Oxyfedrine

Chemical compound
  • C01DX03 (WHO)
Identifiers
  • (RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
CAS Number
  • 15687-41-9 checkY
PubChem CID
  • 27454
  • 5489013
ChemSpider
  • 4590049
UNII
  • DWL616XF1K
KEGG
  • D08321 checkY
CompTox Dashboard (EPA)
  • DTXSID0023408 Edit this at Wikidata
Chemical and physical dataFormulaC19H23NO3Molar mass313.397 g·mol−13D model (JSmol)
  • Interactive image
  • C[C@@H]([C@@H](c1ccccc1)O)NCCC(=O)c2cccc(c2)OC
InChI
  • 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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Adrenergic receptor modulators
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