Butamirate citrate Chemical Properties

Melting point:

66-68°C

storage temp. 

Hygroscopic, Refrigerator, Under Inert Atmosphere

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White

InChI

InChI=1S/C18H29NO3.C6H8O7/c1-4-17(16-10-8-7-9-11-16)18(20)22-15-14-21-13-12-19(5-2)6-3;7-3(8)1-6(13,5(11)12)2-4(9)10/h7-11,17H,4-6,12-15H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)

InChIKey

JVKMHUAWFDGPTF-UHFFFAOYSA-N

SMILES

C1(C=CC=CC=1)C(CC)C(=O)OCCOCCN(CC)CC.C(O)(C(=O)O)(CC(=O)O)CC(=O)O

Butamirate citrate Usage And Synthesis

Chemical Properties

White Solid

Originator

Sinecod,Hommel,Switz.,1967

Uses

Anxiolytic, Muscle Relaxant

Uses

Butamirate Citrate is a novel antitussive drug. It is used for the symptomatic treatment of non-productive (dry) cough.

Manufacturing Process

18.2 grams of α-phenylbutyric acid chloride are dissolved in 25 ml of toluene. To this solution, there is slowly added a solution of 16.1 grams of diethylaminoethoxyethanol in 25 ml of toluene, the reaction mixture thereby becoming hot. It is then heated for 8 hr under reflux. The reaction mixture, after cooling, is carefully poured onto 75 grams of ice and made alkaline with dilute ammonia. After thorough shaking of the solution, the toluene layer is removed and washed until neutral with water. The toluene solution is treated with carbon and dried over sodium sulfate. The toluene is distilled off from the filtered solution.
The residue is α-phenylbutyric acid diethylaminoethoxyethyl ester. The basic ester is purified by distillation in a high vacuum. 10 grams of ester are added to a solution of 7 grams of citric acid in 30 ml of warm acetone. After standing for some time, the citrate of the ester crystallizes out. After suction filtration and washing with acetone the ester citrate is recrystallized from acetone. The melting point of the citrate is 75°C.

Therapeutic Function

Antitussive

General Description

Butamirate citrate is a non-opioid antitussive with a central effect on receptors in the brain stem. It has also been reported that it reduces bronchospasm with peripheral effect and has anti-inflammatory and anticholinergic effects. Therefore, it is thought to be effective in cough with both acute and chronic etiology.

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