Chemistry:3-Methoxy-4-methylamphetamine

From HandWiki

3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes.[1][2] It was first synthesized in 1970[1] and was encountered as a street drug in Italy in the same decade.[3] MMA was largely forgotten until being reassayed by David E. Nichols as a non-neurotoxic MDMA analogue in 1991,[2] 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.[2] However, in another study, MMA fully substituted for dextroamphetamine in such tests.[4] Additionally, it has been shown to be a potent and highly selective serotonin releasing agent (SSRA) and does not produce serotonergic neurotoxicity in rodents.[5][2][6] These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and serotonin 5-HT2A receptor agonist.[2]

In humans, MMA has been reported to be hallucinogenic, "quite dypshoric", and long-lasting.[7] The active doses have been reported to be 40 to 60 mg.[7] Capsules containing 140 mg have been encountered as a designer drug in Italy in the 1980s.[7]

The 2-aminoindane analogue of MMA is 5-methoxy-6-methyl-2-aminoindane (MMAI).[8][6]

See also

References

  1. ↑ 1.0 1.1 "Analogs of alpha-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs". Journal of Medicinal Chemistry 13 (1): 26–30. January 1970. doi:10.1021/jm00295a007. PMID 5412110. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 "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 34 (5): 1662–1668. May 1991. doi:10.1021/jm00109a020. PMID 1674539. 
  3. ↑ "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)" (in Italian). Zacchia 49 (1): 58–68. 1974. 
  4. ↑ "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav 22 (5): 723–729. May 1985. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. 
  5. ↑ "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". Eur J Pharmacol 200 (1): 9–16. July 1991. doi:10.1016/0014-2999(91)90659-e. PMID 1685125. 
  6. ↑ 6.0 6.1 "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology 43 (2): 271–276. February 1993. doi:10.1016/S0026-895X(25)13609-2. PMID 8429828. 
  7. ↑ 7.0 7.1 7.2 Pihkal: A Chemical Love Story. Transform Press. 1991. ISBN 0-9630096-0-5. http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml. "Some years ago a report appeared in the forensic literature of Italy, of the seizure of a small semi-transparent capsule containing 141 milligrams of a white powder that was stated to be a new hallucinogenic drug. This was shown to contain an analogue of DOM, 3-methoxy-4-methylamphetamine, or MMA. The Italian authorities made no mention of the net weight contained in each dosage unit, but it has been found that the active level of MMA in man is in the area of 40-60 milligrams. The compound can apparently be quite dysphoric, and long lived." 
  8. ↑ "Novel serotonergic agents". Drug des Discov 9 (3–4): 299–312. 1993. PMID 8400010. https://bitnest.netfirms.com/external/DrugDes.Disc/9.299. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:3-Methoxy-4-methylamphetamine&oldid=4309796"