Dauricine

Base Information

• Chemical Name: Dauricine
• CAS No.: 524-17-4
• Molecular Formula: C38H44N2O6
• Molecular Weight: 624.777
• European Community (EC) Number: 683-103-9
• UNII: 8QTO90G5W5
• DSSTox Substance ID: DTXSID90966808
• Nikkaji Number: J8.642H
• Wikipedia: Dauricine
• Wikidata: Q5228100
• Metabolomics Workbench ID: 53122
• ChEMBL ID: CHEMBL442717
• Mol file: 524-17-4.mol

Synonyms:4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)phenol;dauricine;dauricine monohydrochloride

Chemical Property of Dauricine

Chemical Property:

• Appearance/Colour: White powder.
• Vapor Pressure: 5.76E-21mmHg at 25°C
• Melting Point: 115oC
• Refractive Index: 1.601
• Boiling Point: 712.3 °C at 760 mmHg
• PKA: 9.31±0.45(Predicted)
• Flash Point: 384.6 °C
• PSA: 72.86000
• Density: 1.185 g/cm³
• LogP: 6.63810
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 624.31993713
• Heavy Atom Count: 46
• Complexity: 933

Purity/Quality:

99% ^*data from raw suppliers

Dauricine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)OC4=C(C=CC(=C4)CC5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)OC4=C(C=CC(=C4)C[C@@H]5C6=CC(=C(C=C6CCN5C)OC)OC)O)OC)OC
• 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. 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.
• 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 atmospheric pressure. Specific optical rotation: MeOH-139.
• 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.
• 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.