3-Methoxyamphetamine
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3-Methoxyamphetamine (3-MA), also known as meta-methoxyamphetamine (MMA), is a monoamine releasing agent (MRA) of the amphetamine family.[1][2][3] It is a positional isomer of para-methoxyamphetamine (PMA; 4-methoxyamphetamine).[4][5]
Effects
According to Alexander Shulgin, 3-MA showed no central or psychedelic effects in humans at a total dose of 50Script error: No such module "String".mg (25Script error: No such module "String".mg orally twice separated by 3Script error: No such module "String".hours).[4][5] However, sympathomimetic effects have occurred with the drug at an oral dose of 25Script error: No such module "String".mg in humans.[4][6]
Pharmacology
3-MA has similar effects in animal drug discrimination tests to PMA.[1] 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][2][8] 3-MA's EC50 values for induction of monoamine release are 58.0Script error: No such module "String".nM for norepinephrine and 103Script error: No such module "String".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] In another study, its affinities (Ki) for the serotonin 5-HT1 and 5-HT2 receptors were 2,660Script error: No such module "String".nM and 7,850Script error: No such module "String".nM, respectively.[11] 3-MA is also a weak agonist of the human trace amine-associated receptor 1 (TAAR1), with micromolar potency.[12]
3-MA produced hyperlocomotion, a psychostimulant-like effect, in rodents similarly to amphetamine and PMA.[13][14] It also produced hyperthermia and myoclonus, serotonin-associated effects, in rodents similarly to PMA.[13][14]
3-MA produces gepefrine (3-hydroxyamphetamine), a sympathomimetic agent, as one of its major metabolites.[15]
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.[16]
Analogues
The 2-aminoindane analogue of 3-MA is 5-methoxy-2-aminoindane (MEAI; 5-MeO-AI).[17]
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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- ↑ a b Script error: No such module "Citation/CS1".
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- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, "Acid Addition Salts of D-(+)-1-(3-Hydroxyphenyl)-2-Aminopropane and Their Manufacture and Use"Script error: No such module "Check for unknown parameters".
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- ↑ Schelling, J.L., Dufour, R.J., Jequier, E. (1974) Vasopressor effect of 3-methoxyamphetamine in man. Vortr. Symp. Meeting Date 1970, pp 175-183. "Like other amphetamines, 3-methoxyamphetamine (I) [17862-85-0] had a transient pressor effect on man. The minimal effective dose on oral administration was 25 mg. Differences between that dose and a placebo were significant in young normotensive subjects. The acute response of older patients with chronic hypotension to the same dose was unpredictable. Unlike other amphetamines, this drug did not produce any tachycardia. There was no sustained elevation of blood pressure when the drug was given twice daily for 3 days. The urinary excretion of catechol amines was unchanged."
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