Controlled substance (depressant). Sedative; hypnotic.
ChEBI: Propargyl alcohol in which the methylene hydrogens are substituted by ethyl and 2-chlorovinyl groups. A hypnotic and sedative, it is used for treatment of insomnia in some cases where an intolerance or allergy to more commonly used drugs exists.
Acetylene was passed into a stirred solution of 3.05 grams (0.44 mol) of
lithium in 300 ml of liquid ammonia until the blue color exhibited by the
mixture had disappeared. Ethyl β-chlorovinyl ketone (47.4 grams; 0.40 mol)
dissolved in 50 ml dry ether was then added to the resulting solution of lithium acetylide over a period of 20 minutes, during which the color
deepened through yellow to reddish-brown. The mixture was stirred under
reflux maintained with a Dry Ice condenser for 2 hours. Thereafter, dry ether
(200 ml) was added and the ammonia was permitted to evaporate with
stirring overnight.
The residue was poured into a slurry of ice and water containing 30 grams
(0.50 mol) of acetic acid. After separating the ether layer, the aqueous layer
was washed with two 200 milliliter portions of ether. The combined ether
extracts were washed with saturated sodium bicarbonate solution, dried over
anhydrous magnesium sulfate and evaporated in a stream of pure nitrogen.
Three successive distillations of the residue gave 46.3 grams (80.2% yield) of
a colorless liquid, boiling point 28.5° to 30°C at 0.1 mm Hg.
Poison by ingestion,
subcutaneous, intraperitoneal, and
intravenous routes. Human systemic effects
by ingestion: general anesthesia and
thrombocytopenia (reduction in the number
of blood platelets). Human effects on
newborn by an unspecified route: drug
dependency and Apgar score (condtion of
newborn). Experimental teratogenic and
reproductive effects. When heated to
decomposition it emits toxic fumes of Cl-.
