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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.
Grignard reaction of
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 an ...
. 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 f ...
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 subarac ...
.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 of chloroacetone
Chloroacetone is a chemical compound with the formula . At STP it is a colourless liquid with a pungent odour. On exposure to light, it turns to a dark yellow-amber colour. It was used as a tear gas in World War I.
Synthesis
Chloroacetone may b ...
(1) with one mole of magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol 4283-48-0
4 (four) is a number, numeral and digit. It is the natural number following 3 and preceding 5. It is the smallest semiprime and composite number, and is considered unlucky in many East Asian cultures.
In mathematics
Four is the smallest c ...
(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
Dimethylaminopivalophenone is an opioid analgesic with a potency ½ that of morphine. It was initially discovered by Russian scientists in 1954 and subsequently rediscovered in the US in 1969. Its LD50 in mice is 83 mg/kg. It has never bee ...
, an opioid with a similar structure–activity relationship The structure–activity relationship (SAR) is the relationship between the chemical structure of a molecule and its biological activity. This idea was first presented by Crum-Brown and Fraser in 1865.
The analysis of SAR enables the determination o ...
(SAR). It is an amine that is a sole methylene spacer
In organic chemistry, a methylene bridge, methylene spacer, or methanediyl group is any part of a molecule with formula ; namely, a carbon atom bound to two hydrogen atoms and connected by single bonds to two other distinct atoms in the rest of ...
shorter.
Notes and references
External links
* * Local anesthetics Benzoate esters Dimethylamino compounds {{nervous-system-drug-stub