Amylocaine
Amylocaine.svg
Names
IUPAC name
benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.375 Edit this at Wikidata
EC Number
  • 211-411-1
KEGG
UNII
  • InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3 checkY
    Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N checkY
  • InChI=1/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3
    Key: FDMBBCOBEAVDAO-UHFFFAOYAQ
  • O=C(OC(C)(CC)CN(C)C)c1ccccc1
Properties
C14H21NO2
Molar mass 235.32204
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

Synthesis:[3][4][5] Patents:[6][7]
Synthesis:[3][4][5] Patents:[6][7]

Grignard reaction of chloroacetone (1) with one mole of magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol [74283-48-0] (2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol [74347-10-7] (3). These two steps can also be treated as interchangeable. Esterification with benzoyl chloride completed the synthesis of amylocaine (4).

See also

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" Archived 2013-10-05 at the Wayback Machine. 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 (06): 495–498. doi:10.1055/s-1984-30879.
  4. ^ Fourneau Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904 , vol. 138, p. 767.
  5. ^ Zernik Chem. Zentralbl., 1905 , vol. 76, # I p. 1029.
  6. ^ Riedel: DE169746  ().
  7. ^ , DE 169787  ().