Chemistry:MMDA-3b

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MMDA-3b, also known as 4-methoxy-2,3-methylenedioxyamphetamine (4-MeO-2,3-MDA), is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to ORTHO-MDA (2,3-MDA).[1][2] It is the 4-methoxy derivative of ORTHO-MDA and is a positional isomer of MMDA (5-MeO-3,4-MDA) and related compounds like MMDA-2 (6-MeO-3,4-MDA) and MMDA-3a (2-MeO-3,4-MDA).[2]

MMDA-3b was included as an entry in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[2] He lists its dose as greater than 80 mg orally and its duration as unknown.[2][3] Shulgin describes 60 mg as being definitely active, qualitatively like 3,4-methylenedioxyamphetamine (MDA), but quantitatively perhaps less, whereas an 80 mg dose of MMDA-3b was said to be no more effective than the 60 mg dose.[2] He also says that it is similar at these doses to 20 mg MMDA-3a and may be about 3-fold less potent than MMDA-3a.[2] Elsewhere, MMDA-3b is described as 3-fold more potent than mescaline.[4] Little is known about the drug.[2] The chemical synthesis of MMDA-3b was also described in PiHKAL.[2]

MMDA-3b has been found to act as an efficacious serotonin releasing agent with little effect on dopamine similarly to MMDA.[5] For comparison, MDA and MDMA release both serotonin and dopamine, whereas MMDA-2 releases neither serotonin nor dopamine.[5]

MMDA-3b was first described in the scientific literature by Shulgin in 1964.[6] It was subsequently described in greater detail by Shulgin in his book PiHKAL in 1991.[2] Other 2,3-MDA positional isomers of MMDA-3b include MMDA-4 and MMDA-5.[1][2]

MMDA-3b is a controlled substance in Canada under phenethylamine blanket-ban language.[7]

See also

References

  1. ↑ 1.0 1.1 Shulgin, Alexander T. (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. p. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. http://link.springer.com/10.1007/978-1-4757-0510-2_6. Retrieved 11 November 2025. 
  2. ↑ 2.00 2.01 2.02 2.03 2.04 2.05 2.06 2.07 2.08 2.09 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  https://erowid.org/library/books_online/pihkal/pihkal135.shtml
  3. ↑ "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". Hallucinogens: An Update. National Institute on Drug Abuse Research Monograph Series. 146. National Institute on Drug Abuse. 1994. pp. 74–91. https://bibliography.maps.org/resources/download/11534. 
  4. ↑ Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "A more extensive study (Shulgin, 1964b) confirmed these findings and suggested that the activities of 2-methoxy-4,5-methylenedioxyamphetamine (3.19) and 2-methoxy-3,4-methylenedioxyamphetamine (3.20) were as high as 21 and 18 times that of mescaline although these figures have been revised to 12 and 10, respectively (Shulgin and others, 1969). Activity is somewhat reduced when the methylenedioxy group is in other positions, 2,3-methylenedioxy-4-methoxyamphetamine (3.21) being only three times as potent as mescaline, and the importance of the 2-methoxy group in the series is again emphasized by the low equipotency of 3,4-methylenedioxyamphetamine (3.17) and 3-methoxy-4,5-methylenedioxyamphetamine (3.18) compared to the high potency of compounds containing this substituent (3.19, 3.20) (Table 3.4). Most of these compounds produce a typical mescaline syndrome, particularly of closed-eye imagery (Shulgin, Sargent, and Naranjo, 1973), [...]" 
  5. ↑ 5.0 5.1 "3,4-Methylenedioxyamphetamine (MDA) analogues exhibit differential effects on synaptosomal release of 3H-dopamine and 3H-5-hydroxytryptamine". Pharmacol Biochem Behav 38 (3): 505–512. March 1991. doi:10.1016/0091-3057(91)90005-m. PMID 1829838. 
  6. ↑ "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia 20 (7): 366–367. July 1964. doi:10.1007/BF02147960. PMID 5855670. 
  7. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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