2833. Dauricine

Nomenclature

CAS number: 524-17-4
4-[[(1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-2-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]phenol.
C38H44N2O6; mol wt 624.77.
C 73.05%, H 7.10%, N 4.48%, O 15.37%.

Description and references

From Menispermum dauricum DC., and M. canadense L., Menispermaceae: Kondo, Narita, J. Pharm. Soc. Japan no. 542, 279 (1927); C.A. 21, 2700 (1927); Manske, Can. J. Res. 21B, 17 (1943). Structure: Kondo et al., Ber. 68, 519 (1935); Kondo, Tomita, Arch. Pharm. 274, 65 (1936); Inubushi, Niwa, J. Pharm. Soc. Jpn. 72, 762 (1952); C.A. 47, 6430e (1953). Total synthesis: Kametani, Fukumoto, J. Chem. Soc. 1965, Suppl. 2, 6141.

Chemical structure

Properties

Slightly yellow amorphous base, mp 115°. [α]D11 -139° in methanol. Sol in alc, acetone, benzene; slightly sol in ether.

Derivative

Dimethiodide.
C38H44N2O6.2CH3I; mol wt 908.64.
C 52.87%, H 5.55%, N 3.08%, O 10.56%, I 27.93%.

Properties

Needles, mp 204°. [α]D20 -114°.