サマンダリン

解説C19H31NO2(346.33)．ヨーロッパ産サンショウウオの一種Salamander maculosaの皮脂腺から分泌される有毒性アルカロイド．構造上，ステロイドアルカロイドに属する．融点188 ℃．[α]D"＋43°(アセトン)．1匹より4～24 mg が得られる．サマンダリンは主アルカロイドで，ほかにサマンダロン(C19H29NO2，融点190 ℃)，サマンダリジン(C21H31NO3，融点290 ℃)，シクロネオサマンジオン(C19H29NO2，融点119 ℃)などが分離されており，サマンダリン系アルカロイドと総称する．LD50 1 mg/kg(ウサギ，皮下)．森北出版「化学辞典（第2版）

説明This pentacyclic alkaloid also occurs in the skin secretion of Salamandra species, particularly S. atra and S. maculosa. It forms colourless crystals from a variety of solvents but when crystallized from MeOH contains solvent of crystallization. The solutions are strongly alkaline and the base is dextrorotatory with [α]17D + 43.7°. Two bridge methyl groups, a non-phenolic hydroxyl group and a methylimino group are present in the molecule. Several crystalline derivatives have been prepared including the hydrochloride, m.p. 32l-2°C; the O,N-diacetyl derivative, m.p. l67-8°C; the monoformyl compound, m.p. l48-ISOoC; diformyl derivative, m.p. 2S6-g0C; N-nitroso compound, m.p. 164-5°C and the N-methyl derivative which is characterized as the hydrochloride, m.p. 300-2°C (dec.) and the methiodide, m.p. 27l-2°C.