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]20D - 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]14.5D - 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]18D - 395.24°
(MeOH-CHC13); O,N-diacetyl derivative, m.p. 170°C; [α]14D - 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.
ChEBI: Tuduranine is an aporphine alkaloid.
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)
