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Butanilicaine

Names
IUPAC name N-Butyl-N-(2-chloro-6-methylphenyl)glycinamide
Systematic IUPAC name 2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
Identifiers
CAS Number	3785-21-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:55518
ChEMBL	ChEMBL2104238
ChemSpider	21004
PubChem CID	22379
UNII	7X3WV51F4N
CompTox Dashboard (EPA)	DTXSID90191279
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)Key: VWYQKFLLGRBICZ-UHFFFAOYSA-N 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
ATC code	N01BB05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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

Synthesis

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.

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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