6727. Nupharidine

Nomenclature

CAS number: 468-89-3
[1R-(1α,4β,5α,7β,9aα)]-4-(3-Furanyl)octahydro-1,7-dimethyl-2H-quinolizine 5-oxide.
C15H23NO2; mol wt 249.35.
C 72.25%, H 9.30%, N 5.62%, O 12.83%.

Description and references

From rhizome of Nuphar luteum (L.) Sibth. & Sm. (Nymphaea lutea L.), Nymphaeaceae: Goris, Crété, Bull. Sci. Pharmacol. 17, 13 (1910). Isoln from N. japonicum DC., Nymphaeaceae and structure: Kotake et al., Ann. 606, 148 (1957). Total synthesis: Kotake et al., Bull. Chem. Soc. Jpn. 35, 698 (1962). Abs configuration: Kawasaki et al., ibid. 41, 1264 (1968); La Londe et al., J. Am. Chem. Soc. 93, 2501 (1971). Determn of crystal structure, abs config and stereochemistry by x-ray diffraction methods: J. Ohrt et al., J. Cryst. Mol. Struct. 3, 3 (1973).

Chemical structure

Properties

Crystals, mp 221°. [α]D +15°. Soluble in alcohol, chloroform, ether, acetone, amyl alcohol, dil acids. The base is tasteless, the salts bitter.