Oxolamine Chemical Properties

Melting point:

25°C

Boiling point:

bp0.4 127°

Density 

1.0516 (rough estimate)

refractive index 

1.5310 (estimate)

pka

9.40±0.25(Predicted)

form 

Liquid

LogP

2.393

CAS DataBase Reference

959-14-8(CAS DataBase Reference)

Safety Information

Toxicity

LD50 oral in rat: > 2gm/kg

Oxolamine Usage And Synthesis

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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