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Amylocaine

Amylocaine

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. It was used mostly in spinal anesthesia.

Synthesis

Amylocaine can be synthesized beginning with chloroacetone (1). 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).

Synthesis of amylocaine

References

  1. Fourneau, E.. (1904). "Stovaïne, anesthésique local". Bulletin des sciences pharmacologiques.
  2. Debue-Barazer, Christine (2007). [http://www.gesnerus.ch/fileadmin/media/pdf/2007_1-2/024-053_Debue.pdf "Les Implications scientifiques et industrielles du succès de la Stovaïne : Ernest Fourneau (1872–1949) et la chimie des médicaments en France"] {{Webarchive. link. (2013-10-05 . ''[[Gesnerus]]'' '''64''' (1-2): 24-53.)
  3. (1984). "A Convenient Synthesis of N,N-Disubstituted Aminomethyltri-n-butylstannanes, Precursors of the Corresponding Lithium Reagents". Synthesis.
  4. Fourneau, Ernest. (1904). "Comptes rendus hebdomadaires des séances de l'Académie des sciences". Academy of Sciences, Centre national de la recherche scientifique (CNRS; [[French National Centre for Scientific Research]]).
  5. Zernik, F. (April 2023). "?". Chem. Zentralbl.
  6. "Patent number DE169746C".
  7. "Patent number DE169787C".
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local-anesthetics benzoate-esters dimethylamino-compounds
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