12-06229. Metofoline [Archived]

Nomenclature

CAS number: 2154-02-1
1-(p-Chlorophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline; 1-(p-chlorophenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline; methopholine; Ro-4-1778/1.
C20H24ClNO2; mol wt 345.86.
C 69.45%, H 6.99%, Cl 10.25%, N 4.05%, O 9.25%.

Description and references

Prepn: A. Brossi et al., Helv. Chim. Acta 43, 1459 (1960); H. Besendorf et al., US 3067203 (1962 to Hoffmann-La Roche). Metabolism: G. Sciorelli, Experientia 23, 934 (1967). Review of pharmacology, toxicity and clinical experience: A. Brossi et al., in Analgetics: Medicinal Chemistry Series of Monographs vol. 5, G. deStevens, Ed. (Academic Press, New York, 1965) p 281-330.

Chemical structure

Properties

Colorless leaflets from aqueous methanol, mp 110-111°. LD50 in mice, rats (mg/kg): 180, 400 s.c.; 180, 400 orally; 70, 100 i.p.; in mice, rabbits (mg/kg): 70, 30 i.v. (Brossi, 1965).

Derivative

Hydrochloride.

Properties

Crystals, mp 105-106°. uv max (ethanol): 283, 287 nm.

Therapeutic Category

Analgesic.

Keywords

Analgesic (Non-Narcotic)

Status

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