Eucaine
Medication
From Wikipedia, the free encyclopedia
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.[3]
- Betacaine
- Betacain
- Beta-eucaine
- Eucaine B
- Eucain B
- β-Eucaine
- Benzoylvinyldiacetonealkamine
- 500-34-5 (unspecified isomer)
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| Trade names | Beta-Eucaine |
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| Formula | C15H21NO2 |
| Molar mass | 247.338 g·mol−1 |
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The brand name Betacaine can sometimes refer to a preparation containing lidocaine, not eucaine.
Synthesis
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Condensation of diacetonamine (1) with acetaldehyde gives the piperidone 2,2,6-trimethylpiperidin-4-one (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).
See also
- α-Eucaine, a related local anesthetic
