12-03855. Ethylhydrocupreine [Archived]

Nomenclature

CAS number: 522-60-1
(8α,9R)-6′-Ethoxy-10,11-dihydrocinchonan-9-ol; hydrocupreine ethyl ether; Optoquine; Numoquin.
C21H28N2O2; mol wt 340.46.
C 74.08%, H 8.29%, N 8.23%, O 9.40%.

Description and references

Prepn: Giemsa, Halberkann, Ber. 51, 1325 (1918); Thron, Freund, US 1062203 (1913 to Ver. Chininfabr. Zimmer); Muira, C.A. 41, 4582d (1947). Pharmacology: M. I. Smith, B. Fantus, J. Pharmacol. Exp. Ther. 8, 53 (1916).

Chemical structure

Properties

White bitter cryst powder. mp 123-128° when solvent-free. [α]D25 136.2° (alcohol). Practically insol in water; sol in alcohol, benzene, chloroform, ether, dil acids, oils, fats.

Derivative

Hydrochloride.

Nomenclature

CAS number: 3413-58-9
Neumolisina.
C21H28N2O2.HCl; mol wt 376.92.
C 66.92%, H 7.76%, N 7.43%, O 8.49%, Cl 9.41%.

Properties

Rhombic crystals from acetone + ether, mp 252-254°. [α]D21 123.6° (water). One gram dissolves in 2 ml water, 5 ml alcohol, 2.5 ml chloroform; sparingly sol in dry acetone. Practically insol in ether, petr ether. Aq solns are sterilizable without decompn. Protect from light.

Therapeutic Category

Antiseptic.

Keywords

Antiseptic/Disinfectant; Quinolines

Status

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