13-02338. Ciramadol [Archived]

Nomenclature

CAS number: 63269-31-8
3-[(R)-(Dimethylamino)[(1R,2R)-2-hydroxycyclohexyl]methyl]phenol; ()-cis-2-(α-dimethylamino-m-hydroxybenzyl)cyclohexanol; Wy-15705.
C15H23NO2; mol wt 249.35.
C 72.25%, H 9.30%, N 5.62%, O 12.83%.

Description and references

Analgesic with narcotic agonist-antagonist properties. Prepn: J. P. Yardley, P. B. Russel, DE 2317183; eidem, US 3928626, US 4017637 (1973, 1975 and 1977 all to Am. Home). Synthesis, relative stereochemistry, biological activity: J. P. Yardley et al., Experientia 34, 1124 (1978). Abs config: W. Stallings, Jr., J. Donohue, J. Cryst. Mol. Struct. 11, 59 (1981). Determn in pharmaceutical dosage forms: H. K. Chan, A. G. Fogg, Anal. Chim. Acta 105, 423 (1979). Metabolism: C. O. Tio et al., Fed. Proc. 38, 2717 (1979). Respiratory effects in man: H. P. Wuest, Arch. Int. Pharmacodyn. Ther. 240, 45 (1979). Analgesic effect in chronic pain: M. J. Staquet, Curr. Med. Res. Opin. 6, 475 (1980).

Chemical structure

Properties

Cryst from acetone/hexane, mp 191-193°. [α]D25 46.92° (c = 1.061 in methanol).

Derivative

Hydrochloride.

Nomenclature

CAS number: 63323-46-6
Ciradol (Wyeth).
C15H23NO2.HCl; mol wt 285.81.
C 63.04%, H 8.46%, N 4.90%, O 11.20%, Cl 12.40%.

Properties

Cryst from acetone/methanol, mp 255-257° (effervescence). [α]D25 15.31° (c = 1.067 in methanol).

Therapeutic Category

Analgesic.

Keywords

Analgesic (Non-Narcotic)

Status

This monograph has been retired and is no longer subject to revision or update.