Structural Formula Vector Image
Title: Butacaine
CAS Registry Number: 149-16-6
CAS Name: 3-(Dibutylamino)-1-propanol 4-aminobenzoate
Additional Names: 3-(p-aminobenzoxy)-1-di-n-butylaminopropane; dibutylaminopropyl-p-aminobenzoate; p-aminobenzoyldibutylaminopropanol
Trademarks: Butelline
Molecular Formula: C18H30N2O2
Molecular Weight: 306.44
Percent Composition: C 70.55%, H 9.87%, N 9.14%, O 10.44%
Literature References: Prepd from p-nitrobenzoyl chloride and g-di-n-butylaminopropanol followed by reduction of the NO2 group to NH2: O. Kamm et al., US 1358751; Adams, Volwiler, US 1676470; A. Weston, US 2437984 (1920, 1928, 1948 all to Abbott); Burnett et al., J. Am. Chem. Soc. 59, 2248 (1937); Kaye, Roberts, ibid. 73, 4762 (1951). Toxicity study: Schmidt et al., Toxicol. Appl. Pharmacol. 1, 454 (1956).
Properties: Liquid, bp0.11 178-182°.
Boiling point: bp0.11 178-182°
Derivative Type: Sulfate
CAS Registry Number: 149-15-5
Trademarks: Butyn Sulfate (Abbott)
Molecular Formula: (C18H30N2O2)2.H2SO4
Molecular Weight: 710.96
Percent Composition: C 60.82%, H 8.79%, N 7.88%, O 18.00%, S 4.51%
Properties: Crystals from n-propanol, mp 138.5-139.5°. Also reported as mp 100-103°. Produces numbness of tongue on tasting. Affected by light. One gram dissolves slowly in somewhat less than 1 ml water, more rapidly on heating. Quite sol in warm alc, in acetone; slightly sol in chloroform. Practically insol in ether. Aq soln is practically neutral to litmus and may be boiled for sterilization without dec. LD50 i.v. in mice: 12.4 mg/kg (Schmidt). Pharmaceutical Incompat. Alkalies and alkaline-reacting substances liberate the free base as an oily liquid from solns. Bicarbonates produce a precipitate of butacaine carbonate. Iodine gives a brown precipitate. Chlorides form the almost insol butacaine chloride which may precipitate.
Melting point: mp 138.5-139.5°; mp 100-103°
Toxicity data: LD50 i.v. in mice: 12.4 mg/kg (Schmidt)
Derivative Type: Hydrochloride
Molecular Formula: C18H30N2O2.HCl
Molecular Weight: 342.90
Percent Composition: C 63.05%, H 9.11%, N 8.17%, O 9.33%, Cl 10.34%
Properties: Crystals from ethanol, mp 157-158.5°.
Melting point: mp 157-158.5°
Therap-Cat: Anesthetic (local).
Therap-Cat-Vet: Anesthetic (local).
Keywords: Anesthetic (Local).

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