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3-Methoxy-4-methylamphetamine

Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

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3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade. MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991, and has subsequently been sold as a designer drug on the internet since the late 2000s.

In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine in rodent drug discrimination tests. However, in another study, MMA fully substituted for dextroamphetamine in such tests. Additionally, it has been shown to be a potent and highly selective serotonin releasing agent (SSRA) and does not produce serotonergic neurotoxicity in rodents. These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and serotonin 5-HT2A receptor agonist.

In humans, MMA has been reported to be hallucinogenic, "quite dypshoric", and long-lasting. The active doses have been reported to be 40 to 60mg. Capsules containing 140mg have been encountered as a designer drug in Italy in the 1980s.

The 2-aminoindane analogue of MMA is 5-methoxy-6-methyl-2-aminoindane (MMAI).

References

References

  1. (January 1970). "Analogs of alpha-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs". Journal of Medicinal Chemistry.
  2. (May 1991). "Synthesis and pharmacological examination of 1-(3-methoxy-4-methylphenyl)-2-aminopropane and 5-methoxy-6-methyl-2-aminoindan: similarities to 3,4-(methylenedioxy)methamphetamine (MDMA)". Journal of Medicinal Chemistry.
  3. (1974). "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)". Zacchia.
  4. (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav.
  5. (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". Eur J Pharmacol.
  6. (1991). "Pihkal: A Chemical Love Story". Transform Press.
  7. (1993). "Novel serotonergic agents". Drug des Discov.
  8. (February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology.
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david-e.-nichols designer-drugs entactogens methoxyphenethylamines phenol-ethers psychedelic-phenethylamines serotonin-receptor-agonists serotonin-releasing-agents substances-discovered-in-the-1970s substituted-amphetamines
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