Amylocaine

Last updated
Amylocaine
Amylocaine.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-411-1
KEGG
PubChem CID
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 Yes check.svgY
    Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N Yes check.svgY
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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). [3] [4]

Synthesis of amylocaine Amylocaine synthesis.svg
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 . Gesnerus64 (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.

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