clopenthixol

Chemical Properties

Colorless paste. Soluble in methanol, insoluble in ether. cis(Z)-configuration: [53772-83-1]. Crystallized, melting point 84-85°C. Clopenthixol Dihydrochloride: C22H25C1N2OS2HCl.[633-59-0]. Crystallized from ethanol, melting point 250~260°C (decomposition). Extremely soluble in water, insoluble in alcohol, several insoluble in other organic solvents. Acute toxicity LD50 male mice (mg/kg): 111 IV. cis(Z)-dihydrochloride: [58045-23-1]. Crystalline, melting point 250~260°C (decomposition). Acute toxicity LD50 male mice (mg/kg): 105 IV.

Originator

Ciatyl,Tropon,W. Germany,1961

Uses

Antipsychotic.

Definition

ChEBI: A thioxanthene derivative having a chloro substituent at the 2-position and an alkylidene group at the 10-position with undefined double bond stereochemistry.

Manufacturing Process

A mixture of 31 5 g (0.1 mol) of 2-chloro-9-(3'-dimethylaminopropylidene)- thiaxanthene (MP 97°C) and 100 g of N-(β-hydroxyethyl)piperazine is heated to 130°C and boiled under reflux at this temperature for 48 hours. After cooling,the excess of N-(β-hydroxyethyl)piperazine is evaporated in vacuo, and the residue is dissolved in ether. The ether phase is washed with water and extracted with dilute acetic acid, and 2-chloro-9-[3'-N-(N'-β- hydroxyethyl)piperazinylpropylidene]-thiaxanthene separated from the aqueous acetic acid solution by addition of dilute sodium hydroxide solution to basic reaction. The free base is extracted with ether, the ether phase dried over potassium carbonate, the ether evaporated and the residue dissolved in absolute ethanol. By complete neutralization of the ethanolic solution with a solution of dry hydrogen chloride in absolute ethanol, the dihydrochloride of 2- chloro-9-[3'-N-(N'-β-hydroxyethyl)piperazinylpropylidene]-thiaxanthene is produced and crystallizes out as a white substance melting at about 250°C to 260°C with decomposition. The yield is 32 g.

Therapeutic Function

Antipsychotic