Chemistry:MMDA-5

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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. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 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.  "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. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 "Psychotomimetic Drugs: Structure-Activity Relationships". Stimulants. Boston, MA: Springer US. 1978. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6. https://bitnest.netfirms.com/external/10.1007/978-1-4757-0510-2_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. ↑ 3.0 3.1 3.2 "Basic Pharmacology and Effects". Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. 2003. pp. 67–137. ISBN 978-0-12-433951-4. https://bibliography.maps.org/resources/download/12634. "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". https://isomerdesign.com/pihkal/notebooks/transcripts/p1/p1.166.pdf. 
  5. ↑ 5.0 5.1 "Psychotomimetic Agents". Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. 4. Academic Press. 1976. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9. "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. ↑ "Hallucinogens". Burger's Medicinal Chemistry. 3 (4 ed.). New York: Wiley. 1980. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627. https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5. 
  7. ↑ "Chemistry of Psychotomimetics". Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. 55. Berlin: Springer Berlin Heidelberg. 1982. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916. https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1. 
  8. ↑ "Structure--activity relationships of one-ring psychotomimetics". Nature 221 (5180): 537–541. February 1969. doi:10.1038/221537a0. PMID 5789297. Bibcode: 1969Natur.221..537S. https://bibliography.maps.org/resources/download/11267. 
  9. ↑ "Mescaline: the chemistry and pharmacology of its analogs". Lloydia 36 (1): 46–58. March 1973. PMID 4576313. https://bibliography.maps.org/resources/download/9043. "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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