シノメニン

解説C19H23NO4(329.40)．シノメニンは，ツヅラフジ科オオツヅラフジSinomenium acutumの根茎に含まれるモルヒネ型アルカロイド．無色の針状晶．融点161 ℃．[α]D"－71°(エタノール)．エタノール，アセトン，クロロホルムに可溶，水，エーテル，ベンゼンに難溶．立体的にはモルヒネと対称の絶対配置をもっている．LD50 580 mg/kg(マウス，経口)．森北出版「化学辞典（第2版）

説明Isolated by Ohta from Cocculus diversifolius DC., this alkaloid forms colourless crystals from MeOH. It is stated to possess a powerful reflex action and to be aspasm stimulant, finally causing paralysis and death in toxic doses. It is also said to suppress the hypotensive action of dihydroxyphenylethanolethylamine.

来歴The chemical structure of sinomenine is composed of four rings, A, B, C, and D, similar to the structure of morphine. Ring A is a benzene ring, and ring B is a half-chair-shaped, six-member ring. The C ring is a twisted-chair-type, sixmember ring that has an a, β-unsaturated ketone structure attached to the B ring. The D ring is a nitrogen-containing, sixmember ring under the B ring. Its structure is shown below; the current structural modification of sinomenine is mainly focused on the A/C active group. Based on the transformation of the A ring, it was found that the 1-substituted formyl derivative of sinomenine showed the strongest inhibitory effect on the inflammatory response of the mouse ear. The 4-substituted p-chlorobenzoyl-sinomenine has the strongest anti-inflammatory and analgesic activity. The biotransformation and chemical synthesis were also used to prepare the di-sinomenine derivatives linked by carbon and carbon, which was stronger than that of sinomenine and had a strong inhibitory effect on cell inflammatory factors. Sinomenine derivatives of the C ring with a pyrazine ring have a strong inhibitory effect on T, B lymphocyte proliferation reaction, which can be used for the preparation of immunomodulatory drugs. The transformation of C ring carbonyl yielded a series of shift alkali derivatives, with strong anti-inflammatory and analgesic effects. These attempts are important for the development of new drugs.

使用weak abortifacient, immunosuppressant, analgesic, antiinflammatory; LD50 (po) 580 mg/kg; (ip) 285 mg/kg(mouse)

純化方法Crystallise the salt from water (1g/1.5mL) or EtOH. The free base [115-53-7] M 329.4, has m 161o (from EtOH) (and again at 182o) after crystallisation from *C6H6, and [] D -78.9o (c 1, EtOH). The picrate has m 159-162o(dec) (from H2O). [Beilstein 21 II 470, 21 III/IV 6670.]