Eucaine

Not to be confused with Alphacaine.
Eucaine
Clinical data
Trade namesBeta-Eucaine
Other names
  • Betacaine
  • Betacain
  • Beta-eucaine
  • Eucaine B
  • Eucain B
  • β-Eucaine
  • Benzoylvinyldiacetonealkamine
Identifiers
  • [(4R,6S)-2,2,6-Trimethylpiperidin-4-yl] benzoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H21NO2
Molar mass247.338 g·mol−1
3D model (JSmol)
  • 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.[3]

The brand name Betacaine can sometimes refer to a preparation containing lidocaine, not eucaine.

Synthesis

Synthesis:[4][5][6]

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).

See also

References

  1. ^ Sneader W (31 October 2005). Drug Discovery: A History. John Wiley & Sons. pp. 127–9. ISBN 978-0-470-01552-0.
  2. ^ Manske RH (12 May 2014). The Alkaloids: Chemistry and Physiology. Elsevier. pp. 213–4. ISBN 978-1-4832-2192-2.
  3. ^ a b Creese MR (1997). "Martha Annie Whiteley (1866-1956): Chemist and Editor" (PDF). Bulletin for the History of Chemistry. 8: 42–45.
  4. ^ Organic medical chemicals, by M. Barrowliff, 98-99, 1921.
  5. ^ Harries, C. (1918). "Untersuchungen über die cyclischen Acetonbasen". Justus Liebig's Annalen der Chemie 417 (2-3): 107–191. doi:10.1002/jlac.19184170202.
  6. ^ King, Harold (1924). "VII.—Stereoisomerism and local anœsthetic action in the β-eucaine group. Resolution of β- and iso-β-eucaine". J. Chem. Soc., Trans. 125 (0): 41–57. doi:10.1039/CT9242500041.
  • The dictionary definition of eucaine at Wiktionary