α-Eucaine (''alpha''-eucaine) is a drug that was previously used as a
local anesthetic.
It was designed as an
analog
Analog or analogue may refer to:
Computing and electronics
* Analog signal, in which information is encoded in a continuous variable
** Analog device, an apparatus that operates on analog signals
*** Analog electronics, circuits which use analo ...
of
cocaine and was one of the first synthetic chemical compounds to find general use as an anesthetic.
Synthesis
The
Aldol condensation between two equivalents of acetone gives
Mesityl oxide 41-79-7(1) (
isophorone is a side-product of this reaction). Ammonolysis of mesityl oxide formed diacetonamine
25-04-7(2). The reaction of this product with acetone then gives 2,2,6,6-tetramethyl-4-piperidone
26-36-8(3). ''N''-methylation of the secondary amine gives 1,2,2,6,6-pentamethylpiperidin-4-one
554-54-1(4). Cyanohydrin formation give
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
Eucaine, also known as β-eucaine or Betacaine, is a drug that was previously used as a local anesthetic. It was designed as an Functional analog (chemistry), analog of cocaine and was one of the first synthetic chemical compounds to find genera ...
, or β-eucaine, a related local anesthetic
References
Local anesthetics
Piperidines
Benzoate esters
Methyl esters
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