2956. Dezocine

Nomenclature

CAS number: 53648-55-8
(5R,11S,13S)-13-Amino-5,6,7,8,9,10,11,12-octahydro-5-methyl-5,11-methanobenzocyclodecen-3-ol; Wy-16225; Dalgan (Wyeth).
C16H23NO; mol wt 245.36.
C 78.32%, H 9.45%, N 5.71%, O 6.52%.

Description and references

Synthetic opioid agonist-antagonist. Prepn: M. E. Freed et al., DE 2159324 (1972 to Am. Home Products), C.A. 79, 53094w (1973); eidem, J. Med. Chem. 16, 595 (1973). Pharmacology: J. L. Malis et al., J. Pharmacol. Exp. Ther. 194, 488 (1975). Metabolism: S. F. Sisenwine, C. O. Tio, Drug Metab. Dispos. 9, 37 (1981). Pharmacokinetics: S. F. Sisenwine et al., ibid. 10, 366 (1982). Clinical studies: W. Oosterlinck, A. Verbaeys, Curr. Med. Res. Opin. 6, 472 (1980); J. W. Downing et al., Br. J. Anaesth. 53, 59 (1981).

Chemical structure

Derivative

Hydrobromide salt.
C15H23NO.HBr; mol wt 314.26.
C 57.33%, H 7.70%, N 4.46%, O 5.09%, Br 25.43%.

Properties

Crystalline powder, mp 269-270°. pH (2% aq soln): 4.6. Soly in water: >20 mg/ml. LD50 in female mice, rats (mg/kg): 313, 232 orally; 129, 270 i.m. (Malis).

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids