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[1]
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).[1][2] 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).[1][2][3]

Alexander Shulgin briefly mentions MMDA-5 in his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications.[1][2][3] According to Shulgin, MMDA-5 has been very sparsely explored in humans.[1][2][3] In any case, he described two experience reports with it that had been communicated to him.[1] 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.[1][2][4] 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.[1][2] Based on the 30 mg report, Shulgin concluded that MMDA-5 might have approximately 10 or 12 times the potency of mescaline.[1][5][2][6][7]

The chemical synthesis of MMDA-5 has been described.[1] Other 2,3-MDA positional isomers of MMDA-5 include MMDA-3b and MMDA-4.[2][1]

MMDA-5 was first described in the scientific literature by Shulgin and colleagues in 1969.[8][9][5] Subsequently, it was described in greater detail by Shulgin in PiHKAL in 1991.[1]

See also

References

  1. ^ a b c d e f g h i j k l 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. ^ a b c d e f g h 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. ^ a b c 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. ^ a b 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.
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