Chemistry:3-Methoxyamphetamine

From HandWiki
Short description: Stimulant drug of the amphetamine class
3-Methoxyamphetamine
3-Methoxyamphetamine.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
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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

References

  1. "Acid Addition Salts of D-(+)-1-(3-Hydroxyphenyl)-2-Aminopropane and Their Manufacture and Use" GB patent 1527479
  2. "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior 22 (5): 723–9. May 1985. doi:10.1016/0091-3057(85)90520-9. PMID 3839309. 
  3. "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. May 1976. PMID 1271280. 
  4. "Pharmacological evidence for the central serotonergic effects of monomethoxyamphetamines". The Journal of Pharmacology and Experimental Therapeutics 197 (2): 272–9. May 1976. PMID 946817. 
  5. "A re-examination of the mono-methoxy positional ring isomers of amphetamine, methamphetamine and phenyl-2-propanone". Forensic Science International 119 (2): 168–94. June 2001. doi:10.1016/S0379-0738(00)00425-4. PMID 11376983. 
  6. "The metabolism of 3-methoxyamphetamine in dog, monkey and man". Xenobiotica; the Fate of Foreign Compounds in Biological Systems 11 (2): 137–46. February 1981. doi:10.3109/00498258109045284. PMID 6894510.