6275. Morphinan

Nomenclature

CAS number: 468-10-0
[4aR(4aα,10α,10aα)]-1,3,4,9,10,10a-Hexahydro-2H-10,4a-(iminoethano)phenanthrene; 1,2,3,9,10,10a-hexahydro-10,4a(4H)-iminoethanophenanthrene.
C16H21N; mol wt 227.34.
C 84.53%, H 9.31%, N 6.16%.

Description and references

Parent substance of the morphine alkaloids, codeine, thebaine, etc. Prepd from 1-benzyl-1,2,3,4,5,6,7,8-octahydro-2-methylisoquinoline: Grewe, Mondon, Ber. 81, 279 (1948); from β-cyclohexenyl-N-phenacetylethylamine: Grewe et al., Ber. 84, 527 (1951).

Chemical structure

Properties

Oily liq, bp0.05 115°.

Derivative

Hydrochloride.

Properties

Crystals from acetone + ether, dec 229°.

Derivative

Sulfate.

Properties

Crystals from alcohol + ether, dec 195°.

Derivative

N-Methylmorphinan.

Properties

Crystals, mp 61°.