α-Eucaine
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| Clinical data | |
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| Trade names | Alpha-Eucaine |
| Other names | α-Eucaine; Eucaine A |
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| Chemical and physical data | |
| Formula | C19H27NO4 |
| Molar mass | 333.428 g·mol−1 |
| 3D model (JSmol) | |
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α-Eucaine (alpha-eucaine) is a drug that was previously used as a local anesthetic.[1] It was designed as an analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic.[2]
Synthesis
[edit]_synthesis.svg)
The aldol condensation between two equivalents of acetone gives mesityl oxide (1), with isophorone as a side-product of this reaction. Ammonolysis of mesityl oxide formed diacetonamine (2). The reaction of this product with acetone then gives triacetonamine (3). N-Methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one (4). Cyanohydrin formation gives (5). Esterification of the tertiary alcohol with benzoyl chloride gives (6). Pinner reaction of the nitrile with acidified ethanol affords alpha-eucaine (7).
See also
[edit]- Eucaine, or β-eucaine, a related local anesthetic
References
[edit]- ↑ Sneader W (31 October 2005). Drug Discovery: A History. John Wiley & Sons. pp. 127–9. ISBN 978-0-470-01552-0.
- ↑ Manske RH (12 May 2014). The Alkaloids: Chemistry and Physiology. Elsevier. pp. 213–4. ISBN 978-1-4832-2192-2.
- ↑ Parsons, C. L. (December 1901). "THE IDENTIFICATION AND PROPERTIES OF α- AND β-EUCAINE. 1". Journal of the American Chemical Society. 23 (12): 885–893. Bibcode:1901JAChS..23..885P. doi:10.1021/ja02038a002.