5863. Meptazinol

Nomenclature

CAS number: 54340-58-8
3-(3-Ethylhexahydro-1-methyl-1H-azepin-3-yl)phenol; 1-methyl-3-ethyl-3-(m-hydroxyphenyl)hexahydro-1H-azepine.
C15H23NO; mol wt 233.35.
C 77.21%, H 9.93%, N 6.00%, O 6.86%.

Description and references

Mixed opioid agonist-antagonist. Prepn of the hydrobromide: J. F. Cavalla, A. C. White, DE 1941534; eidem, US 3729465 (1970, 1973 both to Wyeth); of the free base: eidem, US 4197241 (1980 to Wyeth). Properties: P. G. Goode, A. C. White, Br. J. Pharmacol. 43, 462 (1971). HPLC determn in plasma: T. Frost, Analyst 106, 999 (1981). Clinical pharmacokinetics: G. Davies, Eur. J. Clin. Pharmacol. 23, 535 (1982). Pharmacology and abuse potential: R. E. Johnson, D. R. Jasinski, Clin. Pharmacol. Ther. 41, 426 (1987). Symposium on clinical studies: Postgrad. Med. J. 59, Suppl. 1, 1-94 (1983). Review of pharmacology and clinical efficacy: B. Holmes, A. Ward, Drugs 30, 285-312 (1985).

Chemical structure

Properties

Cryst from acetonitrile, mp 127.5-133°.

Derivative

Hydrochloride.

Nomenclature

CAS number: 59263-76-2
Wy-22811; Meptid (Wyeth).
C15H23NO.HCl; mol wt 269.81.
C 66.77%, H 8.97%, N 5.19%, O 5.93%, Cl 13.14%.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids