Methoxyphenamine

Methoxyphenamine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 1-(2-methoxyphenyl)-N-methylpropan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.002.035
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Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
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

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]

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

References

  1. ↑ Swiss Pharmaceutical Society (2000). Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. ISBN 3-88763-075-0.
  2. ↑ Wang YH, Bai CX, Hong QY, Chen J (December 2003). "Anti-inflammatory effect of methoxyphenamine compound in rat model of chronic obstructive pulmonary disease". Acta Pharmacologica Sinica. 24 (12): 1324–7. PMID 14653967.
  3. ↑ Woodruff EH, Lambooy JP, Burt WE (April 1940). "Physiologically active amines. III. Secondary and tertiary β-phenylpropylamines and β-phenylisopropylamines". Journal of the American Chemical Society. 62 (4): 922–4. doi:10.1021/ja01861a060.
  4. ↑ Heinzelman RV (February 1953). "Physiologically active secondary amines. β-(o-Methoxyphenyl)-isopropyl-N-methylamine and related compounds". Journal of the American Chemical Society. 75 (4): 921–5. doi:10.1021/ja01100a043.


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