Structural Formula Vector Image
Title: Nalorphine
CAS Registry Number: 62-67-9
CAS Name: (5a,6a)-7,8-Didehydro-4,5-epoxy-17-(2-propenyl)morphinan-3,6-diol
Additional Names: N-allylnormorphine; allorphine; antorphine; NANM
Molecular Formula: C19H21NO3
Molecular Weight: 311.37
Percent Composition: C 73.29%, H 6.80%, N 4.50%, O 15.42%
Literature References: Prepd from normorphine: McCawley et al., J. Am. Chem. Soc. 63, 314 (1941); amended procedure: Hart, McCawley, J. Pharmacol. 82, 339 (1944); Weijlard, Erickson, J. Am. Chem. Soc. 64, 869 (1942); US 2364833 (1944); Weijlard, US 2891954 (1959 to Merck & Co.). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Comprehensive description: M. U. Zubair et al., Anal. Profiles Drug Subs. 18, 195-219 (1989).
Properties: Crystals from ether, mp 208-209° (not 92-93° as first given by McCawley). [a]D25 -155.3° (c = 3 in methanol). Sparingly sol in water, ether. Sol in alc, acetone, chloroform, dil alkalies. uv max (in acid): 285 nm; (in alkali): 298 nm.
Melting point: mp 208-209° (not 92-93° as first given by McCawley)
Optical Rotation: [a]D25 -155.3° (c = 3 in methanol)
Absorption maximum: uv max (in acid): 285 nm; (in alkali): 298 nm
Derivative Type: Hydrobromide
CAS Registry Number: 1041-90-3
Trademarks: Lethidrone (Burroughs Wellcome); Norfin (Lusofarmaco)
Molecular Formula: C19H21NO3.HBr
Molecular Weight: 392.29
Percent Composition: C 58.17%, H 5.65%, N 3.57%, O 12.24%, Br 20.37%
Properties: Crystals from alc, dec 258-259°. Sol in water.
Derivative Type: Hydrochloride
CAS Registry Number: 57-29-4
Trademarks: Nalline (Merck & Co.)
Molecular Formula: C19H21NO3.HCl
Molecular Weight: 347.84
Percent Composition: C 65.61%, H 6.37%, N 4.03%, O 13.80%, Cl 10.19%
Properties: Crystals from alc, mp 260-263°. Sol in water. Moderately sol in alc. uv max (water): 285 nm. IR and polarographic data: Seagers et al., J. Am. Pharm. Assoc. Sci. Ed. 41, 640 (1952). pH of 0.5% aq soln: 5.0. LD50 s.c. in rats: 1460 mg/kg (Goldenthal).
Melting point: mp 260-263°
Absorption maximum: uv max (water): 285 nm
Toxicity data: LD50 s.c. in rats: 1460 mg/kg (Goldenthal)
NOTE: This is a controlled substance: 21 CFR, 1308.13.
Therap-Cat: Narcotic antagonist.
Therap-Cat-Vet: Narcotic antagonist.
Keywords: Narcotic Antagonist.

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