Mitragynine

M. speciosa Korth. Mitragynine, mitraspecine and a base, or bases, giving an amorphous picrate, m.p. 123-7 . ... 

The most interesting product arising from more drastic degradation experiments is a base, C Hi ONa, m.p. 115-120°, obtained by distilling mitragynine with zinc dust. It contains a methoxyl and a methylimino group, and has a reactive methylene group, since it forms a p-nitrobenzyl-idene derivative, m.p. 255°. This base closely resembles both ind- and jM/r-iV-methylharmine, but is not identical with either. 

Miotic action by physostigmine and its substitutes, 549 miotine, 550 Mitragyna spp., alkaloids, 756 Mitragynine, 756, 757... 

Alio Series. Only two members of alio series of alkaloids are known cory-nantheidine (61) and mitragynine (62). No new alkaloid has been isolated since 1967. 

Mitragynine. Mitragynine (62) ethanedisulfonate exhibits analgesic and anti-tussive properties in animals (335). It has only weak respiratory depressant activity. 

Matsumoto, K., Yamamoto, L. T., Watanabe, K., Yano, S., Shan, J., Pang, J., Pang, P. K., Ponglux, D., Takayama, H. and Horie, S. 2005. Inhibitory effect of mitragynine, an analgestic alkaloid from Thai herbal medicine, on neurogenic contraction of the vas deferens. Life Sciences, 78 187-194. 

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°,... 

The pharmacology of these alkaloids has been discussed on numerous occasions (2, 3, 22, 23, 39-50). Mitragynine and, to a lesser extent, mitraphylline, exert a general depressant effect, and in some respects resemble cocaine (2, 3, 40, 44) mitraphylline is also a hypotensive (41). In connection with the use of Mitrogyna extracts as a febrifuge, it is of interest that rhynchophylline (mitrinermine) exhibits a significant antipyretic action (45, 46). The hypotensive effects of the total extracts (39) are, in part, owing to rhynchophylline (23). 

The UV-spectrum of mitragynine differs notably from the spectra of the other Mitragyna alkaloids. Whereas the absorption of the latter indicate the presence of oxindole nuclei, the spectrum of mitragynine shows a greater resemblance to that of the ajmalicine group of alkaloids (5). The presence of an indole nucleus is also suspected from its color reactions (2) and confirmed by the isolation of indole derivatives (so far unidentified) and 5-methoxy-9-methylharman (I) from the products of zinc dust distillation (6). The identification by synthesis (51) of this degradation product is of some interest, since the alkaloid itself does not apparently contain an iV-methyl group. Moreover, this was the first demonstration of the occurrence of a 4-hydroxyindole derivative in nature. 

Matrine (= Lupanindine) (quinolizidine) Mitragynine pseudoindoxyl (corynantheidine indole alkaloid)... 

Morphine and related morphinan alkaloids (A) akuammine, mitragynine (A), ibogaine and related indole alkaloids... 

---