CHLORISONDAMINE DIIODIDE

Originator

Ecolid Chloride,Ciba,US,1956

The Uses of CHLORISONDAMINE DIIODIDE

Chlorisondamine Diiodide is being used as an intracranial injection to study the localization and analysis of small drug molecules in rat brain tissue.

The Uses of CHLORISONDAMINE DIIODIDE

Biochemical probe in nicotinic receptor studies.

Manufacturing Process

50 parts by weight of 3,4,5,6-tetrachlorophthalic anhydride is added with stirring and cooling to 30 parts by volume of 2-dimethylaminoethyl amine. The mixture is heated at 170°C for 4 minutes and the oily residue then dissolved in 200 parts by volume of hot ethanol. On cooling, N-(2'- dimethylaminoethyl)-3,4,5,6-tetrachlorophthalimide separates. It crystallizes from ethanol and melts at 184°-186°C.
6 parts by weight of N-(2'-dimethylaminoethyl)-3,4,5,6-tetrachlorophthalimide is extracted continuously with 300 parts by volume of dry ether in which have been dissolved 3.1 parts by weight of lithium aluminum hydride. After 48 hours the excess lithium aluminum hydride is destroyed by cautious addition of 9 parts by volume of ethyl acetate while stirring. There is then added in succession with stirring 3 parts by volume of water, 6 parts by volume of 15% aqueous sodium hydroxide and 9 parts by volume of water. The granular precipitate of lithium and aluminum salts are filtered and washed with ether. The ether is distilled off, yielding the crude, oily 4,5,6,7-tetrachloro-2-(2'- dimethylaminoethyl)-isoindoline. The above base is dissolved in 25 parts by volume of 90% ethanol and refluxed 2 hours with 6 parts by volume of methyl iodide. 4,5,6,7-tetrachloro-2-(2'-dimethylaminoethyl)-isoindoline dimethiodide separates during the reaction. It is collected by filtration and recrystallized
from a mixture of ethanol and water; MP 244°-246°C. 4,5,6,7-tetrachloro-2-(2'-dimethylaminoethyl)-isoindoline dimethochloride is prepared by shaking an aqueous solution of the dimethiodide with an excess of freshly prepared silver chloride and evaporating to dryness the aqueous solution after removal of the silver salts. 4,5,6,7-tetrachloro-2-(2'- dimethylaminoethyl)-isoindoline dimethochloride is recrystallized from ethanolethylacetate; MP 276°-280°C.

Therapeutic Function

Antihypertensive

Biological Activity

An exceptionally long lasting nicotinic antagonist (IC 50 ~ 1.6 mM); blockade of central nicotinic responses induced by chlorisondamine can persist for several weeks.