15687-41-9

Basic information

• Product Name: Oxyfedrine
• Synonyms: (r-(r*,s*))-3-((2-hydroxy-1-methyl-2-phenylethyl)amino)-1-( 3-methoxyphenyl)-1-propanone;oxyfedrine;Oxyfedrine hydrochloride;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
• CAS NO: 15687-41-9
• Molecular Formula: C19H23NO3
• Molecular Weight: 313.39082
• Mol File: 15687-41-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 475.2 °C at 760 mmHg
• Flash Point: 241.2 °C
• Appearance: /
• Density: 1.122 g/cm³
• Vapor Pressure: 7.78E-10mmHg at 25°C
• Refractive Index: 1.566
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Toluene (Slightly)
• Stability: Hygroscopic, Moisture Sensitive
• CAS DataBase Reference: Oxyfedrine(CAS DataBase Reference)
• NIST Chemistry Reference: Oxyfedrine(15687-41-9)
• EPA Substance Registry System: Oxyfedrine(15687-41-9)

Safety Data

• Hazardous Substances Data: 15687-41-9(Hazardous Substances Data)

Usage

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.

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

InChI:InChI=1/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

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Studies on the action and mechanism of action of Oxyfedrine (cas 15687-41-9) on isolated tracheal chains☆09/05/2019

Oxyfedrine, a β-sympathomimetic drug, did not affect isolated rat and rabbit trachea in concentration from 2.86 × 10−8 to 2.86 × 10−4 M, but on the guinea-pig trachea, it caused a dose dependent relaxation of natural tone in lower concentrations (1.79 × 10−7 to 2.86 × 10−6 M. In higher conc...detailed

Cardiac effects of Oxyfedrine (cas 15687-41-9) in the cat☆09/03/2019

Oxyfedrine, a new aminoketone of the phenylethylamine series, was studied in three cardiac preparations in the cat. Oxyfedrine (0.5 × 10−6 g/ml) exerted a positive inotropic effect while 5.0 × 10−5 g/ml exerted a negative inotropic effect in the cat papillary muscle preparation. Positive inotr...detailed

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Oxyfedrine, 0.5 μg/ml, caused typical but long lasting sympathomimetic effects on guinea-pig atria and trachealis, rabbit atria and duodenum and rat uterus and perfused heart. These effects were antagonised by propranolol. The heart rate and blood pressure of the anaesthetised rat also showed s...detailed