| Identification | Back Directory | [Name]
Oxyfedrine | [CAS]
15687-41-9 | [Synonyms]
oxyfedrine
Oxyfedrine USP/EP/BP
Oxyfedrine hydrochloride
3-[[(1R,2S)-2-Hydroxy-1-methyl-2-phenylethyl]amino]-1-(3-methoxyphenyl)-1-propanone
1-Propanone, 3-[[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]amino]-1-(3-methoxyphenyl)-
3-{[(1S,2R)-2-Hydroxy-1-methyl-2-phenylethyl]amino}-1-[3-(methyloxy)phenyl]propan-1-one
(r-(r*,s*))-3-((2-hydroxy-1-methyl-2-phenylethyl)amino)-1-( 3-methoxyphenyl)-1-propanone | [Molecular Formula]
C19H23NO3 | [MOL File]
15687-41-9.mol | [Molecular Weight]
313.391 |
| Chemical Properties | Back Directory | [Melting point ]
107-109°C | [storage temp. ]
Hygroscopic, -20°C Freezer, Under inert atmosphere | [solubility ]
DMSO (Slightly), Methanol (Slightly), Toluene (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Stability:]
Hygroscopic, Moisture Sensitive |
| Hazard Information | Back Directory | [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 |
| Questions And Answer | Back Directory | [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.
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