2-Methoxyamphetamine

2-Methoxyamphetamine
Clinical data
Other names2-MA; ortho-Methoxyamphetamine; o-Methoxyamphetamine; OMA
Routes of
administration		Oral
ATC code
  • None
Identifiers
  • 1-(2-methoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H15NO
Molar mass165.236 g·mol−1
3D model (JSmol)
  • O(c1ccccc1CC(N)C)C
  • InChI=1S/C10H15NO/c1-8(11)7-9-5-3-4-6-10(9)12-2/h3-6,8H,7,11H2,1-2H3 checkY
  • Key:VBAHFEPKESUPDE-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

2-Methoxyamphetamine (2-MA), also known as ortho-methoxyamphetamine (OMA), is a drug of the amphetamine family. The properties and effects of 2-MA in humans are not known. 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, and may instead act as a β-adrenergic receptor agonist similarly to its N-methylated analogue methoxyphenamine. The drug also shows relatively weak affinity for serotonin receptors, including the serotonin 5-HT1 and 5-HT2 receptors (Ki = 3,500 nM and 8,130 nM, respectively). 2-MA fully substitutes for dextroamphetamine in rodent drug discrimination tests. The chemical synthesis of 2-MA has been described.

See also

References

  1. 1 2 3 Shulgin A, Shulgin A (1991). Pihkal: A Chemical Love Story. Transform Press. ISBN 0-9630096-0-5.
  2. ↑ 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.
  3. ↑ Glennon RA (January 1987). "Central serotonin receptors as targets for drug research". Journal of Medicinal Chemistry. 30 (1): 1–12. doi:10.1021/jm00384a001. PMID 3543362. Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
  4. ↑ Glennon RA, Young R, Hauck AE (May 1985). "Structure-activity studies on methoxy-substituted phenylisopropylamines using drug discrimination methodology". Pharmacology, Biochemistry, and Behavior. 22 (5): 723–729. doi:10.1016/0091-3057(85)90520-9. PMID 3839309.
  5. ↑ Shulgin A, Manning T, Daley PF (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0.