Methoxyphenamine

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.^[1]

Methoxyphenamine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	R03CB02 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 1-(2-methoxyphenyl)-N-methylpropan-2-amine
CAS Number	93-30-1
PubChem CID	4117
ChemSpider	3974
UNII	J3Z5SRI26Z
CompTox Dashboard (EPA)	DTXSID0023292
ECHA InfoCard	100.002.035
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(CC1=CC=CC=C1OC)NC
InChI InChI=1S/C11H17NO/c1-9(12-2)8-10-6-4-5-7-11(10)13-3/h4-7,9,12H,8H2,1-3H3 Key:OEHAYUOVELTAPG-UHFFFAOYSA-N

It acts as an anti-inflammatory in rats.^[2]

Chemistry

Methoxyphenamine was first synthesized at the Upjohn company by Woodruff and co-workers.^[3] A later synthesis by Heinzelman, from the same company, corrects the melting point given for methoxyphenamine hydrochloride in the earlier paper, and describes an improved synthetic procedure, as well as resolution of the racemic methoxyphenamine.^[4]

See also

• Substituted methoxyphenethylamine
• 2-Methoxyamphetamine (OMA)
• 3-Methoxy-N-methylamphetamine (MMMA)
• 4-Methoxy-N-methylamphetamine (PMMA)