Butanilicaine
Appearance
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Names | |
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IUPAC name
N2-Butyl-N1-(2-chloro-6-methylphenyl)glycinamide
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Systematic IUPAC name
2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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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).
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Butanilicaine is a local anesthetic. It is also known by the name Hostacaine.
Synthesis
![](http://upload.wikimedia.org/wikipedia/commons/thumb/6/61/Butanilicaine_synthesis.svg/501px-Butanilicaine_synthesis.svg.png)
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
- ^ Haussler A, Ther L. [Chemical detection of hostacain]. Arzneimittelforschung. 1953;3(12):609-11.
- ^ Epstein, Elias; Kaminsky, Daniel (1958). "N-(Substituted Aminoacyl)-chloroanilines". Journal of the American Chemical Society 80 (8): 1892–1895. doi:10.1021/ja01541a028.
- ^ GB 726080 (1955 to Polymer Corp.)
- ^ GB 759744 (1956 to Cilag)
- ^ GB 782971 1957 to Hoechst AG.
- ^ G. Ehrhart et al., U.S. patent 2,912,460 (1959 to Hoechst).