Mitragyna speciosa alkaloids

Methoxy-3,4,5,6-tetradehydrocorynantheol (286), 3,4,5,6,18,19-Hexade-hydroochropposinine (287), 3,4,5,6-Tetradehydrositsirikine (288), Alstonine (289), the no-name-alkaloid (290) (Mitragyna speciosa) (98T8433), 3,4,5,6-Tetradehydropalicoside (291) and its methylester which were isolated recently from Strychnos mellodora (99P1171), Serpentine (292), and Serpentinine (293) are known representatives of this class of alkaloids. 

Epiallo Series. Previously, only speciociliatine (63) was known as a cory-nantheine-type alkaloid having an epiallo skeleton. Two new alkaloids in this series were isolated during the last decade, i.e., epiallocorynantheine (64) from Uncaria attenuata (59) and 3-isocorynantheidine (65) from Mitragyna speciosa Korth. (58). 

Horie, S., Koyama, F., Takayama, H., Ishikawa, H., Aimi, N., Ponglux, D., Matsumoto, K. and Murayama, T. 2005. Indole alkaloids of a Thai medicinal herb, Mitragyna speciosa, that has opioid agonistic effect in ginea-pig ileum. Planta Medica, 71 231-236. 

Chemistry and pharmacology of analgesic indole alkaloids from the Rubiaceous plant, Mitragyna speciosa 04CPB916. 

From a South-East Asian plant Mitragyna speciosa. Related to the coffee plant. Alkaloids include mitragynine similar to ibogaine. Euphoria, vomiting, vertigo, arrhythmias, twitching. The dried leaf is called Kratom and is smoked, the distillate is called Mambog and is imbibed. 

Chemical studies on the analgesic indole alkaloids from the traditional medicine (Mitragyna speciosa) used for opium substitute 00YZ959. 

Specionoxeine (mp 225°) and isospecionoxeine (mp 179°) are two isomeric oxindole alkaloids of C23H2SN2O5 constitution isolated from Mitragyna speciosa (27). The similarity of their spectral data and those of other oxindoles indicates that the two alkaloids possess a rhyncho-phylline-type structure and carry an extra methoxyl group on the aromatic ring. 

Ali Z, Demiray H, Khan LA. Isolation, characterization, and NMR spectroscopic data of indole and oxindole alkaloids from Mitragyna speciosa. Tetrahedron Lett 2014 55 (2) 369-72. 

Alkaloid front bark of Mitragyna speciosa, Korthals. Monoclinic platelets from EtOH. M.p. 244r-5°. Sol. MegCO, C.H,. Mod. sol. Et. [a] - 59-15° in CHCls. 

Rubiaceous Alkaloids e.g.. Cinchona Sp. (Quinine), Mitragyna speciosa Korth (Katum, Kratum, Kutum), Pausinystalia johimbe (K. Schum) (Y ohimbe)... 

The indole alkaloids of Mitragyna hirsuta Havil, M.javanica Koord. et Val. var. microphylla Craib, M. speciosa, and Nauclea coadunata are mostly in the corynantheine-heteroyohimbine-yohimbine group. The alkaloids isolated from the leaves of Mitragyna hirsuta have been identified as hirsutine, rhynchophylline, isorhynchophylline, mitraphylline, isomi-... 

The occurrence of alkaloids in Mitragyna species was first reported by Hooper, who isolated a crystalline alkaloid in 0.15% yield from the leaves of M. parvifolia (1) this alkaloid was not named and has not since been reinvestigated. The leaves of M. speciosa contain the amorphous alkaloid mitragynine, mp 105°-115° (2, 3), while the bark contains mitraspecine, C23H30N2O5, mp 244°-245°, [a]ff° -59.15° (4, 5). A third base, giving an amorphous picrate, mp 123°-127°, is also present, but this has not been studied further, since no crystalline derivatives could be obtained (6). The alkaloid mitraphylline, C21H24N2O4, mp 270°,... 

Continuing their investigations in this series the Chelsea group have reexamined the bases present in the leaves of M. speciosa Korth. and have isolated ten alkaloids, of which mitragynine (V R == OMe), now obtained crystalline for the first time (as its solvate with ethanol) (7-9), and speciofoline (stereoisomer of I) (10), have been reported earlier. Other known alkaloids include corynantheidine (V R = H) and ajmali-cine (VI), neither of which has previously been encountered in Mitragyna species, mitraphylline (VII), and isomitraphylline (VIII) (8, 9, 11). The four new bases obtained are speciophylline, C21H24N2O4 (mp 183° ... 

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