Tsuduranine

Description

This aporphine alkaloid occurs with sinomenine in Sinomenium acutum Rehd. et Wils and was first isolated by Goto from the mother liquors following removal of the former base. The alkaloid is crystalline, softens at 105°C and melts at 125°C. When crystallized from EtOH it has the higher melting point given above. It is laevorotatory with [α]²⁰_D - 127.5° (EtOH) and is solu ble in most organic solvents and dilute alkalies. The sparingly soluble hydrochloride has m.p. 286°C (dec.); [α]^14.5_D - 148° (aqueous MeOH). A phenolic hydroxyl group and an imino group are present and yield a series of derivatives, e.g. the N-methyl methiodide, m.p. 224°C; N-acetyl derivative, m.p. 277°C; [α]¹⁸_D - 395.24° (MeOH-CHC13); O,N-diacetyl derivative, m.p. 170°C; [α]¹⁴_D - 321.7° (MeOH); G-methyl ether yielding the N-acetyl compound, m.p. 189°C and the O-ethyl compound which forms a hydrochloride, m.p. 234-6°C; hydrobromide, m.p. 246-8°C and an ethiodide, m.p. l86-7°C. When degraded by the Hofmann process, the alkaloid furnishes a trimethoxyvinylphenanthrene, m.p. 93-5°C.

Definition

ChEBI: Tuduranine is an aporphine alkaloid.

References

Goto.,Annalen, 521,175(1935)
Goto, Shishido., ibid, 539,262 (1939)
Goto, Shishido., Proc. Imp. Acad. Tokyo, 15, 8 (1939)
Goto, Yamamato., ibid, 29, 513 (1953)