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Amylocaine was the first synthetic
"Les Implications scientifiques et industrielles du succès de la Stovaïne : Ernest Fourneau (1872-1949) et la chimie des médicaments en France"
. ''Gesnerus'' 64 (1-2): 24-53.
local anesthetic
A local anesthetic (LA) is a medication that causes absence of pain sensation. In the context of surgery, a local anesthetic creates an absence of pain in a specific location of the body without a loss of consciousness, as opposed to a general a ...
. It was synthesized and patented under the name Stovaine by Ernest Fourneau
Ernest Fourneau (4 October 1872 – 5 August 1949) was a French pharmacist graduated in Pharmacy 1898 for the Paris university specialist in medicinal chemical and pharmacology who played a major role in the discovery of synthetic local anesthetic ...
at the Pasteur Institute
The Pasteur Institute (french: Institut Pasteur) is a French non-profit private foundation dedicated to the study of biology, micro-organisms, diseases, and vaccines. It is named after Louis Pasteur, who invented pasteurization and vaccines ...
in 1903. It was used mostly in spinal anesthesia
Spinal anaesthesia (or spinal anesthesia), also called spinal block, subarachnoid block, intradural block and intrathecal block, is a form of neuraxial regional anaesthesia involving the injection of a local anaesthetic or opioid into the subara ...
.Debue-Barazer, Christine (2007)"Les Implications scientifiques et industrielles du succès de la Stovaïne : Ernest Fourneau (1872-1949) et la chimie des médicaments en France"
. ''Gesnerus'' 64 (1-2): 24-53.
Synthesis
Grignard reaction
The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides (Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of ...
of chloroacetone
Chloroacetone is a chemical compound with the chemical formula, formula . At Standard conditions for temperature and pressure, STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It wa ...
(1) with one mole of magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol 4283-48-0(2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol 4347-10-7(3). These two steps can also be treated as interchangeable. Esterification with benzoyl chloride completed the synthesis of amylocaine (4).
See also
* Dimethylaminopivalophenone, an opioid with a similar structure–activity relationship (SAR). It is an amine that is a sole methylene spacer shorter.Notes and references
External links
* * Local anesthetics Benzoate esters Dimethylamino compounds {{nervous-system-drug-stub