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.[1] It was used mostly in spinal anesthesia.[2]

Amylocaine
Names
IUPAC name
benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.375
EC Number
  • 211-411-1
KEGG
PubChem CID
UNII
InChI
  • 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 Y
    Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N Y
  • 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
SMILES
  • O=C(OC(C)(CC)CN(C)C)c1ccccc1
Properties
Chemical formula
 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 YN ?)
Infobox references

Synthesis
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 ().
  • Smith, Maurice I.; Hatcher, Robert A. (January 1917). "A Contribution to the Pharmacology of Stovaine". Journal of Pharmacology and Experimental Therapeutics. 9 (4): 231–240.
  • Ball, Christine M.; Westhorpe, Rod N. (2004). "Local Anaesthesia after Cocaine". Anaesthesia and Intensive Care. 32 (2): 157. PMID 15957711.
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