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ChemSpider 82402
PubChem 91253
Wikidata Q2813117
Wikipedia 3-Methoxy-4-methylamphetamine
Rhodium Synthesis of 3-methoxy-4-methyl-amphetamine (MMA) (XIII)
Rhodium Synthesis of 4-methyl-3-methoxy-amphetamine (MMA)

Shulgin Index #96 3,4-MMA · Table 4Page 328Row 3

Phenethylamine: Von der Strucktur zur Funktion MMA: 7.5 (24) 549, 554

Johnson, MP; Frescas, SP; Oberlender, R; Nichols, DE. 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). J. Med. Chem., 1 May 1991, 34 (5), 1662–1668. 975 kB. https://doi.org/10.1021/jm00109a020 #6 NMR

Aldous, FAB; Barrass, BC; Brewster, K; Buxton, DA; Green, DM; Pinder, RM; Rich, P; Skeels, PM; Tutt, KJ. Structure-activity relationships in psychotomimetic phenylalkylamines. J. Med. Chem., 1 Oct 1974, 17 (10), 1100–1111. 1.2 MB. https://doi.org/10.1021/jm00256a016 #11 other

Johnson, MP; Conarty, PF; Nichols, DE. [³H]Monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues. Eur. J. Pharmacol., 23 Jul 1991, 200 (1), 9–16. 1.1 MB. https://doi.org/10.1016/0014-2999(91)90659-E #MMA

Ho, B; McIsaac, WM; An, R; Tansey, LW; Walker, KE; Englert, LF; Noel, MB. Analogs of α-methylphenethylamine (amphetamine). I. Synthesis and pharmacological activity of some methoxy and/or methyl analogs. J. Med. Chem., 1 Jan 1970, 13 (1), 26–30. 601 kB. https://doi.org/10.1021/jm00295a007 #4

Brimblecombe, RW; Pinder, RM. Hallucinogenic agents, Wright-Scientechnica, Bristol, UK, 1 Jan 1975. 46.2 MB. #3.36

Nichols, DE. Medicinal chemistry and structure-activity relationships. In Amphetamine and its Analogs; Cho, AK; Segal, DS, Eds., Academic Press, San Diego, CA, 1 Jan 1994; pp 3–41. 8.1 MB. #20

Monte, AP; Marona-Lewicka, D; Cozzi, NV; Nichols, DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. J. Med. Chem., 1 Nov 1993, 36 (23), 3700–3706. 1.0 MB. https://doi.org/10.1021/jm00075a027 #2 MS,NMR

Marcher-Rørsted, E; Halberstadt, AL; Klein, AK; Chatha, M; Jademyr, S; Jensen, AA; Kristensen, JL. Investigation of the 2,5-dimethoxy motif in phenethylamine serotonin 2A receptor agonists. ACS Chem. Neurosci., 26 Mar 2020, 11 (9), 1238-1244. 3.8 MB. https://doi.org/10.1021/acschemneuro.0c00129 #15 LC,MS,NMR

Shulgin, AT. Psychotomimetic drugs: structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 243–333. 2.6 MB. https://doi.org/10.1007/978-1-4757-0510-2_6 #71 Rhodium.

Gupta, SP; Singh, P; Bindal, MC. QSAR studies on hallucinogens. Chem. Rev., 1 Dec 1983, 83 (6), 633–649. 2.8 MB. https://doi.org/10.1021/cr00058a003 #62

Nichols, DE; Marona-Lewicka, D; Huang, X; Johnson, MP. Novel serotonergic agents. Drug Des. Discovery, 1 Feb 1993, 9 (3–4), 299–312. 4.7 MB. #MMA

4-MMA · 4-MeO-MA · 4-Methoxymethamphetamine · DOONE · METHYL-MA · PMMA

2-MMA · 2-MeO-MA · 2-Methoxymethamphetamine · MPA · OMMA

Methylephedrine · β-Hydroxy-N,N-dimethylamphetamine

3,5-Me-4-MPEA · 4-Methoxy-3,5-dimethylphenethylamine

3-MMA · 3-MeO-MA · 3-Methoxymethamphetamine · MMMA

4-EA · 4-Ethoxyamphetamine

4-Hydroxy-N,N,N-trimethylphenethylamine⁺ · Candicine

2,4-MMA · 2-Methoxy-4-methylamphetamine · 5H-DOM

2406

homo-PMA

N,N-Dimethyl-2-methoxyphenethylamine · N,N-Me-2-MPEA

β,N-Dimethyl-2-methoxyphenethylamine · β,N-Me-2-MPEA

4C-2-MPEA · α-Ethyl-2-methoxyphenethylamine

N-Me-2-EPEA · N-Methyl-2-ethoxyphenethylamine

2-EA · 2-Ethoxyamphetamine

N,N,N-Trimethyl-3-hydroxyphenethylamine⁺ · Leptodactyline

N-Et-3-HA · N-Ethyl-3-hydroxyamphetamine

N,N-Dimethyl-3-methoxyphenethylamine · N,N-Me-3-MPEA

N-Et-3-MPEA · N-Ethyl-3-methoxyphenethylamine

4C-3-MPEA · α-Ethyl-3-methoxyphenethylamine

N-Me-3-EPEA · N-Methyl-3-ethoxyphenethylamine

3-EA · 3-Ethoxyamphetamine

N,N-Dimethyl-4-hydroxyphenethylamine · PHMMA

N-Ethyl-4-hydroxyamphetamine · PHEA

4-Methoxy-N,N-dimethylphenethylamine · N,N-Me-4-MPEA

β,N-Dimethyl-4-methoxyphenethylamine · β,N-Me-4-MPEA

N,N-Dimethyl-4-methoxyphenethylamine · α,α-Me-PMPEA

α-Et-MPEA · α-Ethyl-4-methoxyphenethylamine

N-Me-4-EPEA · N-Methyl-4-ethoxyphenethylamine

4-PPEA · 4-Propylphenethylamine

2,3-HMeMMPEA · 2-Hydroxy-3-methyl-N,N-dimethylphenethylamine

2,3-HMeMA · 2-Hydroxy-3-methylmethamphetamine

2,3-MMeA · 2-Methoxy-3-methylamphetamine

β-HO-3,4,N-MePEA · β-Hydroxy-3,4,N-trimethylphenethylamine

3,5-Me-PHA · 4-Hydroxy-3,5-dimethylamphetamine

2,6-Me-MPEA · 4-Methoxy-2,6-dimethylphenethylamine

2-Methoxy-4,6-dimethylphenethylamine · 4,6-Me-2-MPEA

5,2-MMeA · 5-Methoxy-2-methylamphetamine

N,N-Dimethylamphetamine N-oxide · DMA N-oxide

N-(2-Hydroxyethyl)amphetamine

N-MeO-PMeA · N-Methoxy-4-methylamphetamine

Mexiletine

4-MeO-2-MeA · 4-Methoxy-2-methylamphetamine

5,2-EtMPEA · 5-Ethyl-2-methoxyphenethylamine

HM-α-EPEA · α-Et-3,4-HMePEA · α-Ethyl-3-hydroxy-4-methylphenethylamine

3,4-HEtA · 3-Hydroxy-4-ethylamphetamine

4,3-MMeA · 4-Methoxy-3-methylamphetamine

10527

4-Methylephedrine · β-Hydroxy-4-methylmethamphetamine

β-Me-2H-2C-D

5H-2C-G

Methylpseudoephedrine · β-HO-N,N-Me-A · β-Hydroxy-N,N-dimethylamphetamine

α-Methylephedrine

β-Methoxy-N,N-dimethylphenethylamine

p3-396: MMA