ignavine

Description

This aconitine alkaloid is present in several A conitum species indigenous to Japan, e.g. Aconitum calliantum Koidzumi, A. grossedentatum, Nakai, A. hakusanense Nakai, A. kamtschaticum Willd. et Reichb., A. lucidusculum Nakai, A. senanense Nakai, A. subcuneatum Nakai, A. tortuosum Willd. and A. Zuccarini Nakai. It yields clusters of colourless needles when crystallized from Me2COMeOH and gives a form, m.p. 172-4 °c in addition to the one having the above melting point. It is dextrorotatory with [α]²⁹_D~} + 85.27° (MeOH), or [α]¹⁴_D + 92.98°. Crystalline salts of the alkaloid have been prepared, e.g. the hydrochloride, m.p. 245-6°C (dec.); hydrobromide, m.p. 260-2°C (dec.) and the nitrate which crystallizes as the monohydrate, m.p. 220-2°C (dec. dry). Alkaline hydrolysis furnishes benzoic acid and hydroignavinol, C20H2S04N, m.p. 302°C.

References

Ochiai et al., J. Pharm. Soc., Japan, 72, 816 (1952) Ochiai et al., ibid, 76, 550 (1956) Ochiai", Okamoto, Sasaki., ibid, 75,545 (1955) Ochiai et al., Chem. Pharm. Bull., 6,327 (1958) Ochiai et al., ibid, 8, 976 (1960) Pelletier., Tetrahedron, 14,103 (1961)