5470. Levorphanol

Nomenclature

CAS number: 77-07-6
17-Methylmorphinan-3-ol; ()-3-hydroxy-N-methylmorphinan; levorphan; lemoran; Ro-1-5431.
C17H23NO; mol wt 257.37.
C 79.33%, H 9.01%, N 5.44%, O 6.22%.

Description and 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).

Chemical structure

Properties

Crystals, mp 198-199°. [α]D20 56° (c = 3 in absolute alcohol).

Derivative

Tartrate dihydrate.

Nomenclature

CAS number: 5985-38-6
Ro-1-5431/7; Dromoran (Roche); Levo-Dromoran.
C17H23NO.C4H6O6.2H2O; mol wt 443.49.
C 56.87%, H 7.50%, N 3.16%, O 32.47%.

Properties

Crystals, mp 113-115° (when anhydrous, mp 206-208°). [α]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.

Derivative

dl-Form.

Nomenclature

CAS number: 297-90-5
Racemorphan; methorphinan.

Properties

Crystals from anisole and dil alcohol, mp 251-253°.

Derivative

dl-Form hydrobromide.

Nomenclature

CAS number: 5985-35-3
Nu-2206.
C17H23NO.HBr; mol wt 338.28.
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).

Derivative

d-Form.

Nomenclature

CAS number: 125-73-5
Dextrorphan; Ro-1-6794.

Description and references

HPLC-MS/MS determn in urine: M. L. Constanzer et al., J. Chromatogr. B 816, 297 (2005).

Properties

Crystals, mp 198-199°. [α]D20 +56.3° (c = 3 in abs alcohol).

Derivative

d-Form tartrate monohydrate.
C17H23NO.C4H6O6.H2O; mol wt 425.47.
C 59.28%, H 7.34%, N 3.29%, O 30.08%.

Properties

Crystals, mp 183-185°. [α]D20 +34.6° (c = 3 in water). Sol in water.

Note

Levorphanol and racemorphan are controlled substances (opiates): 21 CFR, 1308.12.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Morphinan Derivatives