Hydromorphone
Title: Hydromorphone
CAS Registry Number: 466-99-9
CAS Name: 4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-one
Additional Names: dihydromorphinone
Trademarks: Dimorphone; Novolaudon
Molecular Formula: C17H19NO3
Molecular Weight: 285.34
Percent Composition: C 71.56%, H 6.71%, N 4.91%, O 16.82%
Literature References: Prepn by electrolytic reduction of morphine: Takagi, Ueda, J. Pharm. Soc. Jpn. 56, 44 (1936); Nakamura, ibid. 62, 347 (1942); by oxidation of dihydromorphine: Rapoport et al., J. Org. Chem. 15, 1103 (1950); Homeyer, De la Mater, US 2628962 and US 2654756 (both 1953 to Mallinckrodt); Rapoport, US 2649454 (1953 to Univ. of California). Crystal structure: Steinmetz, Z. Kristallogr. 67, 434 (1928). Toxicity data: M. E. Buchwald, G. S. Eadie, J. Pharmacol. Exp. Ther. 71, 197 (1941). Review: King et al., U.S. Public Health Reports Suppl. no. 113, 38 pp (1935).
Properties: Crystals from ethanol, mp 266-267°. [a]D25 -194° (c = 0.98 in dioxane).
Melting point: mp 266-267°
Optical Rotation: [a]D25 -194° (c = 0.98 in dioxane)
 
Derivative Type: Hydrochloride
CAS Registry Number: 71-68-1
Trademarks: Dilaudid (Knoll); Laudicon; Hymorphan (Endo); Palladone (Napp)
Molecular Formula: C17H19NO3.HCl
Molecular Weight: 321.80
Percent Composition: C 63.45%, H 6.26%, N 4.35%, O 14.92%, Cl 11.02%
Properties: Crystals, dec 305-315° (evacuated tube). [a]D25 -133°. Sol in 3 parts water; sparingly sol in alc. LD50 in mice (mg/kg): 61-96 i.v. (Buchwald, Eadie).
Optical Rotation: [a]D25 -133°
Toxicity data: LD50 in mice (mg/kg): 61-96 i.v. (Buchwald, Eadie)
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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