5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Property

Melting point:

141-142 °C

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

color 

Crystals. Sltly sol in water and alc

Safety

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36

WGK Germany 

3

RTECS 

RO0720000

Toxicity

TDLo orl-rat: 15 g/kg/1Y-I:CAR EMPSAL 2,1,63 orl-rat LD50:1650 mg/kg BJPCAL 16,209,61

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

5-[2-(DIETHYLAMINO)ETHYL]-3-PHENYL-1,2,4-OXADIAZOLE CITRATE SALT Chemical Properties,Usage,Production

Originator

Bredon,Organon

Uses

Oxolamine Citrate, is a antiinflammatory drug used as a cough suppressant.

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

Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx. See also AMINES and other oxolamhe entries