ChemicalBook--->CAS DataBase List--->14133-90-5

14133-90-5

14133-90-5 Structure

14133-90-5 Structure
IdentificationBack Directory
[Name]

4-HYDROXY PROPRANOLOL HCL
[CAS]

14133-90-5
[Synonyms]

4-HYDROXY PROPRANOLOL HCL
(±)-4-Hydroxypropranolol-d7 HCl
4-Hydroxy Propranolol HCl (Rac)
4-HYDROXYPROPRANOLOL HYDROCHLORIDE
(R)-4-Hydroxy Propranolol Hydrochloride
(S)-4-Hydroxy Propranolol Hydrochloride
rac-4-Hydroxy Propranolol Hydrochloride
1-[(4-Hydroxy-1-naphthyl)oxy]-3-(isopropylamino)- 2-propanol hydrochloride
4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride
4-[(2R)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride
[Molecular Formula]

C16H22ClNO3
[MDL Number]

MFCD06656370
[MOL File]

14133-90-5.mol
[Molecular Weight]

311.8
Chemical PropertiesBack Directory
[Appearance]

Off-White Solid
[Melting point ]

156-158°C
[storage temp. ]

2-8°C
[solubility ]

DMSO (Slightly), Methanol (Slightly)
[form ]

Solid
[color ]

Pale Red to Black
[Stability:]

Hygroscopic
Hazard InformationBack Directory
[Chemical Properties]

Off-White Solid
[Uses]

A metabolite of Propranolol.
[Uses]

The main metabolite of (R)-Propranolol
[Uses]

The main metabolite of (S)-Propranolol
[Biological Activity]

(±)-4-hydroxy propranolol, an active metabolite of propranolol, blocks β1- and β2-adrenergic receptors (β1-ars, β2-ars). also, (±)-4-hydroxy propranolol has antioxidant properties at micromolar concentrations. β1- and β2-ars, expressed in cardiac myocytes, mediate an increase in contractility by gs-dependent coupling to adenylyl cyclase.
[in vitro]

compared to the control, (±)-4-hydroxy propranolol potently blocked the lipid peroxidation in a concentration-dependent fashion in endothelial cells. when pretreated with (±)-4-hydroxy propranolol at 0.067 to 6.7 μm, the degrees of protection were increased against the glutathione loss in the endothelial cells. additionally, (±)-4-hydroxy propranolol effectively preserved the loss of cell survival because of the radical stress [1].
[in vivo]

rats were injected intravenously with (±)-4-hydroxy propranolol into the femoral vein at 0.1 ml/100 g. (±)-4-hydroxy propranolol induced an increase in heart rate in a dose-dependent manner in rats depleted of catecholamines, which suggested that (±)-4-hydroxy propranolol had intrinsic sympathomimetic activity. the response of (±)-4-hydroxy propranolol was inhibited when rats were pretreated with 0.5 mg/kg propranolol [2].
[IC 50]

1.1 μm: inhibits lipid peroxidation in endothelial cells.
[References]

[1]. mak, i. potent antioxidant properties of 4-hydroxyl-propranolol. journal of pharmacology and experimental therapeutics. 2003; 308(1): 85-90.
[2]. fitzgerald, j., & o'donnell, s. pharmacology of 4-hydroxypropranolol, a metabolite of propranolol. british journal of pharmacology. 1971; 43(1): 222-235.
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