hallucinogenic phenylalkylamines by using CoMFA approach". Journal of Computer-aided Molecular Design. 21 (4): 145–53. Bibcode:2007JCAMD..21..145Z. doi:10.1007/s10822-006-9090-y. PMID 17203365. S2CID 25343432.
  6. ^ Braun U, Kalbhen DA (1973). "Evidence for the biogenic formation of amphetamine derivatives from components of nutmeg". Pharmacology. 9 (5): 312–316. doi:10.1159/000136402. PMID 4737998.
  7. ^ Beyer J, Ehlers D, Maurer HH (August 2006). "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". Ther Drug Monit. 28 (4): 568–575. doi:10.1097/00007691-200608000-00013. PMID 16885726.
  8. ^ a b Passie T, Benzenhöfer U (January 2018). "MDA, MDMA, and other "mescaline-like" substances in the US military's search for a truth drug (1940s to 1960s)" (PDF). Drug Test Anal. 10 (1): 72–80. doi:10.1002/dta.2292. PMID 28851034.
  9. ^ a b c Benzenhöfer U, Passie T (August 2010). "Rediscovering MDMA (ecstasy): the role of the American chemist Alexander T. Shulgin". Addiction. 105 (8): 1355–61. doi:10.1111/j.1360-0443.2010.02948.x. PMID 20653618.
  10. ^ a b Shulgin, Alexander T. (1976). "Profiles of Psychedelic Drugs: MMDA". Journal of Psychedelic Drugs. 8 (4): 331–331. doi:10.1080/02791072.1976.10471859. ISSN 0022-393X.
  11. ^ Shulgin AT (March 1964). "3-Methoxy-4 5-methylenedioxy Amphetamine, a New Psychotomimetic Agent". Nature. 201: 1120–1121. doi:10.1038/2011120a0. PMID 14152788.
  12. ^ Shulgin AT (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia. 20 (7): 366–367. doi:10.1007/BF02147960. PMID 5855670.
  13. ^ Shulgin AT, Sargent T, Naranjo C (1973). "Animal pharmacology and human psychopharmacology of 3-methoxy-4,5-methylenedioxyphenylisopropylamine (MMDA)". Pharmacology. 10 (1): 12–18. doi:10.1159/000136416. PMID 4751535.
  14. ^ Naranjo, Claudio (1974). The Healing Journey: New Approaches to Consciousness. Pantheon Books. ISBN 978-0-394-48826-4. Archived from the original on 25 February 2011. Retrieved 28 April 2025.
  15. ^ "Archived copy" (PDF). Archived from the original (PDF) on 2005-12-05. Retrieved 2005-11-19.{{cite web}}: CS1 maint: archived copy as title (link)
  16. ^ a b Poisons Standard October 2015 https://www.comlaw.gov.au/Details/F2015L01534