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4-[((1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル)メチル]-2-[4-[[(1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル]メチル]フェノキシ]フェノール

Dauricine

HCID 73400
ノート反応

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基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
524-17-4
標準SMILES
COc1cc2c(cc1OC)[C@@H](Cc1ccc(Oc3cc(C[C@@H]4c5cc(OC)c(OC)cc5CCN4C)ccc3O)cc1)N(C)CC2
InChIKey
AQASRZOCERRGBL-ROJLCIKYSA-N
分子式
C38H44N2O6
平均分子量
624.778 g/mol
単同位体質量
624.31993713

名称と識別子

優先名称
Dauricine
IUPAC
4-{[(1R)-6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2-(4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenoxy)phenol
現地名
4-[((1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル)メチル]-2-[4-[[(1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル]メチル]フェノキシ]フェノール
英語名
DAURICINE
分子式
C38H44N2O6
分子量
624.77

名称と別名

ダウリシン4-[((1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル)メチル]-2-[4-[[(1R)-1,2,3,4-テトラヒドロ-6,7-ジメトキシ-2-メチルイソキノリン-1-イル]メチル]フェノキシ]フェノール4-{[(1R)-6,7-ジメトキシ-2-メチル-1,2,3,4-テトラヒドロイソキノリン-1-イル]メチル}-2-(4-{[(1R)-6,7-ジメトキシ-2-メチル-1,2,3,4-テトラヒドロイソキノリン-1-イル]メチル}フェノキシ)フェノールdauricine (8ci)auricineDauricineDauricine-RM(r-(r*,r*))-y)Menispermi Rhizoma。DauricinemenisperineDauricine (Standard)Menispermi Rhizoma P.E
名称をさらに表示
North Bean Root Extract

データベース識別子

CAS
524-17-4
PubChem CID
73400
DTXSID
DTXSID90966808
ChEMBL
CHEMBL442717
ChEBI
CHEBI:4331
UNII
8QTO90G5W5
EC Number
683-103-9
Nikkaji
J8.642H

物性

物理化学的性質

融点
115 ° · 115°
比旋光度
11 · D11 -139° in methanol
沸点
712.3 · 712.3±60.0 °C(Predicted)
比重(密度)
1.185 · 1.185±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C Freezer, Under inert atmosphere
溶解性
DMSO(微量)、メタノール(微量)
外見
個体
酸解離定数(Pka)
9.31 · 9.31±0.45(Predicted)
色
ペールベージュ
水溶解度
slightly soluble in water
InChIKey
AQASRZOCERRGBL-ROJLCIKYSA-N
SMILES
C1(O)=CC=C(C[C@@H]2C3=C(C=C(OC)C(OC)=C3)CCN2C)C=C1OC1=CC=C(C[C@@H]2C3=C(C=C(OC)C(OC)=C3)CCN2C)C=C1
CAS データベース
524 · 524-17-4

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

安全データ

注意喚起語
警告
危険有害性情報
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H302

化学と産業

応用分野 · 3 件

説明Dauricine is a kind of phenolic aromatic compound which is isolated from Menispermaceae plants such as Asian Menispermum dauricum or Canadian Menispermum dauricum and can be classified as isoquinoline alkaloids. Rhizoma Menispermi is the dry rhizome of Menispermaceae plant Menispermum dauricum. Menispermum dauricum mainly distributes in the northern part of East Asia and is mainly distributed in the north, east and northeast regions of China. The usage of Rhizoma Menispermi as a kind of traditional Chinese medicine was firstly recorded in Kaibao Herbs with its function of detoxifying many drugs, relieving pains, reducing swelling and sore, curing fever and cough, and killing parasites. According to the Chinese Pharmacopoeia, Rhizoma Menispermi in the north of China is different from the herbs used in the south of China known as the same name. Based on the traditional Chinese Medicine theory, Rhizoma Menispermi has the feature of bitterness and coldness, with the meridian tropism in the lung, stomach, and intestine. The main effects of Rhizoma Menispermi are heat-clearing, detoxicating, wind-dispelling and pain-relieving according to its vital function lies in the therapy of swollen sore throat, enteritis diarrhea and rheumatic arthralgia. Alkaloid is the main chemical component of Rhizoma Menispermi, and besides dauricine, there are also other kinds of alkaloids such as dauriciline, O-methyldauricine, and daurisoline in it.

来歴Menispermum dauricum has been long used as a traditional Chinese medicine, but the research of its effective components has been slow. Dauricine was firstly separated and structure-confirmed by Fukuda Mayo using alumina column chromatography separation assay in 1964. At the same year, dauricine was first synthesized by two Japanese scientists, Tetsuji Tamayama and Rtani Rikazu, by means of Arndt-Eistert reaction and Bischler-Napieralski reaction. Thereafter, lots of scientists from various countries successively separated daurinoline, Menispermum Xinlin alkali, Menispermum succinylcholine alkali, chelilanthifoline, stepholidine, and many other monomeric components of Menispermum dauricum. The study of dauricine in China started from the Cultural Revolution Period. Under the guidance of integrated traditional Chinese and Western medicine, a large number of effective components in traditional Chinese herbs were extracted, separated and applied to clinic. Dauricine was firstly reported on the mainland as an active ingredient in herbs which can clear away heat and toxic materials. Moreover, dauricine was also used as an antineoplastic and muscle relaxant. There were many medicines whose principal component was dauricine had been under clinical research for its role of cardiovascular protection since the 1980s, most of these medicines were stagnating in phase II clinical trials.

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化合物ノート

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このページの内容基本情報名称と識別子物性安全と法規制化学と産業関連反応化合物ノート

使用Dauricine is a bisbenzylisoquinoline allkaloid derivative that displays a noted number of pharmaceutical properties. It is known to induces severe lung toxicity in animals.

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補足説明 · 1 件

定義ChEBI: A bisbenzylisoquinoline alkaloid resulting from the formal oxidative dimerisation of 4-{[(1R)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}phenol by attachment of the phenolic oxygen of one molecule to the benzene ring f the second (ortho to the phenolic hydroxy group of the latter).