α-Eucaine
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| Clinical data | |
|---|---|
| Trade names | Alpha-Eucaine |
| Other names | α-Eucaine; Eucaine A |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
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| ChEBI | |
| E number | {{#property:P628}} |
| CompTox Dashboard (EPA) |
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| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value). |
| 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 | edit source]_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 | edit source]- Eucaine, or β-eucaine, a related local anesthetic
References
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