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 | |||||||||||||||||||
|
|||||||||||||||||||
Drug information | |||||||||||||||||||
ATC code | |||||||||||||||||||
Drug class |
Benzene derivative |
||||||||||||||||||
Mechanism of action |
Briefly narcotic |
||||||||||||||||||
properties | |||||||||||||||||||
Molar mass | 337.40 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
||||||||||||||||||
boiling point | |||||||||||||||||||
solubility |
|
||||||||||||||||||
safety instructions | |||||||||||||||||||
|
|||||||||||||||||||
Toxicological data | |||||||||||||||||||
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