alpha-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]

alpha-Eucaine
Clinical data
Trade namesAlpha-Eucaine
Other namesα-Eucaine; Eucaine A
Identifiers
IUPAC name
  • Methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate
CAS Number
PubChem CID
ChemSpider
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H27NO4
Molar mass333.428 g·mol−1
3D model (JSmol)
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,12-13H2,1-6H3
  • Key:MJMZACWQGQGLBI-UHFFFAOYSA-N

Synthesis
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).

See also
  • Eucaine, a related local anesthetic

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. 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.
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