ROEMERINE (Rernerine)

Description

An aporphine alkaloid, this base is present in Cryptocarya angulata, Nelurnbo nucifera and Roerneria refracta. It is laevorotatory with [α]_D - 77.18° (EtOH) and forms crystalline salts and derivatives of which the following have been prepared: the hydrochloride, m.p. 262-3°C; hydriodide, m.p. 24SoC; picrate, m.p. 19S-6°C and the methiodide, m.p. 2lS-6°C. The end product of the Hofmann degradation of the methiodide is a methylenedioxyphenanthrene, m.p. 84-SoC giving a picrate, m.p. l67-8°C. The structure, as S:6-methylenedioxyN-methylaporphine, has been confirmed by synthesis. The (-)-roemerine, produced synthetically, is dimorphic with m.p. 8S-7°C and 102°C and has a specific rotation of [α]_D - 79.9° (EtOH).

References

Konovalova, Yunusov, Orekhov.,J. Gen. Chern. USSR, 9, 1868 (1939)
Konovalova, Yunusov, Orekhov., Bull. Soc. Chirn. Fr., 6, 1479 (1939)
Konovalova, Yunusov, Orekhov., ibid, 7, 70 (1940)
Marion, Grassie.,J. Arner. Chern. Soc., 66, 1290 (1944)
Cooke, Haynes., Austral. J. Chern., 7,99 (19S4)
Tomita et al., J. Pharrn. Soc., Japan, 81,469, 1202 (1961)