1530. Butorphanol

Nomenclature

CAS number: 42408-82-2
17-(Cyclobutylmethyl)morphinan-3,14-diol; (-)-N-cyclobutylmethyl-3,14-dihydroxymorphinan; levo-BC-2627.
C21H29NO2; mol wt 327.46.
C 77.02%, H 8.93%, N 4.28%, O 9.77%.

Description and references

Mixed opioid agonist-antagonist. Prepn: I. Pachter et al., DE 2243961; eidem, US 3819635 (1973, 1974 to Bristol-Myers); I. Monkovic, T. Thomas, US 3775414 (1973 to Bristol-Myers). Total synthesis and pharmacology: I. Monkovic et al., J. Am. Chem. Soc. 95, 7910 (1973); eidem, Can. J. Chem. 53, 3094 (1975). Clinical study: F. Vargas-Arreola et al., Curr. Ther. Res. 22, 186 (1977). Antitussive effect: R. L. Cavanaugh et al., Arch. Int. Pharmacodyn. Ther. 220, 258 (1976). Review: R. C. Heel et al., Drugs 16, 473-505 (1978); F. S. Caruso et al., in Pharmacological and Biochemical Properties of Drug Substances vol. 2, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1979) pp 19-57.

Chemical structure

Properties

Solid, mp 215-217°. [α]D -70.0° (c = 0.1 in methanol).

Derivative

Tartrate.

Nomenclature

CAS number: 58786-99-5
Stadol (BMS); Torbugesic (Fort Dodge); Torbutrol (BMS).
C21H29NO2.C4H6O6; mol wt 477.55.
C 62.88%, H 7.39%, N 2.93%, O 26.80%.

Properties

White powder. mp 217-219°. [α]D22 -64.0° (c = 0.4 in methanol). Sparingly sol in water; slightly sol in methanol; sol in dilute acids. Insol in ethanol, chloroform, ethyl acetate, ethyl ether, hexane. LD50 in mice, rats (mg/kg): 40-57, 17-20 i.v.; 395-527, 570-756 orally (Heel).

Note

This is a controlled substance: 21 CFR, 1308.14.

Therapeutic Category

Analgesic.

Therapeutic Category (Veterinary)

Analgesic; antitussive.

Keywords

Analgesic; Opioids; Morphinan Derivatives