3-Methoxy-4-methylamphetamine

MMA
Clinical data
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A; US: Schedule I (isomer of PMMA);
Identifiers
	IUPAC name 1-(3-methoxy-4-methylphenyl)propan-2-amine;
CAS Number	24160-29-0 ;
PubChem CID	91253;
ChemSpider	82402 ;
UNII	BHS67KQE5Q;
ChEMBL	ChEMBL47696 ;
CompTox Dashboard (EPA)	DTXSID401007386 ;
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COc1cc(CC(N)C)ccc1C;
	InChI 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 ; Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N ;
	(what is this?) (verify)

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.^{[citation needed]}

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-HT_2A 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]

References

^ ^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): 1662–1668. doi:10.1021/jm00109a020. PMID 1674539.
^ de Zorzi C, Cavalli A (1974). "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)" [A new hallucinogen: MMA (p-methyl-m-methoxy amphetamine)]. Zacchia (in Italian). 49 (1): 58–68.
^ Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.
^ Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". Eur J Pharmacol. 200 (1): 9–16. doi:10.1016/0014-2999(91)90659-e. PMID 1685125.
^ ^a ^b Rudnick G, Wall SC (February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology. 43 (2): 271–276. doi:10.1016/S0026-895X(25)13609-2. PMID 8429828.
^ ^a ^b ^c Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5. 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.
^ Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug des Discov. 9 (3–4): 299–312. PMID 8400010.

[HoMcIsaacAn1970-1] 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.

[JohnsonFrescasOberlender1991-2] 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): 1662–1668. doi:10.1021/jm00109a020. PMID 1674539.

[3] Zorzi C, Cavalli A (1974). "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)" [A new hallucinogen: MMA (p-methyl-m-methoxy amphetamine)]. Zacchia (in Italian). 49 (1): 58–68.

[GlennonYoungHauck1985-4] Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.

[JohnsonConartyNichols1991-5] Johnson MP, Conarty PF, Nichols DE (July 1991). "[3H]monoamine releasing and uptake inhibition properties of 3,4-methylenedioxymethamphetamine and p-chloroamphetamine analogues". Eur J Pharmacol. 200 (1): 9–16. doi:10.1016/0014-2999(91)90659-e. PMID 1685125.

[RudnickWall1993-6] Rudnick G, Wall SC (February 1993). "Non-neurotoxic amphetamine derivatives release serotonin through serotonin transporters". Molecular Pharmacology. 43 (2): 271–276. doi:10.1016/S0026-895X(25)13609-2. PMID 8429828.

[ShulginShulgin1991-7] Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5. 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.

[NicholsMarona-LewickaHuang1993-8] Nichols DE, Marona-Lewicka D, Huang X, Johnson MP (1993). "Novel serotonergic agents". Drug des Discov. 9 (3–4): 299–312. PMID 8400010.

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3-Methoxy-4-methylamphetamine

See also

References

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