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3-Methoxyamphetamine
Stimulant drug of the amphetamine class From Wikipedia, the free encyclopedia
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3-Methoxyamphetamine (3-MA), also known as meta-methoxyamphetamine (MMA), is a monoamine releasing agent (MRA) of the amphetamine family.[2][3][4] It is a positional isomer of para-methoxyamphetamine (PMA; 4-methoxyamphetamine).[1][5]
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Effects
According to Alexander Shulgin, 3-MA showed no central or psychedelic effects in humans at a total dose of 50 mg (25 mg orally twice separated by 3 hours).[1][5] However, sympathomimetic effects have occurred with the drug at an oral dose of 25 mg in humans.[1][6]
Pharmacology
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3-MA has similar effects in animal drug discrimination tests to PMA.[2] However, it has a different balance of monoamine release, being a combined serotonin–norepinephrine–dopamine releasing agent (SNDRA) rather than a fairly selective serotonin releasing agent (SSRA) like PMA.[7][3][8] 3-MA's EC50 values for induction of monoamine release are 58.0 nM for norepinephrine and 103 nM for dopamine in rat brain synaptosomes, whereas the value for serotonin was not reported.[7]
The drug has shown relatively low affinity for serotonin receptors in the rat stomach fundus strip, intermediate between amphetamine and amphetamine psychedelics like DOM and DOB.[9][10] 3-MA is also a weak agonist of the human trace amine-associated receptor 1 (TAAR1), with micromolar potency.[11]
3-MA produced hyperlocomotion, a psychostimulant-like effect, in rodents similarly to amphetamine and PMA.[12][13] It also produced hyperthermia and myoclonus, serotonin-associated effects, in rodents similarly to PMA.[12][13]
3-MA produces gepefrine (3-hydroxyamphetamine), a sympathomimetic agent, as one of its major metabolites.[14]
Recreational use
3-MA has appeared on the illicit market as a designer drug alternative to MDMA similarly PMA, although far more rarely than its infamous positional isomer.[15]
Analogues
The 2-aminoindane analogue of 3-MA is 5-methoxy-2-aminoindane (MEAI; 5-MeO-AI).[16]
See also
- Substituted methoxyphenethylamine
- 2-Methoxyamphetamine (OMA)
- 3-Methylamphetamine (3-MA)
- 3-Fluoroamphetamine (3-FA)
- 3-Trifluoromethylamphetamine (Norfenfluramine)
- 3-Methoxy-4-methylamphetamine (MMA)
- 3-Methoxymethamphetamine (MMMA)
- 4-Ethoxyamphetamine (4-ETA)
- 3,4-Dimethoxyamphetamine (DMA)
References
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