ChemicalBook Product Catalog API Circulatory system drugs Angina Pectoris Drugs [R-(R*,S*)]-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-3'-methoxypropiophenone hydrochloride

[R-(R,S)]-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-3'-methoxypropiophenone hydrochloride

Product Name[R-(R*,S*)]-3-[(2-hydroxy-1-methyl-2-phenylethyl)amino]-3'-methoxypropiophenone hydrochloride
CAS16777-42-7
MFC19H23NO3.ClH
MW349.85
EINECS2408281
MOL File16777-42-7.mol

Chemical Properties

Melting point	192-194℃
form	Solid
color	White to off-white

Safety Information

Toxicity

LD50 in mice (mg/kg): 29 i.v. (Hueller)

Usage And Synthesis

Originator

Ildamen,Homburg,W. Germany ,1966

Uses

Oxyfedrine hydrochloride, a vasodilator, is an orally active β-adrenoreceptor agonist. Oxyfedrine decreases the tonicity of coronary vessels. Oxyfedrine hydrochloride can be used in the research of cardiovascular disease[1][2].

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

in vivo

Oxyfedrine (14 mg/kg, p.o., for 3-4 weeks) shows anti-anginal action in cats^[2].
Oxyfedrine (10 mg/kg, i.p., HCT116 cell xenograft mice) suppresses tumor growth when combined with sulfasalazine (SSZ, 350 mg/kg, i.p.)^[1].
Oxyfedrine (1 mg/kg, i.v.) decreases the arterial and venous blood high blood viscosity (HBV) in ice water stress rats^[3].

References

[1] Otsuki Y, et al. Vasodilator oxyfedrine inhibits aldehyde metabolism and thereby sensitizes cancer cells to xCT-targeted therapy. Cancer Sci. 2020 Jan;111(1):127-136. DOI:10.1111/cas.14224
[2] Parratt JR. The haemodynamic effects of prolonged oral administration of oxyfedrine, a partial agonist at beta-adrenoceptors: comparison with propranolol. Br J Pharmacol. 1974 May;51(1):5-13. DOI:10.1111/j.1476-5381.1974.tb09625.x
[3] Yu J, et al. [Effects of oxyfedrine on high blood viscosity and myocardial necrosis induced by epinephrine and ice water stress in rats]. Zhongguo Yao Li Xue Bao. 1993 Jul;14(4):364-6. PMID:8249637
[4] Mackenzie JE, et al. Effects of oxyfedrine on isolated portal vein and other smooth muscles. Br J Pharmacol. 1973 Apr;47(4):827-37. DOI:10.1111/j.1476-5381.1973.tb08210.x

Preparation Products And Raw materials