Amylocaine

Amylocaine
Names
IUPAC name
[1-(Dimethylamino)-2-methylbutan-2-yl] benzoate
Other names
Stovaine; 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 235.327 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[contradictory] 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

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. 1 2 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. doi:10.1055/s-1984-30879. ISSN 0039-7881. S2CID 95920500.
  4. 1 2 Fourneau, Ernest (1904). Comptes rendus hebdomadaires des séances de l'Académie des sciences. Vol. 138. Paris: Academy of Sciences, Centre national de la recherche scientifique (CNRS; French National Centre for Scientific Research). p. 767.
  5. ↑ Zernik, F (1905). "?". Chem. Zentralbl. 76 (1): 1029.[full citation needed]
  6. ↑ DE169746C, "Patent number DE169746C". Google Patents.
  7. ↑ DE169787C, "Patent number DE169787C". Google Patents.