Butanilicaine

Butanilicaine is a local anesthetic. It is also known by the name Hostacaine.

Butanilicaine
Names
Preferred IUPAC name
2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C13H19ClN2O/c1-3-4-8-15-9-12(17)16-13-10(2)6-5-7-11(13)14/h5-7,15H,3-4,8-9H2,1-2H3,(H,16,17) Y
    Key: VWYQKFLLGRBICZ-UHFFFAOYSA-N Y
  • InChI=1/C13H19ClN2O/c1-3-4-8-15-9-12(17)16-13-10(2)6-5-7-11(13)14/h5-7,15H,3-4,8-9H2,1-2H3,(H,16,17)
    Key: VWYQKFLLGRBICZ-UHFFFAOYAQ
SMILES
  • CCCCNCC(=O)NC1=C(C=CC=C1Cl)C
Properties
Chemical formula
 C13H19ClN2O
Molar mass 254.75576
Pharmacology
N01BB05 (WHO)
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
Thieme Synthesis:[1][2] Patents:[3][4][5][6]

The amide formation between 2-Chloro-6-Methylaniline [87-63-8] (1) and Chloroacetyl chloride (2) gives 2-Chloro-n-(2-chloro-6-methylphenyl)acetamide [6307-67-1] (3). Alkylation with N-Butylamine (4) completed the synthesis of Butanilicaine (5).

References
  1. Haussler A, Ther L. [Chemical detection of hostacain]. Arzneimittelforschung. 1953;3(12):609-11.
  2. Epstein, Elias; Kaminsky, Daniel (1958). "N-(Substituted Aminoacyl)-chloroanilines". Journal of the American Chemical Society 80 (8): 1892–1895. doi:10.1021/ja01541a028.
  3. GB 726080 (1955 to Polymer Corp.)
  4. GB 759744 (1956 to Cilag)
  5. GB 782971 1957 to Hoechst AG.
  6. G. Ehrhart et al., U.S. Patent 2,912,460 (1959 to Hoechst).



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