Amylocaine Explained

Amylocaine was the first synthetic local anesthetic. It was synthesized and patented under the name Stovaine by Ernest Fourneau at the Pasteur Institute in 1903.^[1] It was used mostly in spinal anesthesia.^[2]

Synthesis

Amylocaine can be synthesized beginning with chloroacetone (1).^{[3] [4] [5] [6] [7]} Grignard reaction of chloroacetone with magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol (2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol (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 chemical structure

External links

• A Contribution to the Pharmacology of Stovaine . Maurice I. . Smith . Robert A. . Hatcher . Journal of Pharmacology and Experimental Therapeutics . January 1917 . 9 . 4 . 231–240 .
• Local Anaesthesia after Cocaine . Christine M. . Ball . Rod N. . Westhorpe . Anaesthesia and Intensive Care . 2004 . 32 . 2 . 157 . 10.1177/0310057X0403200201 . 15957711 . free .

Notes and References

1. Fourneau, E. . 1904 . Stovaïne, anesthésique local . Bulletin des sciences pharmacologiques . 10 . 141–148 .
2. 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.
3. Quintard . Jean-Paul . Elissondo . Bernard . Jousseaume . Bernard . 1984 . A Convenient Synthesis of N,N-Disubstituted Aminomethyltri-n-butylstannanes, Precursors of the Corresponding Lithium Reagents . Synthesis . 1984 . 6 . 495–498 . 10.1055/s-1984-30879 . 95920500 . 0039-7881.
4. Book: Fourneau, Ernest . Comptes rendus hebdomadaires des séances de l'Académie des sciences . 1904 . Academy of Sciences, Centre national de la recherche scientifique (CNRS; French National Centre for Scientific Research) . 138 . Paris . 767.
5. Zernik . F. Chem. Zentralbl . ? . 1905 . 76 . 1 . 1029.
6. DE169746C. Patent number DE169746C. . Google Patents.
7. DE169787C. Patent number DE169787C. . Google Patents.