MAGNOLINE

Description

A closely-related bisbenzylisoquinoline base found also in Magnolia fuscata, the alkaloid occurs mainly in the leaves and is obtained in the pure form as a microcrystalline powder from EtOH or C6H6. It may be separated from magnolamine by virtue of its insolubility in hot C6H6. It is only sparingly soluble in most organic solvents but dissolves readily in aqueous alkalies. The alkaloid is laevorotatory with [α]_D - 9.6° (pyridine). It furnishes vitreous salts with mineral acids but yields a crystalline picrate as a yellow microcrystalline powder from EtOH, m.p. 160-2°C (dec.) and a picrolonate, m.p. 190°C (dec.). Treatment with CH2N2 gives the trimethyl ether, m.p. 1 09-1 10°C, oxidized by KMn04 in Me2CO to 2-methoxy-5:4'-dicarboxydiphenyl ether and a lactam, l-keto-6:7- dimethoxy-2-methyltetrahydroisoquinoline. On the basis of these results, the alkaloid may be represented by the above structure which makes it a close relative of dauricine (q.v.). The Ullmann reaction has been used by Kametani and his colleagues to synthesize the alkaloid.

Definition

ChEBI: Berbamunine is a benzyltetrahydroisoquinoline, a bisbenzylisoquinoline alkaloid and an isoquinolinol. It is a conjugate base of a berbamuninium(2+).

References

Pyman., J. Chern. Soc., 95, 1272 (1909) Proskurnina, Orekhov., Bull. Soc. Chirn., 5, 1357 (1958) Proskurnina, Orekhov., J. Gen. Chern. USSR., 10, 707 (1940) Synthesis: Kametani, !ida, Sakurai., Chern. Pharrn. Bull. (Tokyo), 16, 1623 (1968)