다우리신

다우리신
다우리신 구조식 이미지
카스 번호:
524-17-4
한글명:
다우리신
동의어(한글):
다우리신
상품명:
DAURICINE
동의어(영문):
dauricine (8ci);auricine;Dauricine;(r-(r*,r*))-y);Menispermi Rhizoma。;Dauricinemenisperine;Menispermi Rhizoma P.E;North Bean Root Extract;Rhizoma menispermi extract;6,6'-Di-O-Methyldauricoline
CBNumber:
CB0499738
분자식:
C38H44N2O6
포뮬러 무게:
624.77
MOL 파일:
524-17-4.mol

다우리신 속성

녹는점
115°
알파
D11 -139° in methanol
끓는 점
712.3±60.0 °C(Predicted)
밀도
1.185±0.06 g/cm3(Predicted)
저장 조건
-20°C Freezer, Under inert atmosphere
용해도
DMSO(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
고체
물리적 상태
단단한 모양
산도 계수 (pKa)
9.31±0.45(Predicted)
색상
페일베이지
수용성
물에 약간 용해됨
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 데이터베이스
524-17-4
안전
  • 위험 및 안전 성명
  • 위험 및 사전주의 사항 (GHS)
그림문자(GHS): GHS hazard pictograms
신호 어: Warning
유해·위험 문구:
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드
H302 삼키면 유해함 급성 독성 물질 - 경구 구분 4 경고 GHS hazard pictograms P264, P270, P301+P312, P330, P501
H315 피부에 자극을 일으킴 피부부식성 또는 자극성물질 구분 2 경고 GHS hazard pictograms P264, P280, P302+P352, P321,P332+P313, P362
H319 눈에 심한 자극을 일으킴 심한 눈 손상 또는 자극성 물질 구분 2A 경고 GHS hazard pictograms P264, P280, P305+P351+P338,P337+P313P
H335 호흡 자극성을 일으킬 수 있음 특정 표적장기 독성 - 1회 노출;호흡기계 자극 구분 3 경고 GHS hazard pictograms
예방조치문구:
P261 분진·흄·가스·미스트·증기·...·스프레이의 흡입을 피하시오.
P264 취급 후에는 손을 철저히 씻으시오.
P264 취급 후에는 손을 철저히 씻으시오.
P270 이 제품을 사용할 때에는 먹거나, 마시거나 흡연하지 마시오.
P271 옥외 또는 환기가 잘 되는 곳에서만 취급하시오.
P280 보호장갑/보호의/보안경/안면보호구를 착용하시오.
P301+P312 삼켜서 불편함을 느끼면 의료기관(의사)의 진찰을 받으시오.
P302+P352 피부에 묻으면 다량의 물로 씻으시오.
P304+P340 흡입하면 신선한 공기가 있는 곳으로 옮기고 호흡하기 쉬운 자세로 안정을 취하시오.
P305+P351+P338 눈에 묻으면 몇 분간 물로 조심해서 씻으시오. 가능하면 콘택트렌즈를 제거하시오. 계속 씻으시오.
P330 입을 씻어내시오.
P332+P313 피부 자극이 생기면 의학적인 조치· 조언을 구하시오.
P337+P313 눈에 대한 자극이 지속되면 의학적인 조치· 조언를 구하시오.
P362 오염된 의복을 벗고 세척 후에 재사용하기
P403+P233 용기는 환기가 잘 되는 곳에 단단히 밀폐하여 저장하시오.
P405 밀봉하여 저장하시오.
P501 ...에 내용물 / 용기를 폐기 하시오.

다우리신 C화학적 특성, 용도, 생산

개요

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.

물리적 성질

Appearance: yellowish-white powder or crystal. Solubility: soluble in ethanol, methanol, chloroform, acetone, benzene and slightly soluble in ether. Density: 1.185 g/cm3. Melting point: 115 °C. Boiling point: 712.3 °C at 760 mmHg atmospheric pressure. Specific optical rotation: MeOH-139.

역사

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.

용도

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

Indications

Drugs whose main component is dauricine are still in clinical trials. Several formulations of dauricine have currently been developed, including tablets, capsules, injections, and so on. The main indications of dauricine in clinical trials are antiplatelet,antihypertensive and anti-arrhythmic.

정의

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).

Pharmacology

The main pharmacological actions of dauricine are as follows; Anti-arrhythmia: Dauricine can slow the heart rate and prolong conduction time in sinus rhythm, therefore reducing the incidence of arrhythmia.
Anti-myocardial ischemia: Dauricine has protective effect on myocardial ischemia and can improve hemodynamic disturbances during ischemia which is supposed to produce effect via mechanism of improving myocardial metabolism and anti-oxidation.
Anti-cerebral ischemia: Dauricine has an effective regulation on gene expression of Bcl-2 and Bax in cortical neurons after the ischemic brain injury, protecting against cerebral ischemia.
Anti-cerebral ischemia/reperfusion injury: Dauricine can inhibit apoptosis induced by cerebral ischemia/reperfusion injury by upregulating Bcl-2 expression and downregulating Bax expression. Also dauricine has the effect of anti-oxidation.
Antitumor activity: Dauricine can affect TGF-beta signaling pathway via upregulating gene expression of DPC4, and then the gene expression of P53 and P16 in tumor tissue, and finally reduce the gene expression of hFGF in tumor tissue. Thereby, the growth of various tumor cells could be inhibited.
The investigations of metabolism in vivo of dauricine indicate that it is rapidly and widely distributed in body and the drug concentration in organs is significantly higher than that in plasma, and this is possibly related to its strong lipid solubility and easy access to cells.

Clinical Use

No medicine in the market takes dauricine as the main component up till now. Many animal experiments and clinical studies suggest that dauricine can reverse the effect of MDR as verapamil. Since the clinical application of the classical drug verapamil is limited for the serious toxic side effects, the moderate pharmacological effect of dauricine has a vital clinical significance. The main side effect of dauricine by oral absorption is gastrointestinal reaction, such as diarrhea, nausea, abdominal distension, and so on. In addition, dauricine can accumulate in the body, leading to hepatorenal toxicity and central nervous system toxicity.

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