ETHOPROPAZINE Property

Melting point:

53-55°

Density 

1.1070 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

-20°C

Hazard and Precautionary Statements (GHS)

ETHOPROPAZINE Chemical Properties,Usage,Production

Originator

Parsidol,Warner Lambert,US,1954

Uses

antiparkinsonian, anticholinergic

Definition

ChEBI: A member of the class of phenothiazines that is phenothiazine in which the hydrogen attached to the nitrogen is substituted by a 2-(diethylamino)propyl group. An antimuscarinic, it is used as the hydrochloride for the symptomatic treatment of Parkinson's d sease.

Manufacturing Process

6.2 grams of phenthiazine in 100 cc of warm dry benzene was added during 1 hour with stirring, and in an atmosphere of hydrogen, to the Grignard reagent prepared from 1 gram of magnesium, 6.2 grams of methyl iodide, and 20 cc of dry ether. After boiling for 30 minutes, a solution of 6.6 grams of 2-chloro- 1-diethylamino propane in 10 cc of dry benzene was added during 1 hour to the boiling solution, and heating was maintained for a further 1.5 hours.
The reaction mixture was then cooled and treated with aqueous ammonium chloride and chloroform added to dissolve an oil at the interface of the benzene and aqueous layers. The chloroform-benzene extract was extracted with 2 N hydrochloric acid and the acid extract was basified at 5° to 10°C with 50% aqueous sodium hydroxide.
There was obtained a mixture of N-(2'-diethylamino-2'- methylethyl)phenthiazine and N-(2'-diethylamino-1'-methylethyl)phenthiazine in the form of a viscous yellow oil, BP 202° to 205°C/2 mm. This oil was treated in ethereal solution with ethereal hydrogen chloride and gave a white solid which was fractionally crystallized from ethylene dichloride. The less soluble fraction, N-(2'-diethylamino-2'-methylethyl)phenthiazine hydrochloride formed colorless rhombs, MP 223° to 225°C. The more soluble N-(2'- diethylamino-1'-methylethyl)phenthiazine hydrochloride was obtained as colorless prismatic needles, MP 166° to 168°C.

Therapeutic Function

Antiparkinsonian

Safety Profile

Poison by ingestion, subcutaneous, and intravenous routes. An anticholinergic agent used to treat Parkinson's dsease. When heated to decomposition it emits very toxic fumes of NOx and SOx.