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). verify (what is ?) Infobox references

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

Synthesis[edit]

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[edit]

^ 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).

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

[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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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^N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:55518^Y
ChEMBL	ChEMBL2104238^N
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). N verify (what is ^YN ?) Infobox references

Butanilicaine

Synthesis[edit]

References[edit]

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