3830. Ethylmorphine

Nomenclature

CAS number: 76-58-4
(5α,6α)-7,8-Didehydro-4,5-epoxy-3-ethoxy-17-methylmorphinan-6-ol; codéthyline.
C19H23NO3; mol wt 313.39.
C 72.82%, H 7.40%, N 4.47%, O 15.32%.

Description and references

Semisynthetic opioid analgesic. Prepd by ethylation of morphine: Baizer, Ellner, J. Am. Pharm. Assoc. 39, 581 (1950); Gorecki, Ann. Pharm. (Poznan) 7, 21 (1969). Toxicity data: M. Aurousseau, J. Navarro, Ann. Pharm. Fr. 15, 640 (1957). GC-MS determn in blood: H. Gjerde et al., Forensic Sci. Int. 51, 105 (1991). Biotransformation and pharmacokinetics: T. A. Aasmundstad et al., Br. J. Clin. Pharmacol. 39, 611 (1995).

Chemical structure

Properties

Crystals from ethanol, mp 199-201°.

Derivative

Hydrochloride dihydrate.

Nomenclature

CAS number: 6746-59-4; 125-30-4 (anhydrous)
C19H23NO3.HCl.2H2O; mol wt 385.88.
C 59.14%, H 7.31%, N 3.63%, O 20.73%, Cl 9.19%.

Properties

Component of Cosylan, Phol-Tux, Sano-Tuss. White to faintly yellow crystalline powder, mp about 123° (dec); anhydrous form, mp about 170° (dec). One gram dissolves in 10 ml water and in 25 ml alcohol; slightly sol in chloroform, ether. LD50 in mice: 264.6 mg/kg s.c.; 0.771 g/kg orally (Aurousseau, Navarro).

Note

This is a controlled substance (opiate): 21 CFR, 1308.12.

Therapeutic Category

Antitussive.

Keywords

Antitussive