12-06435. Naepaine [Archived]

Nomenclature

CAS number: 2188-67-2
2-(Pentylamino)ethanol 4-aminobenzoate (ester); p-aminobenzoic acid 2-n-pentylaminoethyl ester; p-aminobenzoic acid 2-n-amylaminoethyl ester; 2-n-amylaminoethyl p-aminobenzoate; 2-n-pentylaminoethyl p-aminobenzoate; Amylsine.
C14H22N2O2; mol wt 250.34.
C 67.17%, H 8.86%, N 11.19%, O 12.78%.

Description and references

Prepn: Goldberg, Whitmore, J. Am. Chem. Soc. 59, 2280 (1937). Prepn of dimorphic cryst forms: Kreider, Menotti, ibid. 64, 1227 (1942).

Chemical structure

Properties

Solid, mp 66°.

Derivative

Hydrochloride.
C14H23ClN2O2; mol wt 286.80.
C 58.63%, H 8.08%, Cl 12.36%, N 9.77%, O 11.16%.

Properties

Dimorphic crystals. Rectangular plates, mp 153.5°; rods, mp 176°. Bitter taste followed by a sense of numbness. Sol in water; sparingly sol in alcohol; insol in ether, chloroform, benzene.

Therapeutic Category

Hydrochloride as local anesthetic.

Therapeutic Category (Veterinary)

Topical anesthetic (ocular).

Keywords

Anesthetic (Local)

Status

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