Butorphanol
Title: Butorphanol
CAS Registry Number: 42408-82-2
CAS Name: 17-(Cyclobutylmethyl)morphinan-3,14-diol
Additional Names: (-)-N-cyclobutylmethyl-3,14-dihydroxymorphinan
Manufacturers' Codes: levo-BC-2627
Molecular Formula: C21H29NO2
Molecular Weight: 327.46
Percent Composition: C 77.02%, H 8.93%, N 4.28%, O 9.77%
Literature 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.
Properties: Solid, mp 215-217°. [a]D -70.0° (c = 0.1 in methanol).
Melting point: mp 215-217°
Optical Rotation: [a]D -70.0° (c = 0.1 in methanol)
 
Derivative Type: Tartrate
CAS Registry Number: 58786-99-5
Trademarks: Stadol (BMS); Torbugesic (Fort Dodge); Torbutrol (BMS)
Molecular Formula: C21H29NO2.C4H6O6
Molecular Weight: 477.55
Percent Composition: C 62.88%, H 7.39%, N 2.93%, O 26.80%
Properties: Solid. mp 217-219°. [a]D22 -64.0° (c = 0.4 in methanol). LD50 in mice, rats (mg/kg): 40-57, 17-20 i.v.; 395-527, 570-756 orally (Heel).
Melting point: mp 217-219°
Optical Rotation: [a]D22 -64.0° (c = 0.4 in methanol)
Toxicity data: 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.
Therap-Cat: Analgesic (narcotic).
Therap-Cat-Vet: Analgesic (narcotic); antitussive.
Keywords: Analgesic (Narcotic).

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