3-Methoxyamphetamine

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Not to be confused with 3-Methoxy-4-methylamphetamine.
"3-MA" redirects here. For the musical group, see 3MA.
3-Methoxyamphetamine
File:3-methoxyamphetamine.svg
Clinical data
Other names3-MA; 3-MeO-A; meta-Methoxyamphetamine; MMA
Routes of
administration		Oral[1]
Drug classSerotonin–norepinephrine–dopamine releasing agent
ATC code
  • None
Identifiers
  • 1-(3-methoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
  • NC(C)CC1=CC=CC(OC)=C1
  • InChI=1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 checkY
  • Key:VEJWNIYARKAHFI-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

Effects

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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 EC50Tooltip half-maximal effective concentration 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] In another study, its affinities (Ki) for the serotonin 5-HT1 and 5-HT2 receptors were 2,660 nM and 7,850 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

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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

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The 2-aminoindane analogue of 3-MA is 5-methoxy-2-aminoindane (MEAI; 5-MeO-AI).[17]

See also

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References

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  4. ^ GB 1527479, "Acid Addition Salts of D-(+)-1-(3-Hydroxyphenyl)-2-Aminopropane and Their Manufacture and Use" 
  5. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ 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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