Chemistry:Oxyfedrine

Short description: Chemical compound

Oxyfedrine

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	C01DX03 (WHO)
Identifiers
IUPAC name (RS)-3-[(2-Hydroxy-1-methyl-2-phenylethyl)amino]-1-(3-methoxyphenyl)propan-1-one
CAS Number	15687-41-9 Y
PubChem CID	27454 5489013
ChemSpider	4590049
UNII	DWL616XF1K
KEGG	D08321 Y
Chemical and physical data
Formula	C19H23NO3
Molar mass	313.397 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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
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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.

Synthesis

Patent:

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