Methoxyphenamine (trade names ASMI, Euspirol, Orthoxine, Ortodrinex, Proasma), also known as 2-methoxy-N-methylamphetamine (OMMA), is a β-adrenergic receptor agonist of the amphetamine class used as a bronchodilator.
Methoxyphenamine was first synthesized at the Upjohn company by Woodruff and co-workers. A later synthesis by Heinzelman, from the same company, corrects the m.p. given for methoxyphenamine hydrochloride in the earlier paper, and describes an improved synthetic procedure, as well as resolution of the racemic methoxyphenamine.
- 2-Methoxyamphetamine (OMA)
- 3-Methoxy-N-methylamphetamine (MMMA)
- 4-Methoxy-N-methylamphetamine (PMMA)
- E. H. Woodruff, J. P. Lambooy and W. E. Burt (1940). "Physiologically active amines. III. Secondary and tertiary β-phenylpropylamines and β-phenylisopropylamines." J. Am. Chem. Soc. 62 922-924.
- R. V. Heinzelman (1953). "Physiologically active secondary amines. β-(o-Methoxyphenyl)-isopropyl-N-methylamine and related compounds." J. Am. Chem. Soc. 75 921-925.
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.