1523. Butethamine

Nomenclature

CAS number: 2090-89-3
2-[(2-Methylpropyl)amino]ethanol 4-aminobenzoate (ester); 2-(isobutylamino)ethanol p-aminobenzoate (ester); 2-(isobutylamino)ethyl p-aminobenzoate.
C13H20N2O2; mol wt 236.31.
C 66.07%, H 8.53%, N 11.85%, O 13.54%.

Description and references

Prepn of the hydrochloride: Goldberg, US 2139818 (1938 to Novocol Chem.); J. Büchi et al., Arzneim.-Forsch. 14, 161 (1964); 16, 1657 (1966).

Chemical structure

Derivative

Formate.
C13H20N2O2.CH2O2; mol wt 282.34.
C 59.56%, H 7.85%, N 9.92%, O 22.67%.

Properties

mp 136-139°. Freely sol in water and alcohol. Slightly sol in chloroform, ether; very slightly sol in benzene. pH (1% aq soln): about 6.1.

Derivative

Hydrochloride.

Nomenclature

CAS number: 553-68-4
Ibylcaine; Monocaine (Novocol).
C13H20N2O2.HCl; mol wt 272.77.
C 57.24%, H 7.76%, N 10.27%, O 11.73%, Cl 13.00%.

Properties

mp 192-196°. Sol in water, slightly sol in alcohol, chloroform, benzene. Practically insol in ether. pH (1% aq soln): about 4.7.

Derivative

meta-Isomer hydrochloride.

Nomenclature

CAS number: 553-58-2
Metabutethamine hydrochloride.
C13H20N2O2.HCl; mol wt 272.77.
C 57.24%, H 7.76%, N 10.27%, O 11.73%, Cl 13.00%.

Properties

Bitter crystals, mp 181-184°. Sol in water. pH of 1:50 aq soln about 6.2. Slightly sol in alcohol, acetone, chloroform.

Therapeutic Category

Anesthetic (local).

Therapeutic Category (Veterinary)

Local anesthetic for nerve block.

Keywords

Anesthetic (Local)