3-Methoxyamphetamine

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3-Methoxyamphetamine
3-Methoxyamphetamine.png
Systematic (IUPAC) name
1-(3-methoxyphenyl)propan-2-amine
Clinical data
Legal status
  •  ?
Routes Oral
Identifiers
CAS number 17862-85-0 N
ATC code None
PubChem CID 152234
ChemSpider 134180 YesY
ChEMBL CHEMBL16247 YesY
Chemical data
Formula C10H15NO 
Mol. mass 165.232 g/mol
 N (what is this?)  (verify)

meta-Methoxyamphetamine[1] (MMA), also known as 3-methoxyamphetamine (3-MA), is a stimulant drug from the amphetamine family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA),[2] although with a slightly different ratio of monoamine release, being a combined serotonin, dopamine, and norepinephrine releasing agent rather than a fairly selective serotonin releaser like PMA.[3][4] 3-Methoxyamphetamine has similarly appeared on the illicit market as a designer drug alternative to MDMA, although far more rarely than its infamous positional isomer.[5] It produces gepefrine, a cardiac stimulant, as one of its major metabolites.[6]

See also[edit]

References[edit]

  1. ^ GB Patent 1527479 - ACID ADDITION SALTS OF D-(+)-1-(3-HYDROXYPHENYL)-2-AMINOPROPANE AND THEIR MANUFACTURE AND USE
  2. ^ Glennon, RA; Young, R; Hauck, AE (1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior 22 (5): 723–9. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. 
  3. ^ Tseng, LF; Menon, MK; Loh, HH (1976). "Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue". The Journal of Pharmacology and Experimental Therapeutics 197 (2): 263–71. PMID 1271280. 
  4. ^ Menon, MK; Tseng, LF; Loh, HH (1976). "Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines". The Journal of Pharmacology and Experimental Therapeutics 197 (2): 272–9. PMID 946817. 
  5. ^ Dal Cason, TA (2001). "A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone". Forensic Science International 119 (2): 168–94. doi:10.1016/S0379-0738(00)00425-4. PMID 11376983. 
  6. ^ Midha, KK; Cooper, JK; Bailey, K; Hubbard, JW (1981). "The metabolism of 3-methoxyamphetamine in dog, monkey and man". Xenobiotica 11 (2): 137–46. doi:10.3109/00498258109045284. PMID 6894510.