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MMDA-3b

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MMDA-3b
Clinical data
Other names4-MeO-2,3-MDA; 4-Methoxy-2,3-methylenedioxyamphetamine; 2,3-Methylenedioxy-4-methoxyamphetamine; 4-Methoxy-ORTHO-MDA; 4-MeO-ORTHO-MDA
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen; Serotonin releasing agent
ATC code
  • None
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • 1-(7-methoxy-1,3-benzodioxol-4-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H15NO3
Molar mass209.245 g·mol−1
3D model (JSmol)
  • CC(CC1=C2C(=C(C=C1)OC)OCO2)N
  • InChI=1S/C11H15NO3/c1-7(12)5-8-3-4-9(13-2)11-10(8)14-6-15-11/h3-4,7H,5-6,12H2,1-2H3
  • Key:CLRZDDLQTLKYFH-UHFFFAOYSA-N

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).[2][1] 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).[1]

MMDA-3b was included as an entry in Alexander Shulgin's book PiHKAL (Phenethylamines I Have Known and Loved).[1] He lists its dose as greater than 80 mg orally and its duration as unknown.[1][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.[1] 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.[1] Elsewhere, MMDA-3b is described as 3-fold more potent than mescaline.[4] Little is known about the drug.[1] The chemical synthesis of MMDA-3b was also described in PiHKAL.[1]

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.[1] Other 2,3-MDA positional isomers of MMDA-3b include MMDA-4 and MMDA-5.[2][1]

See also

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References

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  1. ^ a b c d e f g h i j k l m Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal135.shtml
  2. ^ a b 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. Retrieved 11 November 2025.
  3. ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on 13 July 2025.
  4. ^ Brimblecombe RW, Pinder RM (1975). Hallucinogenic Agents. Bristol: Wright-Scientechnica. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. 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. ^ 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". Pharmacol Biochem Behav. 38 (3): 505–512. doi:10.1016/0091-3057(91)90005-m. PMID 1829838.
  6. ^ Shulgin AT (July 1964). "Psychotomimetic amphetamines: methoxy 3,4-dialkoxyamphetamines". Experientia. 20 (7): 366–367. doi:10.1007/BF02147960. PMID 5855670.
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