Butanilicaine

Butanilicaine
Names
	IUPAC name N2-Butyl-N1-(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 [77 °F], 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.^[1]^[2]^[3]

^ "Butanilicaine". Thieme. Retrieved 2024-07-01.
^ Epstein, Elias; Kaminsky, Daniel (1958). "N-(Substituted Aminoacyl)-chloroanilines". Journal of the American Chemical Society. 80 (8): 1892–1895. doi:10.1021/ja01541a028.
^ GB 782971 1957 to Hoechst AG.

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Names

IUPAC name N²-Butyl-N¹-(2-chloro-6-methylphenyl)glycinamide
Systematic IUPAC name 2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide
Identifiers
CAS Number	3785-21-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:55518^Y
ChEMBL	ChEMBL2104238^Y
ChemSpider	21004^Y
PubChem CID	22379
UNII	7X3WV51F4N^Y
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)^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
ATC code	N01BB05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references