7807. Proparacaine

Nomenclature

CAS number: 499-67-2
3-Amino-4-propoxybenzoic acid 2-(diethylamino)ethyl ester; 2-(diethylamino)ethyl 3-amino-4-propoxybenzoate; proxymetacaine.
C16H26N2O3; mol wt 294.39.
C 65.28%, H 8.90%, N 9.52%, O 16.30%.

Description and references

Prepn of the hydrochloride: Clinton et al., J. Am. Chem. Soc. 74, 592 (1952). Pharmacology: McIntyre, Sievers, J. Pharmacol. Exp. Ther. 63, 369 (1938). Comprehensive description: D. B. Whigan, Anal. Profiles Drug Subs. 6, 423-456 (1977).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 5875-06-9
Ak-Taine (Akorn); Alcaine (Alcon); Ophthaine (BMS); Ophthetic (Allergan).
C16H26N2O3.HCl; mol wt 330.85.
C 58.08%, H 8.23%, N 8.47%, O 14.51%, Cl 10.72%.

Properties

Prisms from abs alcohol + ethyl acetate, mp 182.0-183.3°. uv max (methanol): 225, 270, 300 nm. Sol in water, warm alcohol, methanol. Insol in ether, benzene. Solns are neutral to litmus. pKa 3.2.

Therapeutic Category

Topical anesthetic (ophthalmic).

Therapeutic Category (Veterinary)

Anesthetic (local).

Keywords

Anesthetic (Local)