Propanidide

Structural formula
General
Non-proprietary name	Propanidide
other names	Propyl {4 - ((diethylcarbamoyl) methoxy) -3-methoxyphenyl} acetate
Molecular formula	C 18 H 27 NO 5
Brief description	pale yellow oil
External identifiers / databases
EC number	215-822-7
ECHA InfoCard	100.014.384
PubChem	15004
ChemSpider	14283
Wikidata	Q409719
Drug information
ATC code	N01 AX04
Drug class	Benzene derivative
Mechanism of action	Briefly narcotic
properties
Molar mass	337.40 g mol −1
Physical state	liquid
boiling point	210-212 ° C (93.3 Pa )
solubility	almost insoluble in water; soluble in ethanol and chloroform ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	81 mg kg −1 ( LD 50 , rat , iv ) ; 113 mg kg −1 ( LD 50 , mouse , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propanidide is a derivative of the eugenol contained in clove oil .

properties

Propanidide was used with Cremophor-EL as a solubilizer for short intravenous anesthesia under the brand name Epontol . It was patented by Bayer in 1962 and approved for clinical use in 1965. It spread quickly in the body and brought about a comfortable fall asleep and quick awakening after a few minutes. It was therefore well suited for short surgical procedures (such as reductions).

synthesis

Eugenol is first acetylated ; the acetate is then oxidized , the double bond of the eugenol being cleaved and 4-acetoxy-3-methoxyphenylacetic acid being formed. The acetyl group is split off again; then the free acid is esterified with propanol . Finally, the phenolic hydroxyl group is reacted with chloroacetic acid diethylamide in the sense of a Williamson ether synthesis .

literature

Michael Fresenius; Michael Heck: Repetitorium Anästhesiologie: For the specialist examination and the European diploma (German Edition) , 5th, fully updated edition. Edition, Springer-Verlag , Berlin 2007, ISBN 978-3-540-46575-1 , p. 642 (Accessed December 2, 2009).

Web links

Entry to propanidid at Vetpharm
Entry on propanidide in the ChemIDplus database of the United States National Library of Medicine (NLM)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on propanidide. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Eberhard Schröder, Clemens Rufer, Ralph Schmiechen, Arzneimittelchemie I, Georg Thieme Verlag 1976 ISBN 3-13-520601-7

[roempp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on propanidide. In: Römpp Online . Georg Thieme Verlag, accessed on December 29, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Eberhard Schröder, Clemens Rufer, Ralph Schmiechen, Arzneimittelchemie I, Georg Thieme Verlag 1976 ISBN 3-13-520601-7