Chemistry:Alpha-Eucaine

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Short description: Chemical compound


alpha-Eucaine
Alpha-Eucaine.svg
Clinical data
Trade namesAlpha-Eucaine
Other namesα-Eucaine; Eucaine A
Identifiers
CAS Number
PubChem CID
ChemSpider
KEGG
ChEBI
Chemical and physical data
FormulaC19H27NO4
Molar mass333.428 g·mol−1
3D model (JSmol)

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]

Synthesis

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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