3-Methoxyamphetamine

Not to be confused with 3-Methoxy-4-methylamphetamine.

"3-MA" redirects here. For the musical group, see 3MA.

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]

3-Methoxyamphetamine

Clinical data
Other names	3-MA; 3-MeO-A; meta-Methoxyamphetamine; MMA
Routes of administration	Oral[1]
Drug class	Serotonin–norepinephrine–dopamine releasing agent
ATC code	None
Identifiers
IUPAC name 1-(3-methoxyphenyl)propan-2-amine
CAS Number	17862-85-0 Y
PubChem CID	152234
ChemSpider	134180 Y
UNII	C2B7C98LY8
ChEMBL	ChEMBL16247 Y
CompTox Dashboard (EPA)	DTXSID00939104
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image
SMILES NC(C)CC1=CC=CC(OC)=C1
InChI InChI=1S/C10H15NO/c1-8(11)6-9-4-3-5-10(7-9)12-2/h3-5,7-8H,6,11H2,1-2H3 Y Key:VEJWNIYARKAHFI-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

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] 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)