Α-Eucaine

Not to be confused with Alphacaine.

α-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 names	Alpha-Eucaine
Other names	α-Eucaine; Eucaine A
Identifiers
IUPAC name Methyl 4-benzoyloxy-1,2,2,6,6-pentamethylpiperidine-4-carboxylate
CAS Number	470-68-8 Y
PubChem CID	5282357
ChemSpider	4445520
UNII	F4D4T58UFF
KEGG	C14166
ChEBI	CHEBI:35059
CompTox Dashboard (EPA)	DTXSID90415220
Chemical and physical data
Formula	C19H27NO4
Molar mass	333.428 g·mol−1
3D 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,12-13H2,1-6H3 Key:MJMZACWQGQGLBI-UHFFFAOYSA-N

Synthesis

Background:^[3]

The aldol condensation between two equivalents of acetone gives mesityl oxide (1), with isophorone as a side-product of this reaction. Ammonolysis of mesityl oxide formed diacetonamine (2). The reaction of this product with acetone then gives triacetonamine (3). N-Methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one (4). Cyanohydrin formation gives (5). Esterification of the tertiary alcohol with benzoyl chloride gives (6). Pinner reaction of the nitrile with acidified ethanol affords alpha-eucaine (7).

See also

• Eucaine, or β-eucaine, a related local anesthetic