2-Methoxyamphetamine

2-Methoxyamphetamine
Clinical data
Other names	2-MA; ortho-Methoxyamphetamine; OMA
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name 1-(2-methoxyphenyl)propan-2-amine;
CAS Number	15402-84-3 ;
PubChem CID	159755;
ChemSpider	140465 ;
UNII	8NC8ZCZ6JE;
ChEMBL	ChEMBL16451 ;
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 ; Key:VBAHFEPKESUPDE-UHFFFAOYSA-N ;
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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]

References

↑ Tseng LF, Menon MK, Loh HH (May 1976). "Comparative actions of monomethoxyamphetamines on the release and uptake of biogenic amines in brain tissue". The Journal of Pharmacology and Experimental Therapeutics. 197 (2): 263–271. PMID 1271280.
↑ Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
↑ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". J Med Chem. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
↑ Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacol Biochem Behav. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.

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