DAURICINE CAS 524-17-4
Introduction：Basic information about DAURICINE CAS 524-17-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
DAURICINE Basic informationDescription References
| Product Name: | DAURICINE |
| Synonyms: | Asiatic Moonseed Root Extract;Menispermi Rhizoma。;-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenox;(r-(r*,r*))-y);4-[[(1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]-2-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl]methyl]phenoxy]phenol;4-[((1R)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl)methyl]-2-[4-[[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinolin-1-yl]methyl]phenoxy]phenol;Dauricine;dauricine (8ci) |
| CAS: | 524-17-4 |
| MF: | C38H44N2O6 |
| MW: | 624.77 |
| EINECS: | |
| Product Categories: | chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Alkaloids |
| Mol File: | 524-17-4.mol |
DAURICINE Chemical Properties
| Melting point | 115° |
| alpha | D11 -139° in methanol |
| Boiling point | 712.3±60.0 °C(Predicted) |
| density | 1.185±0.06 g/cm3(Predicted) |
| storage temp. | -20°C Freezer, Under inert atmosphere |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | 9.31±0.45(Predicted) |
| color | Pale Beige |
| Water Solubility | 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 DataBase Reference | 524-17-4 |
Safety Information
| Description | As a plant metabolite, Dauricine is a bioactive component derived from Asiatic Moonseed Rhizome and Canadian moonseed, which has been widely used in the treatment of a variety of inflammatory diseases especially in traditional Chinese medicine. It was first synthesized by the scientists from Japan in 1964. It has been proved that Dauricine plays a number of biological roles in the human body, from inhibiting cancer cell growth to blocking cardiac transmembrane Na+, K+, and Ca2+ ion currents. Recent studies suggested that there is novel role of dauricine in preventing or treating cancer. It has been shown to have anti-tumor effects in several cancers, including colon cancer, breast cancer, urinary cancers such as bladder cancer and prostate cancer. |
| References | https://en.wikipedia.org/wiki/Dauricine https://www.ncbi.nlm.nih.gov/pubmed/20509140 |
| Description | Dauricine is a kind of phenolic aromatic compound which is isolated fromMenispermaceae plants such as Asian Menispermum dauricum or CanadianMenispermum dauricum and can be classified as isoquinoline alkaloids. Rhizoma Menispermi is the dry rhizome of Menispermaceae plant Menispermumdauricum. Menispermum dauricum mainly distributes in the northern part of EastAsia and is mainly distributed in the north, east and northeast regions of China. Theusage of Rhizoma Menispermi as a kind of traditional Chinese medicine was firstlyrecorded in Kaibao Herbs with its function of detoxifying many drugs, relievingpains, reducing swelling and sore, curing fever and cough, and killing parasites.According to the Chinese Pharmacopoeia, Rhizoma Menispermi in the north ofChina is different from the herbs used in the south of China known as the samename. Based on the traditional Chinese Medicine theory, Rhizoma Menispermi hasthe 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 liesin the therapy of swollen sore throat, enteritis diarrhea and rheumatic arthralgia.Alkaloid is the main chemical component of Rhizoma Menispermi, and besidesdauricine, there are also other kinds of alkaloids such as dauriciline,O-methyldauricine, and daurisoline in it. |
| Chemical Properties | Derived from the rhizome of the plant Sophora flavescens (Sophora flavescens) of the Menispermaceae family |
| Physical properties | 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 atmosphericpressure. Specific optical rotation: MeOH-139. |
| History | Menispermum dauricum has been long used as a traditional Chinese medicine, butthe research of its effective components has been slow. Dauricine was firstly separatedand structure-confirmed by Fukuda Mayo using alumina column chromatographyseparation assay in 1964. At the same year, dauricine was first synthesizedby two Japanese scientists, Tetsuji Tamayama and Rtani Rikazu, by means of Arndt-Eistertreaction and Bischler-Napieralski reaction. Thereafter, lots of scientistsfrom various countries successively separated daurinoline, Menispermum Xinlinalkali, Menispermum succinylcholine alkali, chelilanthifoline, stepholidine, andmany 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 largenumber of effective components in traditional Chinese herbs were extracted, separatedand applied to clinic. Dauricine was firstly reported on the mainland as anactive ingredient in herbs which can clear away heat and toxic materials. Moreover,dauricine was also used as an antineoplastic and muscle relaxant. There were manymedicines whose principal component was dauricine had been under clinicalresearch for its role of cardiovascular protection since the 1980s, most of thesemedicines were stagnating in phase II clinical trials. |
| Uses | 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. |
| Definition | 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 insinus rhythm, therefore reducing the incidence of arrhythmia. Anti-myocardial ischemia: Dauricine has protective effect on myocardial ischemiaand can improve hemodynamic disturbances during ischemia which is supposedto produce effect via mechanism of improving myocardial metabolism andanti-oxidation. Anti-cerebral ischemia: Dauricine has an effective regulation on gene expression ofBcl-2 and Bax in cortical neurons after the ischemic brain injury, protectingagainst cerebral ischemia. Anti-cerebral ischemia/reperfusion injury: Dauricine can inhibit apoptosis inducedby cerebral ischemia/reperfusion injury by upregulating Bcl-2 expression anddownregulating Bax expression. Also dauricine has the effect of anti-oxidation. Antitumor activity: Dauricine can affect TGF-beta signaling pathway via upregulatinggene expression of DPC4, and then the gene expression of P53 and P16 intumor 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 rapidlyand widely distributed in body and the drug concentration in organs is significantlyhigher than that in plasma, and this is possibly related to its strong lipid solubilityand easy access to cells. |
| Clinical Use | No medicine in the market takes dauricine as the main component up till now. Manyanimal experiments and clinical studies suggest that dauricine can reverse the effectof MDR as verapamil. Since the clinical application of the classical drug verapamilis limited for the serious toxic side effects, the moderate pharmacological effect ofdauricine has a vital clinical significance. The main side effect of dauricine by oralabsorption is gastrointestinal reaction, such as diarrhea, nausea, abdominal distension,and so on. In addition, dauricine can accumulate in the body, leading to hepatorenaltoxicity and central nervous system toxicity. |
DAURICINE Preparation Products And Raw materials
