13-01506. Butanilicaine [Archived]

Nomenclature

CAS number: 3785-21-5
2-(Butylamino)-N-(2-chloro-6-methylphenyl)acetamide; 2-(butylamino)-6′-chloro-o-acetotoluidide; ω-n-butylaminoacetic acid 2-methyl-6-chloroanilide; 1-(butylaminoacetylamino)-2-chloro-6-methylbenzene; N-(butylaminoacetyl)-6-chloro-o-toluidine.
C13H19ClN2O; mol wt 254.76.
C 61.29%, H 7.52%, Cl 13.92%, N 11.00%, O 6.28%.

Description and references

Prepn: Hussler, Ther, Arzneim.-Forsch. 3, 609 (1953); GB 726080 (1955 to Polymer Corp.); GB 759744 (1956 to Cilag); GB 782971; G. Ehrhart et al., US 2912460 (1957, 1959 both to Hoechst); Epstein, Kaminsky, J. Am. Chem. Soc. 80, 1892 (1958). Structure activity study: P. P. Koelzer, K. H. Wehr, Arzneim.-Forsch. 8, 181 (1958).

Chemical structure

Properties

Crystals, mp 45-46°. bp0.001 145°. bp0.5 166-167°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 6027-28-7
C13H19ClN2O.HCl; mol wt 291.22.
C 53.62%, H 6.92%, Cl 24.35%, N 9.62%, O 5.49%.

Properties

Crystals from ethanol, mp 232°, also reported as mp 236-239° (Epstein, Kaminsky). Soluble in water. Aq soln is neutral.

Derivative

Phosphate.

Nomenclature

CAS number: 2081-65-4
Hostacain (Hoechst).
C13H19ClN2O.H3PO4; mol wt 352.75.
C 44.26%, H 6.29%, Cl 10.05%, N 7.94%, O 22.68%, P 8.78%.

Properties

Crystals, mp 126-127°. LD50 in mice (mg/20 g): 11.4 s.c.; in mice (mg/kg): 30 i.v., 363 i.p.; in rats (mg/kg): 259 i.p. (Koelzer, Wehr).

Therapeutic Category

Anesthetic (local).

Keywords

Anesthetic (Local)

Status

This monograph has been retired and is no longer subject to revision or update.