6707. Norlevorphanol

Nomenclature

CAS number: 1531-12-0
Morphinan-3-ol; (-)-3-hydroxymorphinan; (-)-1,3,4,9,10,10a-hexahydro-6-hydroxy-2H-10,4a-iminoethanophenanthrene; NIH-7539.
C16H21NO; mol wt 243.34.
C 78.97%, H 8.70%, N 5.76%, O 6.57%.

Description and references

Opioid analgesic. Prepn of (-) and (+) isomers: O. Schnider, A. Grüssner, Helv. Chim. Acta 34, 2211 (1951); J. Hellerbach, et al., ibid. 39, 429 (1956); GB 765920 (1957 to Hoffmann-La Roche).

Chemical structure

Properties

Crystals from acetone + methanol, mp 270-272°. [α]D21 -42 ±2° (c = 1 in methanol).

Derivative

Hydrobromide.

Nomenclature

CAS number: 63732-85-4
C16H21NO.HBr; mol wt 324.26.
C 59.26%, H 6.84%, N 4.32%, O 4.93%, Br 24.64%.

Properties

Crystals from water, mp 222-224°.

Derivative

(+)-Form.

Nomenclature

CAS number: 15676-23-0
(9α,13α,14α)-Morphinan-3-ol; nordextrorphan.

Description and references

Secondary metabolite of dextromethorphan, q.v.: G. Pfaff et al., Int. J. Pharm. 14, 173 (1983). Stereocontrolled synthesis: Y. Génisson et al., J. Org. Chem. 58, 2052 (1993).

Properties

Crystals from acetone, mp 258-259°. [α]D +40° (c = 0.5 in methanol).

Note

Norlevorphanol is a controlled substance (opiate): 21 CFR, 1308.11.

Use

Intermediate in synthesis of morphinan derivatives.