4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6 -methyl-, (S)-

Description

This alkaloid, identified as the N-methyl derivative of laurotetanine (q. v.), has been isolated from Escholtzia californica Cham., Phylica fengerialla and P. rogersii Pillans. The base is known in two modifications; as an amorphous powder and a colourless crystals from MeOH containing 0.5 mole of solvent, identical with rogersine (q.v.). The alkaloid has [α]_D + 1110 (c 0.86, MeOH) and the ultraviolet spectrum in EtOH has absorption maxima at 219, 282 and 304 rn[J.; while that in alkaline solution (0.05 N/NaOH) has absorption maxima at 223 and 329 mil.
The alkaloid yields a crystalline hydriodide, m.p. 245°C; the methiodide, m.p. 199-2000 C and the Q-ethyl (-)-tartrate, m.p. 206-7°C (dec.) giving a methiodide, m.p. 213° C.

References

Arndt, Baarschers., J. Chern. Soc., 2244 (1964)
Manske, Shin., Can. J. Chern., 43,2180 (1965)
Baarschers, Arndt., Tetrahedron, 21,2155 (1965)
Pachler, Arndt, Baarschers., ibid, 21,2159 (1965)