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Wikipedia

3-Methoxy-4-methylamphetamine

January 17, 2023

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 (decade).

3-Methoxy-4-methylamphetamine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(3-methoxy-4-methylphenyl)propan-2-amine
CAS Number
  • 24160-29-0 Y
PubChem CID
  • 91253
ChemSpider
  • 82402 Y
UNII
  • BHS67KQE5Q
ChEMBL
  • ChEMBL47696 Y
CompTox Dashboard (EPA)
  • DTXSID401007386
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
  • Interactive image
  • COc1cc(CC(N)C)ccc1C
  • InChI=1S/C11H17NO/c1-8-4-5-10(6-9(2)12)7-11(8)13-3/h4-5,7,9H,6,12H2,1-3H3 Y
  • Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

In animal studies, MMA fully substitutes for MDMA and MBDB, partially substitutes for LSD, and does not substitute for amphetamine.[2] Additionally, it has been shown to potently inhibit the reuptake of serotonin and does not produce serotonergic neurotoxicity in rodents.[2] These data appear to confer a profile of MMA as a selective serotonin releasing agent (SSRA) and 5-HT2A receptor agonist.[2]

At high doses, such as 120 mg, the effects are psychedelic (comparable to DOM).[4]

See also

References

  1. ^ a b Ho BT, McIsaac WM, An R, Tansey LW, Walker KE, Englert LF, Noel MB (January 1970). "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. doi:10.1021/jm00295a007. PMID 5412110.
  2. ^ a b c d e Johnson MP, Frescas SP, Oberlender R, Nichols DE (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. 34 (5): 1662–8. doi:10.1021/jm00109a020. PMID 1674539.
  3. ^ de Zorzi C, Cavalli A, Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina) Zacchia. 1974;49 (1) p.58-68
  4. ^ Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.

January 17, 2023
methoxy, methylamphetamine, entactogen, psychedelic, drug, phenethylamine, amphetamine, classes, first, synthesized, 1970, encountered, street, drug, italy, same, decade, largely, forgotten, until, being, reassayed, david, nichols, neurotoxic, mdma, analogue, . 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 decade 3 Methoxy 4 methylamphetamineClinical dataRoutes ofadministrationOralATC codenoneLegal statusLegal statusDE NpSG Industrial and scientific use only UK Class A US Schedule I isomer of PMMA IdentifiersIUPAC name 1 3 methoxy 4 methylphenyl propan 2 amineCAS Number24160 29 0 YPubChem CID91253ChemSpider82402 YUNIIBHS67KQE5QChEMBLChEMBL47696 YCompTox Dashboard EPA DTXSID401007386Chemical and physical dataFormulaC 11H 17N OMolar mass179 263 g mol 13D model JSmol Interactive imageSMILES COc1cc CC N C ccc1CInChI InChI 1S C11H17NO c1 8 4 5 10 6 9 2 12 7 11 8 13 3 h4 5 7 9H 6 12H2 1 3H3 YKey XDXMRSBXBOXSQW UHFFFAOYSA N Y N Y what is this verify In animal studies MMA fully substitutes for MDMA and MBDB partially substitutes for LSD and does not substitute for amphetamine 2 Additionally it has been shown to potently inhibit the reuptake of serotonin and does not produce serotonergic neurotoxicity in rodents 2 These data appear to confer a profile of MMA as a selective serotonin releasing agent SSRA and 5 HT2A receptor agonist 2 At high doses such as 120 mg the effects are psychedelic comparable to DOM 4 See also Edit3 Methoxyamphetamine 3 MeOA 3 Methoxymethamphetamine MMMA 4 Methylamphetamine 4 MA 4 Methylmethamphetamine 4 MMA 4 Methylmethcathinone 4 MMC 4 Cl 3 MMCReferences Edit a b Ho BT McIsaac WM An R Tansey LW Walker KE Englert LF Noel MB January 1970 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 doi 10 1021 jm00295a007 PMID 5412110 a b c d e Johnson MP Frescas SP Oberlender R Nichols DE 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 34 5 1662 8 doi 10 1021 jm00109a020 PMID 1674539 de Zorzi C Cavalli A Un nuovo allucinogeno la MMA p metil m metossi anfetamina Zacchia 1974 49 1 p 58 68 Shulgin A Shulgin A 1991 Pihkal A Chemical Love Story Transform Press ISBN 0 9630096 0 5 Retrieved from https en wikipedia org w index php title 3 Methoxy 4 methylamphetamine amp oldid 1130147027, wikipedia, wiki, book, books, library,

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