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ETHINAMATE

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ETHINAMATE Basic information

Product Name:
ETHINAMATE
Synonyms:
  • 1-ETHYNYLCYCLOHEXANOL CARBAMATE
  • ETHINAMATE
  • 1-Ethinylcyclohexyl carbamate
  • 1-ethinylcyclohexylcarbamate
  • 1-ethinylcyclohexylcarbonate
  • 1-ethynyl-cyclohexanocarbamate
  • 1-Ethynylcyclohexyl carbamate
  • 1-ethynylcyclohexylcarbamate
CAS:
126-52-3
MF:
C9H13NO2
MW:
167.21
EINECS:
204-789-4
Mol File:
126-52-3.mol
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ETHINAMATE Chemical Properties

Melting point:
96-98°
Boiling point:
bp3 118-122°
Density 
1.1222 (rough estimate)
refractive index 
nD21.5 1.4441 (20% in propylene glycol)
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
13.40±0.50(Predicted)
EPA Substance Registry System
Cyclohexanol, 1-ethynyl-, carbamate (126-52-3)
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Safety Information

Hazard Codes 
T,Xn
Risk Statements 
23/24/25-22
Safety Statements 
22-36/37/39-45
RTECS 
GV9275000
Hazardous Substances Data
126-52-3(Hazardous Substances Data)

MSDS

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ETHINAMATE Usage And Synthesis

Originator

Valmid,Dista,US,1955

Uses

Ethinamate (E890730) is a an active central nervous system depressant used in the treatment of insomnia.

Definition

ChEBI: A carbamate ester that is the 1-vinylcyclohexyl ester of carbamic acid. A short-acting sedative-hypnotic, it was formerly used to treat insomnia.

Manufacturing Process

A solution of 34 cc (0.5 mol) of liquid phosgene in 150 cc of absolute ether is reacted while cooling with a mixture of sodium chloride and ice, first with 62 grams (0.5 mol) of 1-ethinyl cyclohexanol-1 and then with 64 cc (0.5 mol) of quinoline. The precipitated quinoline chlorohydrate is filtered off and the filtrate is reacted with ammonia in ether. In this manner 45 grams of the carbamic acid ester of 1-ethinyl cyclohexanol are obtained. Yield: 53% of the theoretical yield. The ester boils at 108° to 110°C/3 mm and on recrystallization from cyclohexane, yields colorless needles melting at 94° to 96°C.

Therapeutic Function

Sedative

Safety Profile

A deadly human poison. Experimental poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx. See also CARBAMATES.

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