Levorphanol
Title: Levorphanol
CAS Registry Number: 77-07-6
CAS Name: 17-Methylmorphinan-3-ol
Additional Names: (-)-3-hydroxy-N-methylmorphinan; levorphan; lemoran
Manufacturers' Codes: Ro-1-5431
Molecular Formula: C17H23NO
Molecular Weight: 257.37
Percent Composition: C 79.33%, H 9.01%, N 5.44%, O 6.22%
Literature References: Orally active synthetic morphine analog. Prepn of racemate from 2-methyl-1-benzyl-1,2,3,4,5,6,7,8-octahydroisoquinoline: Grewe, Naturwissenschaften 33, 333 (1946); Angew. Chem. A59, 198 (1947); Grewe, Mondon, Ber. 81, 279 (1948); CH 280674 (1952 to Hoffmann-La Roche), C.A. 47, 7554 (1953). Prepn of isomers: Schnider, Grüssner, Helv. Chim. Acta 34, 2211 (1951); Vogler, US 2744112 (1956 to Hoffmann-La Roche). Absolute configuration: Corrodi et al., Helv. Chim. Acta 42, 212 (1959). Analgesic activity and toxicity data: L. O. Randall, G. Lehmann, J. Pharmacol. Exp. Ther. 99, 163 (1950). HPLC determn in plasma: R. Lucek, R. Dixon, J. Chromatogr. 341, 239 (1985). Clinical pharmacokinetics: R. Dixon et al., Res. Commun. Chem. Pathol. Pharmacol. 41, 3 (1983).
Properties: Crystals, mp 198-199°. [a]D20 -56° (c = 3 in absolute alcohol).
Melting point: mp 198-199°
Optical Rotation: [a]D20 -56° (c = 3 in absolute alcohol)
 
Derivative Type: Tartrate dihydrate
CAS Registry Number: 5985-38-6
Manufacturers' Codes: Ro-1-5431/7
Trademarks: Dromoran (Roche); Levo-Dromoran
Molecular Formula: C17H23NO.C4H6O6.2H2O
Molecular Weight: 443.49
Percent Composition: C 56.87%, H 7.50%, N 3.16%, O 32.47%
Properties: Crystals, mp 113-115° (when anhydrous, mp 206-208°). [a]D20 -14° (c = 3 in water). pH of a 0.2% aq soln 3.4 to 4.0. One gram dissolves in 45 ml water, in 110 g alcohol, in 50 g ether.
Melting point: mp 113-115°; when anhydrous, mp 206-208°
Optical Rotation: [a]D20 -14° (c = 3 in water)
 
Derivative Type: dl-Form
CAS Registry Number: 297-90-5
Additional Names: Racemorphan; methorphinan
Properties: Crystals from anisole and dil alcohol, mp 251-253°.
Melting point: mp 251-253°
 
Derivative Type: dl-Form hydrobromide
CAS Registry Number: 5985-35-3
Manufacturers' Codes: Nu-2206
Molecular Formula: C17H23NO.HBr
Molecular Weight: 338.28
Percent Composition: C 60.36%, H 7.15%, N 4.14%, O 4.73%, Br 23.62%
Properties: Crystals, mp 193-195°. Sol in water; sparingly sol in alcohol. Practically insol in ether. LD50 i.v. in mice: 41 mg/kg (Randall, Lehmann).
Melting point: mp 193-195°
Toxicity data: LD50 i.v. in mice: 41 mg/kg (Randall, Lehmann)
 
Derivative Type: d-Form
CAS Registry Number: 125-73-5
Additional Names: Dextrorphan
Manufacturers' Codes: Ro-1-6794
Literature References: HPLC-MS/MS determn in urine: M. L. Constanzer et al., J. Chromatogr. B 816, 297 (2005).
Properties: Crystals, mp 198-199°. [a]D20 +56.3° (c = 3 in abs alcohol).
Melting point: mp 198-199°
Optical Rotation: [a]D20 +56.3° (c = 3 in abs alcohol)
 
Derivative Type: d-Form tartrate monohydrate
Molecular Formula: C17H23NO.C4H6O6.H2O
Molecular Weight: 425.47
Percent Composition: C 59.28%, H 7.34%, N 3.29%, O 30.08%
Properties: Crystals, mp 183-185°. [a]D20 +34.6° (c = 3 in water). Sol in water.
Melting point: mp 183-185°
Optical Rotation: [a]D20 +34.6° (c = 3 in water)
 
NOTE: Levorphanol and racemorphan are controlled substances (opiates): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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