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Amylocaine

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(Redirected from Stovaine)
Amylocaine
Names
IUPAC name benzoate
Other names Stovaine; Benzoic acid ester
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.375 Edit this at Wikidata
EC Number
  • 211-411-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N
  • InChI=1/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3Key: FDMBBCOBEAVDAO-UHFFFAOYAQ
SMILES
  • O=C(OC(C)(CC)CN(C)C)c1ccccc1
Properties
Chemical formula C14H21NO2
Molar mass 235.327 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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

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 (6): 495–498. doi:10.1055/s-1984-30879. ISSN 0039-7881. S2CID 95920500.
  4. ^ 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.
  6. DE169746C, "Patent number DE169746C" . Google Patents.
  7. DE169787C, "Patent number DE169787C" . Google Patents.

External links

Local anesthetics (primarily sodium channel blockers) (N01B)
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
Amides
Combinations
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