Ethinamate

Structural formula
General
Non-proprietary name	Ethinamate
other names	(1-ethynylcyclohexyl) carbamate
Molecular formula	C 9 H 13 NO 2
External identifiers / databases
EC number	204-789-4
ECHA InfoCard	100.004.355
PubChem	3284
DrugBank	DB01031
Wikidata	Q410225
Drug information
Drug class	Hypnotic
properties
Molar mass	167.21 g mol −1
Physical state	firmly
Melting point	96 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: no P-phrases
Toxicological data	108 mg kg −1 ( LD 50 , mouse , iv ) ; 490 mg kg −1 ( LD 50 , mouse , oral ) ; 157 mg kg −1 ( LD 50 , rat , iv ) ; 331 mg kg −1 ( LD 50 , rat , oral ) ; 144 mg kg −1 ( LD 50 , dog , iv ) ; 190 mg kg −1 ( LD 50 , dog , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ethinamate is a drug with short-term sedating and hypnotic effects that has been used to treat insomnia . Regular use leads to tolerance ; the effects usually last no longer than seven days. Ethinamate was patented for Schering in 1957 as a sedative and sleeping aid . It is no longer in trade worldwide.

Presentation and extraction

The synthesis starts from cyclohexanone , which is reacted with ethyne and sodium in liquid ammonia . The carbamate function is then introduced on the resulting 1-ethynylcyclohexanol by reaction with phosgene and ammonia.

Legal status

In the Federal Republic of Germany, ethinamate is a marketable narcotic drug , but not a prescription drug, according to Annex II to Section 1 Paragraph 1 of the Narcotics Act. Possession without permission from the Federal Opium Agency at the Federal Institute for Drugs and Medical Devices is a criminal offense.

Individual evidence

↑ Entry on ethinamate in the DrugBank of the University of Alberta .

↑ ^a ^b Ethinamate data sheet from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).

^ ^A ^b ^c ^d ^e ^f ^g A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890 -031-9 .

↑ ^a ^b Patent US 2,816,910 (Schering 1957).

↑ Narcotics Act 1981, Annex II, as of December 25, 2012.

[1] Entry on ethinamate in the DrugBank of the University of Alberta .