Originator
Parsidol,Warner Lambert,US,1954
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.
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.
