Chemistry:3-Methoxy-4-methylamphetamine

3-Methoxy-4-methylamphetamine
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 ;
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 ;
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Short description: Entactogen and psychedelic drug of the phenethylamine and amphetamine classes

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).

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-HT_2A receptor agonist.^[2]

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

References

↑ ^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.
↑ ^2.0 ^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.
↑ "Un nuovo allucinogeno: la MMA (p-metil-m-metossi anfetamina)" (in Italian). Zacchia 49 (1): 58–68. 1974.
↑ Pihkal: A Chemical Love Story. Transform Press. 1991. ISBN 0-9630096-0-5. http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml.

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[pmid5412110-1] 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.

[pmid1674539-2] 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.

[isbn0-9630096-0-5-4] Pihkal: A Chemical Love Story. Transform Press. 1991. ISBN 0-9630096-0-5. http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml.

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v t e Empathogens/entactogens
Phenylalkyl- amines (other than cathinones)	Unfused benzene ring: 3-CMA 4-CAB 4-FA 4-MA 4-MMA 4-FMA 4-MTA 4,4'-DMAR Ariadne Metaescaline MMA PMA PMEA PMMA mMMA Benzodioxine: EDMA Benzodioxoles: Phenethylamine: { Lophophine } Amphetamines: { 2-Methyl-MDA 2,3-MDA 3,4-MDA (tenamfetamine) 5-Methyl-MDA 6-Methyl-MDA DiFMDA DMMDA DMMDA-2 EIDA MDEA MDMA (midomafetamine) MDMOH MDOH MMDA MMDA-2 MMDMA } 1-Phenylbutan-2-amines: { BDB EBDB MBDB } Phentermines: { MDMP MDPH } Benzofurans and dihydrobenzofurans: 5-APB 5-APDB 5-EAPB 5-MAPB 5-MAPDB 5-MBPB 6-APB 6-APDB 6-EAPB 6-MAPB 6-MAPDB IBF5MAP Indanes: 5-APDI 5-MAPDI Indoles: 5-IT 6-API Naphthalenes: Methamnetamine Naphthylaminopropane Tetralin: 6-APT
Cyclized phenyl- alkylamines	Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI MEAI NM-2-AI TAI Aminotetralins: 6-CAT MDAT MDMAT
Cathinones	3-MMC 4-EMC Brephedrone Butylone Ethylone Eutylone Flephedrone Mephedrone Methedrone Methylone TH-PVP
Tryptamines	4-Methyl-αET αET αMT
Chemical classes	Substituted amphetamine Sub. benzofuran Sub. cathinone Sub. MDPEA Sub. PEA Sub. tryptamine

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-BZ 3C-E 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L -Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA Phenpromethamine PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D -Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D -DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L -DOPA (Levodopa) L -DOPS (Droxidopa) L -Phenylalanine L -Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101

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Chemistry:3-Methoxy-4-methylamphetamine

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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^Y
PubChem CID	91253
ChemSpider	82402^Y
UNII	BHS67KQE5Q
ChEMBL	ChEMBL47696^Y
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^Y Key:XDXMRSBXBOXSQW-UHFFFAOYSA-N^Y
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Chemistry:3-Methoxy-4-methylamphetamine

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