RHYNCOPHYLLINE (Mitrinermine)

Description

This alkaloid has been found in Mitragyna inermis Kuntze (Syn. M. african a Korth), M. rotundifolia (Roxb.) Kuntze (Syn. M. diversifolia Hook), M. stipulosa Kuntze (Syn. M. macrophylla Hiern) and also in Ourouparia guianensis and O. rhyncophylla Mats. The base yields colourless crystals from Me2CO and has [α]¹⁵_D - 14.5° (CHCI 3 ). The alkaloid is monoacidic and forms an N-acetyl derivative, m.p. 151-3° C; [α]²⁶_D - 7.6°. On hydrolysis with alkali, the base furnishes rhyncophyllic acid, C21H2604N2 which decomposes slowly above 150° C and may be methylated by CH2N 2 to form isorhyncophylline. The latter gives rhyncophylline and the N-acetylrhyncophylline on boiling with acetic anhydride.

References

Raymond-Hamet, Millet., Compt. rend., 199,587 (1934)
Raymond-Hamet, Millet., Compt. rend. soc. bioI., 116,1337 (1934)
Raymond-Hamet, Millet., Chem. Zentr., 1,3937 (1935)
Kondo et al., J. Pharm. Soc., Japan, 57, 237 (1937)
Barger, Dyer, Sargent.,J. Org. Chem., 4,418 (1939)
Seaton, Marion., Can. J. Chem., 35, 1102 (1957)
Wolfrom, Shafizadah, Armstrong., J. Amer. Chem. Soc., 80,4885 (1958)
Hendrickson., ibid, 84, 650 (1962)
Finch, Taylor., ibid, 84, 3871 (1962)
Collins, Overend., Chem. & Ind., 375 (1963)