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| Bevantolol hydrochloride Basic information |
Product Name: | Bevantolol hydrochloride | Synonyms: | 2-PROPANOL, 1-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]AMINO]-3-(3-METHYLPHENOXY)-, HYDROCHLORIDE;1-((2-(3,4-dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanol hydrochloride;BEVANTOLOL HCL;bevantolol hydrochloride;BEVANTOLOLHYDROCHLORIDE(FORR&DONLY);1-[(3,4-Dimethoxyphenethyl)amino]-3-(m-tolyloxy)-2-propanol hydrochloride;CI 775;Cl 775 | CAS: | 42864-78-8 | MF: | C20H28ClNO4 | MW: | 381.89 | EINECS: | | Product Categories: | API | Mol File: | 42864-78-8.mol | |
| Bevantolol hydrochloride Chemical Properties |
Melting point | 137-138° | storage temp. | Sealed in dry,Room Temperature | solubility | DMSO (Slightly), Methanol (Slightly) | form | Solid | color | White to Off-White | Merck | 14,1192 | CAS DataBase Reference | 42864-78-8 |
HS Code | 2922.19.0900 | Toxicity | LD50 orl-rat: 460 mg/kg IYKEDH 26,364,1995 |
| Bevantolol hydrochloride Usage And Synthesis |
Description | Bevantolol hydrochloride is a cardioselective (β1) adrenergic blocker, devoid of intrinsic
sympathomimetic and local anesthetic activities. As with other agents of this category, it
is useful in the treatment of hypertension and angina. | Description | Bevantolol is an antagonist of the β1-adrenergic receptor (β1-AR; Ki = 14.79 nM in rat cortical membranes). It is selective for β1- over β2-ARs (Ki = 588.84 nM), as well as α2-ARs up to 100 μM, but is an antagonist of α1-ARs (Ki = 125.89 nM). Bevantolol inhibits low voltage-activated calcium currents (LVA-ICa) in dissociated rat ventro-medial hypothalamic neurons (IC50 = 40 μM). It inhibits norepinephrine-induced contraction of isolated rabbit thoracic aorta (pA2 = 4.77), isoprenaline-induced inotropic effects in isolated guinea pig right atria (pA2 = 7.74), and isoprenaline-induced relaxation of isolated guinea pig trachea (pA2 = 6.69). Bevantolol (250 mg/kg per day) prevents immobilization stress-induced increases in systolic blood pressure in a rat model of stress-induced hypertension. | Chemical Properties | Off-White Solid | Originator | Warner-Lambert (USA) | Uses | Bevantolol is a cardioselective β-adrenergic blocker. Bevantolol is used as an antianginal, antihypertensive, antiarrhythmic. | Definition | ChEBI: The hydrochloride salt of bevantolol. | Manufacturing Process | To a solution of 50 g (1.25 mol) of NaOH in 1200 ml H2O was added 108 g (1
mol) of m-cresol freshly distilled and at 15°C in one lot 117ml (1.5 mol) of
epichlorohydrin. The emulsion was stirred at room temperature for 16 hours in
a creased flask. The product was taken up in 1000 ml of toluene and washed
with 500 ml water. Distillation yielded 135.7 g=82% of 3-(m-tolyloxy)-1,2-
epoxypropane, b.p. 61°C at 0.05 mm.
Preparation of bevantolol hydrochloride:
To a suitable reactor under a nitrogen blanket is added 13.7 kg of β-(3,4-
dimethoxyphenyl)ethylamine. The amine is cooled to 5°C and 12.5 kg of 3-
(m-tolyloxy)-1,2-epoxypropane is added maintaining the temperature between
5-10°C. After 10 hours, the mixture is seeded with bevantolol free base;
seeding is repeated approximately every 2 hours until it is evident that
crystallization has started. After stirring for 48 hours at 10°C, 26 L of hexane
is added. The temperature is raised to 25°C and stirring is continued for 48
hours. The slurry is filtered and the collected solid is dried under vacuum. The
product is dissolved in 60 L of isopropyl alcohol and the solution is filtered.
The reactor and filter are rinsed with 186 L of isopropyl alcohol and 2.7 kg of
anhydrous hydrogen chloride is added to the combined filtrate. The batch is
heated to reflux for 2 hours. The temperature is adjusted to 65°C and the
solution is seeded with bevantolol hydrochloride crystals. The mixture is held
at this temperature with stirring until a heavy sand-like slurry is present. The
mixture is allowed to cool to ambient temperature without stirring or artificial
cooling. It is then cooled to 20°C. The slurry is centrifuged and the product
rinsed with isopropyl alcohol until the filtrate is colorless. After being vacuum
dried at 50-55°C the product is milled if necessary; yield of bevantolol
hydrochloride 22.7 kg (78.6%); melting point 137-138°C. | Brand name | Vantol (Parke-Davis);Ranestol. | Therapeutic Function | Antiarrhythmic, Beta-adrenergic blocker | Hazard | Moderately toxic by ingestion. | Safety Profile | A poison by intraperitoneal andintravenous route. Moderately toxic by ingestion. Whenheated to decomposition it emits toxic vapors of NOx,HCl, and Cl-. |
| Bevantolol hydrochloride Preparation Products And Raw materials |
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