3-Methoxy-4-methylamphetamine

3-Methoxy-4-methylamphetamine
3-Methoxy-4-methylamphetamine
Systematic (IUPAC) name
1-(3-methoxy-4-methylphenyl)propan-2-amine
Clinical data
Pregnancy cat.  ?
Legal status Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes Oral
Identifiers
CAS number 87179-33-7
ATC code None
PubChem CID 91253
ChemSpider 82402 YesY
ChEMBL CHEMBL47696 YesY
Chemical data
Formula C11H17NO 
Mol. mass 179.258 g/mol
SMILES eMolecules & PubChem
 YesY(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.[4]

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]

According to anecdotal reports, MMA is active in humans at doses of 20-60 mg and possesses a duration of approximately 12-16 hours.[4] It is said to produce empathy and mild 2C-like psychedelic effects, and although it is mood-lifting, it is not euphoric like MDMA and is more antidepressant-like in comparison.[4] At higher doses, such as 140 mg, the effects are much more psychedelic (comparable to DOM) but can be dysphoric and very long-lived.[5]

See also

  • 3-Methoxyamphetamine (3-MeOA)
  • 3-Methoxymethamphetamine (MMMA)
  • 4-Methylamphetamine (4-MA)
  • 4-Methylmethamphetamine (4-MMA)
  • 4-Methylmethcathinone (4-MMC)

References

  1. ^ a b Ho BT, McIsaac WM, An R, et al. (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, Zacchia. 1974;10:3.
  4. ^ a b c "Bluelight Forums - MMA - 3-MeO-4-Me-Amphetamine". http://www.bluelight.ru/vb/showthread.php?t=362771. 
  5. ^ Ann Shulgin; Alexander Shulgin (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5. http://www.erowid.org/library/books_online/pihkal/pihkal123.shtml. 
v · d · eEntactogens
Aminoindanes
5-IAI • ETAI • TAI
Aminotetralins
6-CAT
Phenethylamines
(and amphetamines,
cathinones, etc)
4-CAB • 4-FA • 4-FMA • 4-MTA • 4-FPP • 5-APDB • 6-APDB • Ariadne • BDB • Brephedrone • Eutylone • Flephedrone • IAP • IMP • Metaescaline • Mephedrone • Methedrone • MMA • NAP • Norfenfluramine • Pentylone • PMA • PMEA • PMMA • TAP
MDxx
2-Methyl-MDA • 5-Methyl-MDA • 6-Methyl-MDA • bk-MBDB (butylone) • bk-MDEA (ethylone) • bk-MDMA (methylone) • DMMDA • DMMDA-2 • EBDB • EBDP • EDMA • MDAI • MDMAI • MMAI • MDAT • MDMAT • MDA • MDDM • MDEA • MDIP • MDMA • MDMOH • MDMP • MDMPEA • MDOH • MDPEA • MDPH • MDPR • MMDPEA (Lophophine) • MBDB • MBDP • MMDA • MMDA-2 • MMDMA
Tryptamines
4-Methyl-αET • αET
v · d · eHallucinogens
Psychedelics
5-HT2AR agonists
Dissociatives
NMDAR antagonists
Deliriants
mAChR antagonists
Miscellaneous
Cannabinoids
CB1R agonists
Others
v · d · ePhenethylamines
Phenethylamines
Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-F • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2
Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA)
Entactogens: Lophophine • MDPEA • MDMPEA
Others: BOH • DMPEA
Amphetamines
Phenylisopropylamines
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: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Norfenfluramine • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine
Entactogens: 5-APDB • 6-APB • 6-APDB • EDA • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP
Others: Amiflamine • DFMDA • D-Deprenyl • L-Deprenyl (Selegiline)
Phentermines
Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine
Entactogens: MDPH • MDMPH
Cathinones
Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone
Entactogens: Ethylone • Methylone
Phenylisobutylamines
Entactogens: 4-CAB • 4-MAB • Ariadne (α-Et-DOM) • BDB (J) • Butylone (bk-MBDB) • EBDB (Ethyl-J) • Eutylone (bk-EBDB) • MBDB (Methyl-J)
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP • α-PPP • α-PVP • MDPBP • MDPPP • MDPV • MOPPP • MPBP • MPHP • MPPP • Naphyrone • PEP • Prolintane • Pyrovalerone
Catecholamines
(and relatives..)
6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine
Miscellaneous
Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol

Wikimedia Foundation. 2010.

Игры ⚽ Поможем сделать НИР

Look at other dictionaries:

  • 2,5-Dimethoxy-4-methylamphetamine — 2,5 Dimethoxy 4 methylamphetamine …   Wikipedia

  • Substituted amphetamine — Optical isomers of amphetamine D amphetamine …   Wikipedia

  • Substituted methylenedioxyphenethylamines — Methylenedioxyphenethylamine (MDPEA) Substituted methylenedioxy phenethylamines (MDxx) make up a large chemical class of derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelics, and/or …   Wikipedia

  • Methoxyphenamine — Systematic (IUPAC) name 1 (2 methoxyphenyl) N methylpropan 2 amine Clinical data AHFS/Drugs.com …   Wikipedia

  • para-Methoxyamphetamine — Systematic (IUPAC) name 1 (4 methoxyphenyl)propan 2 amine Clinical data Pregnancy cat.  ? …   Wikipedia

  • Releasing agent — Amphetamine, the prototypical releasing agent, which acts on norepinephrine and dopamine. A releasing agent (RA), or simply releaser, is a drug that induces the release of a neurotransmitter from the presynaptic neuron into the synapse, leading… …   Wikipedia

  • Norepinephrine releasing agent — Norepinephrine A norepinephrine releasing agent (NRA) is a type of drug which induces the release of norepinephrine and epinephrine from the pre synaptic neuron into the synapse. This in turn leads to increased extracellular concentrations of… …   Wikipedia

  • MDMA — Systematic (IUPAC) name (RS) 1 (benzo[d][1,3]dioxol 5 …   Wikipedia

  • DOx — 2,5 Dimethoxyamphetamine (2,5 DMA), the base structure of the DOx family. DOx is a term used to refer to a chemical class of substituted amphetamine derivatives featuring methoxy groups at the 2 and 5 positions of the phenyl ring, and a… …   Wikipedia

  • Arylcyclohexylamine — Phencyclidine, the prototypal arylcyclohexylamine derivative. Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs. Contents …   Wikipedia

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”