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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 |
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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]
The Aldol condensation between two equivalents of acetone gives Mesityl oxide [141-79-7] (1) ( isophorone is a side-product of this reaction). Ammonolysis of mesityl oxide formed diacetonamine [625-04-7] (2). The reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone [826-36-8] (3). N-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one [5554-54-1] (4). Cyanohydrin formation gives CID:434556 (5). Esterification of the tertiary alcohol with benzoyl chloride gives (6). Pinner reaction of the nitrile with EtOH/H+ affords alpha-eucaine (7).