3456. Drotebanol

Nomenclature

CAS number: 3176-03-2
(6β)-3,4-Dimethoxy-17-methylmorphinan-6,14-diol; 6β,14-dihydroxy-3,4-dimethoxy-N-methylmorphinan; 14-hydroxydihydro-6β-thebainol 4-methyl ether; dihydro-14-hydroxy-4-O-methyl-6β-thebainol; dihydro-14-hydroxy-6β-thebainol 4-methyl ether; oxymethebanol; Metebanyl (Sankyo).
C19H27NO4; mol wt 333.42.
C 68.44%, H 8.16%, N 4.20%, O 19.19%.

Description and references

Prepn from thebaine: JP 64 26726 (1964 to Sankyo), C.A. 62, 11869b (1965). Metabolism: H. Shindo et al., Yakugaku Zasshi 90, 36 (1970), C.A. 72, 88520q (1970). Pharmacology: S. Kobayashi et al., Arzneim.-Forsch. 20, 43 (1970). Dependence potential in rhesus monkeys: T. Yanagita et al., Bull. Narc. 29, 33 (1977).

Chemical structure

Properties

Minute crystals, very slightly hygroscopic, slightly bitter taste. mp 165.5-166.5°. Slightly sol in water. Freely sol in ethanol, chloroform. Sol in acetone, benzene, toluene. Very slightly sol in ether. LD50 in mice (mg/kg): 1300 orally, 1150 s.c., 91 i.v. (Kobayashi).

Note

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

Therapeutic Category

Antitussive.

Keywords

Antitussive