Butanilicaine

Last updated
Butanilicaine
Butanilicaine.svg
Names
IUPAC name
N2-Butyl-N1-(2-chloro-6-methylphenyl)glycinamide
Systematic IUPAC name
2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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) Yes check.svgY
    Key: VWYQKFLLGRBICZ-UHFFFAOYSA-N Yes check.svgY
  • 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
  • CCCCNCC(=O)NC1=C(C=CC=C1Cl)C
Properties
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).

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

Synthesis

Butanilicaine synthesis.svg

Amide formation by the combination of 2-chloro-6-methylaniline (1) and chloroacetyl chloride (2) gives the intermediate (3), which is used to alkylate N-butylamine (4) to yield butanilicaine. [1] [2] [3]

References

  1. ↑ "Butanilicaine". Thieme. Retrieved 2024-07-01.
  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 782971 1957 to Hoechst AG.



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