| Identification | Back Directory | [Name]
Bevantolol hydrochloride | [CAS]
42864-78-8 | [Synonyms]
CI 775
Cl 775
Vantol
NC 1400
Ranestol
Sentiloc
BEVANTOLOL HCL
NC-1400 hydrochloride
bevantolol hydrochloride
Bevantolol hydrochloride
1-5 g
Bevantolol hydrochloride, >=99%
Bevantolol hydrochloride USP/EP/BP
BEVANTOLOLHYDROCHLORIDE(FORR&DONLY)
DiMethoxyphenethyl)aMino]-3-(M-tolyloxy)-2-propanol Hydrochloride
1-((3,4-DiMethoxyphenethyl)aMino)-3-(M-tolyloxy)propan-2-ol hydrochloride
1-[(3,4-Dimethoxyphenethyl)amino]-3-(m-tolyloxy)-2-propanol hydrochloride
1-((2-(3,4-dimethoxyphenyl)ethyl)amino)-3-(3-methylphenoxy)-2-propanol hydrochloride
2-PROPANOL, 1-[[2-(3,4-DIMETHOXYPHENYL)ETHYL]AMINO]-3-(3-METHYLPHENOXY)-, HYDROCHLORIDE | [Molecular Formula]
C20H28ClNO4 | [MDL Number]
MFCD00941389 | [MOL File]
42864-78-8.mol | [Molecular Weight]
381.89 |
| Chemical Properties | Back Directory | [Melting point ]
137-138° | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [color ]
White to Off-White | [Water Solubility ]
H2O: 2mg/mL, clear | [Merck ]
14,1192 | [InChI]
InChI=1S/C20H27NO4.ClH/c1-15-5-4-6-18(11-15)25-14-17(22)13-21-10-9-16-7-8-19(23-2)20(12-16)24-3;/h4-8,11-12,17,21-22H,9-10,13-14H2,1-3H3;1H | [InChIKey]
FJTKCFSPYUMXJB-UHFFFAOYSA-N | [SMILES]
C1(OC)C=CC(CCNCC(O)COC2=CC=CC(C)=C2)=CC=1OC.Cl | [CAS DataBase Reference]
42864-78-8 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
Bevantolol is a cardioselective β-adrenergic blocker. Bevantolol is used as an antianginal, antihypertensive, antiarrhythmic. | [Definition]
ChEBI: The hydrochloride salt of bevantolol. | [Brand name]
Vantol (Parke-Davis). | [Hazard]
Moderately toxic by ingestion. | [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. | [Originator]
Warner-Lambert (USA) | [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. | [Therapeutic Function]
Antiarrhythmic, Beta-adrenergic blocker | [Safety Profile]
A poison by intraperitoneal andintravenous route. Moderately toxic by ingestion. Whenheated to decomposition it emits toxic vapors of NOx,HCl, and Cl-. | [storage]
Store at -20°C | [References]
[1] Tetrahedron Asymmetry, 2016, vol. 27, # 9-10, p. 397 - 403
[2] Journal of Molecular Structure, 2009, vol. 936, # 1-3, p. 171 - 176 |
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| Company Name: |
J & K SCIENTIFIC LTD.
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| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
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