Oxyfedrine
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H23NO3
Molar mass313.397 g·mol−1
3D model (JSmol)
  • C[C@@H]([C@@H](c1ccccc1)O)NCCC(=O)c2cccc(c2)OC
  • InChI=1S/C19H23NO3/c1-14(19(22)15-7-4-3-5-8-15)20-12-11-18(21)16-9-6-10-17(13-16)23-2/h3-10,13-14,19-20,22H,11-12H2,1-2H3/t14-,19-/m0/s1
  • Key:GDYUVHBMFVMBAF-LIRRHRJNSA-N
  (verify)

Oxyfedrine is a vasodilator and a β adrenoreceptor agonist. It was found to depress the tonicity of coronary vessels, improve myocardial metabolism (so that heart can sustain hypoxia better) and also exert a positive chronotropic and inotropic effects, thereby not precipitating angina pectoris. The latter property (positive chronotropic and inotropic effects) is particularly important, because other vasodilators used in angina may be counter productive causing coronary steal phenomenon.

Synergistic effects with antibiotics have been suggested.[1]

Synthesis

Patent:[2]

Mannich condensation of PPA [14838-15-4] (1) with formaldehyde and m-acetanisole (3-Acetylanisole) [586-37-8] (2) yields oxyfedrine (3).

References

  1. ^ Mazumdar K, Dutta NK, Kumar KA, Dastidar SG (April 2005). "In vitro and in vivo synergism between tetracycline and the cardiovascular agent oxyfedrine HCl against common bacterial strains". Biological & Pharmaceutical Bulletin. 28 (4): 713–7. doi:10.1248/bpb.28.713. PMID 15802815.
  2. ^ Thiele Kurt, U.S. patent 3,225,095 (1965 to Degussa).
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