Α-Eucaine (original) (raw)
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(Redirected from Alpha-Eucaine)
Chemical compound
Pharmaceutical compound
_alpha_-Eucaine
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|
|---|---|
| Clinical data | |
| Trade names | Alpha-Eucaine |
| Other names | α-Eucaine; Eucaine A |
| Identifiers | |
| IUPAC name Methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate | |
| CAS Number | 470-68-8  Y |
| PubChem CID | 5282357 |
| ChemSpider | 4445520 |
| UNII | F4D4T58UFF |
| KEGG | C14166 |
| ChEBI | CHEBI:35059 |
| CompTox Dashboard (EPA) | DTXSID90415220  |
| Chemical and physical data | |
| Formula | C19H27NO4 |
| Molar mass | 333.428 g·mol−1 |
| 3D model (JSmol) | Interactive image |
| SMILES CC1(CC(CC(N1C)(C)C)(C(=O)OC)OC(=O)C2=CC=CC=C2)C | |
| InChI InChI=1S/C19H27NO4/c1-17(2)12-19(16(22)23-6,13-18(3,4)20(17)5)24-15(21)14-10-8-7-9-11-14/h7-11H,12-13H2,1-6H3Key:MJMZACWQGQGLBI-UHFFFAOYSA-N |
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]
Background:[3]
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).
- Eucaine, or β-eucaine, a related local anesthetic
- ^ 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. doi:10.1021/ja02038a002.