| Iupac Name: | [(4''R'',6''S'')-2,2,6-Trimethylpiperidin-4-yl] benzoate |
| Width: | 120 |
| Tradename: | Beta-Eucaine |
| Cas Number: | 500-34-5 |
| Cas Supplemental: | (unspecified isomer) |
| Pubchem: | 808817 |
| Unii: | 7X49L994AY |
| Chemspiderid: | 9945 |
| C: | 15 |
| H: | 21 |
| N: | 1 |
| O: | 2 |
| Smiles: | C[C@H]1C[C@H](CC(N1)(C)C)OC(=O)C2=CC=CC=C2 |
Eucaine, also known as β-eucaine or Betacaine, 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] It is a white, crystalline solid. Prior to World War I, Britain imported eucaine from Germany.[3] During the war, a team including Jocelyn Field Thorpe and Martha Annie Whiteley developed a synthesis in Britain.
The brand name Betacaine can sometimes refer to a preparation containing lidocaine, not eucaine.
Condensation of diacetonamine [625-04-7] (1) with acetaldehyde (paraldehyde) rather than acetone gives the piperidone containing one less methyl group, i.e. 2,2,6-trimethylpiperidin-4-one [3311-23-7] (2). Reduction of the ketone with sodium amalgam gives the alcohol as a mixture of isomers, 2,2,6-trimethylpiperidin-4-ol (3). Benzoylation then affords beta-eucaine (4).