Oxyfedrine
Oxyfedrine Basic information
- Product Name:
- Oxyfedrine
- Synonyms:
-
- Oxyfedrine hydrochloride
- (r-(r*,s*))-3-((2-hydroxy-1-methyl-2-phenylethyl)amino)-1-( 3-methoxyphenyl)-1-propanone
- oxyfedrine
- 3-[[(1R,2S)-2-Hydroxy-1-methyl-2-phenylethyl]amino]-1-(3-methoxyphenyl)-1-propanone
- 3-{[(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl]amino}-1-[3-(methyloxy)phenyl]propan-1-one
- 1-Propanone, 3-[[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-(3-methoxyphenyl)-
- Oxyfedrine USP/EP/BP
- CAS:
- 15687-41-9
- MF:
- C19H23NO3
- MW:
- 313.39
- Mol File:
- 15687-41-9.mol
Oxyfedrine Chemical Properties
- Melting point:
- 107-109°C
- Boiling point:
- 475.2±28.0 °C(Predicted)
- Density
- 1.122±0.06 g/cm3(Predicted)
- storage temp.
- Hygroscopic, -20°C Freezer, Under inert atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly), Toluene (Slightly)
- pka
- 13.90±0.20(Predicted)
- form
- Solid
- color
- White to Off-White
- Stability:
- Hygroscopic, Moisture Sensitive
Oxyfedrine Usage And Synthesis
Indications
Oxyfedrine is a vasodilator and has been used in angina pectoris and myocardial infarction.
Mode of action
Vasodilator, beta-sympathomimetic due to its metabolite norephedrine.
Pharmacokinetics
Oxyfedrine is almost completely (75 to 100% of a dose) metabolized to norephedrine (see there), but the organ of biotransformation is not exactly known. It has not yet been decided whether oxyfedrine is metabolized by liver enzymes, as in rats, or is spontaneously degraded eventually in the duodenal fluid before absorption when administered orally. Both organs seem to be involved because the degree of metabolism is the same after parenteral or oral administration; however, entero-hepatic circulation is known.
Side effects
Reversible loss of taste sensation.
Originator
Ildamen,Homburg,W. Germany ,1966
Uses
Oxyfedrine acts as a vasodilator affecting the coronary base flow.
Definition
ChEBI: Oxyfedrine is an aromatic ketone.
Manufacturing Process
45 grams of m-methoxy acetophenone, 8 grams of paraformaldehyde and 30.2 grams of 1 norephedrine were mixed with about 135 cc of isopropanol HCl solution to provide a pH of 4 and the mixture refluxed for 4 hours. The reaction mixture was cooled and the crystals filtered off on a suction filter. 3[1-phenyl-1-hydroxypropyl-(2)-amino]-1-(m-methoxyphenyl)-propanone-(1) HCl was obtained which after recrystallization from methanol had a MP of 190° to 193°C.
Therapeutic Function
Coronary vasodilator
Oxyfedrine Preparation Products And Raw materials
Raw materials
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