6709. Normethadone

Nomenclature

CAS number: 467-85-6
6-(Dimethylamino)-4,4-diphenyl-3-hexanone; 1-dimethylamino-3,3-diphenyl-4-hexanone; 1,1-diphenyl-1-(2-dimethylaminoethyl)-2-butanone; isoamidone I; desmethylmethadone; phenyldimazone; Hoechst 10582.
C20H25NO; mol wt 295.42.
C 81.31%, H 8.53%, N 4.74%, O 5.42%.

Description and references

Opioid analgesic used as a cough suppressant. Prepn from 4-bromo-2,2-diphenylbutanenitrile and dimethylamine: Bockmühl, Ehrhart, Ann. 561, 72 (1948); Easton et al., J. Am. Chem. Soc. 74, 5772 (1952). Toxicity data: Eddy et al., J. Pharmacol. Exp. Ther. 98, 121 (1950).

Chemical structure

Properties

Oily liquid, bp3 164-167°. Alkaline reaction.

Derivative

Hydrochloride.

Nomenclature

CAS number: 847-84-7
Ticarda.
C20H25NO.HCl; mol wt 331.88.
C 72.38%, H 7.90%, N 4.22%, O 4.82%, Cl 10.68%.

Properties

Crystals from acetone, mp 174-175°. Sol in water, alcohol. pH of 1% aq soln ≈5. LD50 s.c. in mice: 90 mg/kg (Eddy).

Note

This is a controlled substance (opiate): 21 CFR, 1308.11.

Therapeutic Category

Antitussive.

Keywords

Antitussive