CARBOCROMENE HYDROCHLORIDE Chemical Properties

Melting point:

159-160°

solubility 

Chloroform (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Off-White

Safety Information

Toxicity

LD50 in mice (g/kg): 6.3 orally; 0.528 i.p.; 0.0355 i.v. (Nitz, Potzch)

CARBOCROMENE HYDROCHLORIDE Usage And Synthesis

Originator

Intensain,Hoechst,Switz,1963

Uses

Vasodilator (coronary).

Definition

ChEBI: Carbocromen hydrochloride is a member of coumarins.

Manufacturing Process

18.7 g of 3β-diethylaminoethyl-4-methyl-7-hydroxy-coumarin chlorhydrate are dissolved in 200 cc methyl ethyl ketone and 18 g anhydrous potassium carbonate are added. The mixture is stirred for 1 hour at 70°C and then 12 g bromoacetic acid ethyl ester are allowed to drop in. The reaction mixture is stirred under reflux for 9 hours and then it is filtered off with suction in the heat. The filtrate is concentrated in the vacuum to dryness and the resultant
residue is dissolved in ether. The etheric solution is washed with diluted caustic soda solution for several times and, subsequently, dried with Glauber's salt. By introduction of hydrochloric acid gas into the etheric solution the reaction product is precipitated in the form of chlorhydrate. Yield: 15 g of 3β- diethylaminoethyl-4-methylcoumarin-7-ethyl oxyacetate chlorhydrate having a melting point of 154° to 156°C (= 63% of the theory).
The starting material is produced by reacting resorcinol with 2-(2- diethylaminoethyl)acetic acid ethyl ester.

Therapeutic Function

Coronary vasodilator

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