| Identification | More | [Name]
Oxolamine | [CAS]
959-14-8 | [Synonyms]
5-[2-(diethylamino)ethyl]-3-phenyl-1,2,4-oxadiazole
OXOLAMINE
1,2,4-OXADIAZOLE,5-(2-DIETHYLAMINO)ETHYL)-3-PHENYL-
Oxolamine (base and/or unspecified salts)
683 M
683M
AF-438 | [EINECS(EC#)]
213-493-4 | [Molecular Formula]
C14H19N3O | [MDL Number]
MFCD00866857 | [Molecular Weight]
245.32 | [MOL File]
959-14-8.mol |
| Hazard Information | Back Directory | [Originator]
Bredon,Organon | [Uses]
Oxolamine is a antiinflammatory drug used as a cough suppressant. | [Definition]
ChEBI: N,N-diethyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)ethanamine is an oxadiazole and a ring assembly. | [Manufacturing Process]
18.7 g 3-chloro-propionyl chloride in 50 ml of dry ether was added dropwise with stirring to the cooled with ice solution 40 g of N-hydroxybenzamidine in 450 ml dry ester. A dense precipitate had fallen. The mixture was stirred 0.5 hour at room temperature and then was filtered off. The precipitate was thoroughly washed with water for a removal hydrochloride of starting Nhydroxybenzamidine whereas N-(amino)phenylmethylene-3-Cl-propionamide didnt solve. It was dried in vacuum over P2O5. Yield of clean product 94% from theoretical. MP: 98°-99°C. The solution of 9.2 g diethyl amine in 50 ml dry benzene was added dropwise to a suspension of above prepared N(amino)phenylmethylene-3-Cl-propionamide in dry benzene with stirring and cooling.
The mixture was warmed and stirred else 2 hours after adding. Then it was cooled, washed two times with water and dried over CaCl2. Then the solvent was removed. The residue was distilled in vacuum. Diethyl-[2-(3phenyl[1,2,4]oxadiasol-5)ethyl]amine (oxolamine) had BP: 127°C/0.4 mm. Yield 10.5 g.
| [Therapeutic Function]
Antitussive, Antiinflammatory | [Safety Profile]
Moderately toxic by ingestion and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. |
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