Eucaine Explained

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.

Synthesis

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

Notes and References

  1. Book: Sneader W . Drug Discovery: A History. 31 October 2005. John Wiley & Sons. 978-0-470-01552-0. 127–9.
  2. Book: Manske RH . The Alkaloids: Chemistry and Physiology. 12 May 2014. Elsevier. 978-1-4832-2192-2. 213–4.
  3. Creese MR . Martha Annie Whiteley (1866-1956): Chemist and Editor . Bulletin for the History of Chemistry . 1997 . 8 . 42–45 .