ROTUNDIFOLINE (Stipulatine)

Description

This alkaloid from Mitragyna rotundifolia and M. rubrostipulata, is isomeric with Mitragynol (q.v.) and is obtained as colourless prisms from MeOH. It has [α]¹⁵_D + 124° (CHCI 3) and is readily soluble in CHCI3, moderately so in EtOH, Me2CO or C6H6 and only sparingly soluble in Et20 or AcOEt. The ultraviolet spectrum has absorption maxima at 222 and 292 ffi/J.. Several crystalline salts and derivatives have been prepared including the hydrochloride, m.p. 222°C; hydrobromide, m.p. 217°C; perchlorate, m.p. 280°C; platinichloride, m.p. 232-4°C (dec.); the N-methyl derivative, m.p. 77-9°C and the N-acetyl compound, m.p. 170-1°C. The base also forms an additional compound with trinitrobenzene having m.p. 196°C. The structure of the alkaloid has been established by spectroscopic techniques.

References

Barger, Dyer, Sargent.,J. Org. Chem., 4,418 (1939)
Badger, Cook, Ongley.,J. Chem. Soc., 867 (1950)
Hendrickson., Chem. & Ind., 713 (1961)
Beckett, Tackie., ibid, q 22 (1963)
Badger et al., Proc. Chem. Soc., 206 (1963)
Hendrickson, Sims., Tetrahedron Lett., 929 (1963)
Beckett, Lee, Tackie., ibid, 1709 (1963)