9800. Tsuduranine

Nomenclature

CAS number: 517-97-5
(6aR)-5,6,6a,7-Tetrahydro-1,2-dimethoxy-4H-dibenzo[de,g]quinolin-10-ol; 1,2-dimethoxy-6aβ-noraporphin-10-ol; tuduranine.
C18H19NO3; mol wt 297.35.
C 72.71%, H 6.44%, N 4.71%, O 16.14%.

Description and references

In sinomenine mother liquors. Isoln: Got^o, Ann. 521, 175 (1935). Structure: Got^o, Shishido, Ann. 539, 262 (1939). Synthesis of dl-form: Narayanaswami et al., Indian J. Chem. 7, 945 (1969).

Chemical structure

Properties

Difficult to crystallize. Minute needles from slowly evaporating ether, mp about 125° (softens at 105°), or 204° depending on cryst form. [α]D20 -127.5° (c = 0.855 in ethanol). Freely sol in the usual organic solvents.

Derivative

Hydrochloride.

Properties

Shiny scales from water, dec 286°. [α]D15 -148° (c = 0.88 in water + methanol). Sparingly sol in water.