alpha-eucaine alpha-eucaine alpha-eucaine is a drug that was previously used as a local anesthetic. it was designed as an analog of cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic. alpha-eucaineclinical datatrade namesalpha-eucaineother namesα-eucaine; eucaine aidentifiers iupac name methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate cas number470-68-8pubchem cid5282357chemspider4445520keggc14166chebichebi:35059comptox dashboard (epa)dtxsid90415220 chemical and physical dataformulac19h27no4molar mass333.428 g·mol−13d model (jsmol)interactive image 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,12-13h2,1-6h3key:mjmzacwqgqglbi-uhfffaoysa-n synthesis background: the aldol condensation between two equivalents of acetone gives mesityl oxide (1) (isophorone is a side-product of this reaction). ammonolysis of mesityl oxide formed diacetonamine (2). the reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone (3). n-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one (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).