2-Methoxyamphetamine

2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine family. It is substantially weaker in inhibiting the reuptake of and inducing the release of the monoamine neurotransmitters compared to related agents such as amphetamine, MMA, and PMA,^[1] and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine.^[2] The drug also shows relatively weak affinity for serotonin receptors, including the serotonin 5-HT₁ and 5-HT₂ receptors (K_i = 3,500 nM and 8,130 nM, respectively).^[3] 2-MA fully substitutes for dextroamphetamine in rodent drug discrimination tests.^[4]

2-Methoxyamphetamine

Clinical data
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 1-(2-methoxyphenyl)propan-2-amine
CAS Number	15402-84-3 N
PubChem CID	159755
ChemSpider	140465 Y
ChEMBL	ChEMBL16451 Y
CompTox Dashboard (EPA)	DTXSID80934899
Chemical and physical data
Formula	C10H15NO
Molar mass	165.236 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1ccccc1CC(N)C)C
InChI InChI=1S/C10H15NO/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3 Y Key:VBAHFEPKESUPDE-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

See also

• Substituted methoxyphenethylamine
• Methoxyphenamine
• 3-Methoxyamphetamine (MMA)
• 4-Methoxyamphetamine (PMA)