MMDA-5

MMDA-5
Clinical data
Other names6-Methoxy-2,3-methylenedioxyamphetamine; 6-Methoxy-2,3-MDA; 6-Methoxy-ORTHO-MDA
Routes of
administration		Oral
Drug classPsychoactive drug
ATC code
  • None
Identifiers
  • 1-(5-methoxy-1,3-benzodioxol-4-yl)propan-2-amine
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC11H15NO3
Molar mass209.245 g·mol−1
3D model (JSmol)
  • CC(CC1=C(C=CC2=C1OCO2)OC)N
  • InChI=1S/C11H15NO3/c1-7(12)5-8-9(13-2)3-4-10-11(8)15-6-14-10/h3-4,7H,5-6,12H2,1-2H3
  • Key:CMLBFORYSUACKE-UHFFFAOYSA-N

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

Alexander Shulgin briefly mentions MMDA-5 in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications. According to Shulgin, MMDA-5 has been very sparsely explored in humans. In any case, he described two experience reports with it that had been communicated to him. The first, at 30 mg orally, was said to be modestly active but not a particularly pleasant experience, whereas the other was at 15 mg orally but whether there were any effects was not mentioned. Shulgin did not test MMDA-5 himself, and the effects of MMDA-5, for instance whether it produces hallucinogenic or stimulant effects, have not otherwise been described. Based on the 30 mg report, Shulgin concluded that MMDA-5 might have approximately 10 or 12 times the potency of mescaline.

The chemical synthesis of MMDA-5 has been described. Other 2,3-MDA positional isomers of MMDA-5 include MMDA-3b and MMDA-4.

MMDA-5 was first described in the scientific literature by Shulgin and colleagues in 1969. Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "The remaining MMDA-analogue that has been prepared, is the 2,3,6-isomer. The flow diagram started with sesamol (3,4-methylenedioxyphenol) which was methylated with methyl iodide, converted to the aldehyde using butyllithium and N-methylformanilide (putting the new group directly between the two oxygen atoms, giving 2,3-methylenedioxy-6-methoxybenzaldehyde), reaction with nitroethane to the nitrostyrene, and its reduction with lithium aluminum hydride in ether. The product, 6-methoxy-2,3-methylenedioxyamphetamine hydrochloride (MMDA-5) is practically unexplored in man. I have heard one report that 30 milligrams was modestly active, but not a particularly pleasant experience. Another person told me that he had tried 15 milligrams, but he neglected to mention if there had been any effects. I have not tried it myself. But, I have succumbed to the pressure of the experimental pharmacologists to give a number for the “Y-axis” of their animal behavior studies. So I said to myself, if this is active at 30 milligrams, and mescaline is active at 300 milligrams, why not say that it is 10× the activity of mescaline? So I did. But I have absolutely no confidence in that number."
  2. 1 2 3 4 5 6 7 8 Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. 3.2.9. 6-Methoxy-2,3-methylenedioxyphenylisopropylamine: Equally sparse human pharmacology has been reported for 6-methoxy2,3-methylenedioxyphenylisopropylamine (56, MMDA-5, 6-methoxy-2,3-methylenedioxyamphetamine) the methylenedioxyanalog of TMA-5. Its oral activity is realized at dosages of 30 mg (LaBerge, cited in Shulgin, 1973), which would suggest a potency perhaps ten times that of mescaline.
  3. 1 2 3 Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on 13 July 2025. Similarly, the second possible positional isomer of MMDA-3a is known (4-methoxy-2,3-methylenedioxyamphetamine, MMDA-3b) and has been clinically explored at up to 50mg without any central effects being noted. With the methylenedioxy in that 2,3-orientation, next to the amphetamine chain, two more isomers are possible. The 2,3,5-arrangement has been named MMDA-4 and the 2,3,6-counterpart is known as MMDA-5; no human activity for either compound has been reported in the literature. There cannot be, of course, a MMDA-6 as the 2,4,6 orientation lacks adjacent oxygen atoms.
  4. ↑ "ex. Mark Leon - MMDA-5" (PDF). isomerdesign.com.
  5. 1 2 Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. The fifth of these methoxy methylenedioxy isomers is 6-methoxy-2,3-methylenedioxyphenylisopropylamine [MMDA-5 (LXXVIII)] which corresponds exactly to TMA-5 (LXVI) both in substitution pattern and in potency (Shulgin, 1973b).
  6. ↑ Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  7. ↑ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
  8. ↑ Shulgin AT, Sargent T, Naranjo C (February 1969). "Structure--activity relationships of one-ring psychotomimetics". Nature. 221 (5180): 537–541. Bibcode:1969Natur.221..537S. doi:10.1038/221537a0. PMID 5789297. Archived from the original on 2025-07-12.
  9. ↑ Shulgin AT (March 1973). "Mescaline: the chemistry and pharmacology of its analogs". Lloydia. 36 (1): 46–58. PMID 4576313. Archived from the original on 2025-07-12. The fifth of these methoxy methylenedioxy isomers is 6-methoxy-2,3-methylenedioxyphenylisopropylamine (MMDA-5, 30) which corresponds exactly to TMA-5 (19) both in substitution pattern and in potency (42). [...] 42. LABERGE, S. 1972. Personal communication.