COPTISINE CHLORIDE(P)
Coptisine chloride
CAS: 6020-18-4
Molecular Formula: C19H14ClNO4
COPTISINE CHLORIDE(P) - Names and Identifiers
| Name | Coptisine chloride |
| Synonyms | Coptisine Hcl Coptisine chloride COPTISINE CHLORIDE COPTISINE CHLORIDE(P) Coptisine Hydrochloride COPTISINECHLORIDE(P)(PLEASECALL) 2,3,9,10-BISMETHYLENEDIOXYPROTOBERBERINE 6,7-dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinolin-5-ium 7,12b-dihydro-6H-[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoline 6,7-dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinolin-5-ium chloride |
| CAS | 6020-18-4 |
| EINECS | 611-948-5 |
| InChI | InChI=1/C19H15NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,5-8,15H,3-4,9-10H2 |
COPTISINE CHLORIDE(P) - Physico-chemical Properties
| Molecular Formula | C19H14ClNO4 |
| Molar Mass | 355.77 |
| Density | 1.51g/cm3 |
| Melting Point | >258°C (dec.) |
| Boling Point | 601.5°C at 760 mmHg |
| Flash Point | 190.4°C |
| Solubility | Very slightly soluble in water, slightly soluble in ethanol, soluble in alkali |
| Vapor Presure | 2E-14mmHg at 25°C |
| Appearance | Orange prism crystal |
| Color | Orange to Dark Orange |
| Storage Condition | Inert atmosphere,2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.749 |
| MDL | MFCD00016676 |
| Physical and Chemical Properties | Very slightly soluble in water, slightly soluble in ethanol, soluble in alkali from the Papaveraceae plant |
COPTISINE CHLORIDE(P) - Reference
| Reference Show more | 1. Chen Yang, Cui Bo, fan Yanhao, etc. Study on the difference of intestinal absorption of gegen Qinlian decoction in normal and large intestine damp-heat model rats [J]. Chinese Journal of Traditional Chinese Medicine, 2020, v.45(01):177-186. 2. Chen Kai, Li Hui, Wang Jia Qi, Wang Moon, Song Ming-Ming, Ding Chuan Bo, Liu Yitong, Liu Wen Cong, Zheng Yi male. Study on the variation of compatibility ratio and pH value environment on the dissolution of four kinds of alkaloids after Coptis-rhubarb compatibility based on one test and multiple evaluation method [J]. Chinese Herbal Medicine, 2016,47(10):1709-1713. 3. Zhang Chungang, Tang Jingya, Yu Changchen, etc. Extraction, purification and content determination of five main alkaloids from Coptis chinensis [J]. Modern Chinese medicine, 2018, 20(09):116-119 126. 4. Li shujiao, Wang Yuqing. On-line screening of antioxidant substances from Coptis chinensis by HPLC-ABTS-DAD-Q-TOF/MS [J]. Chinese Journal of Traditional Chinese Medicine 2018(12). 5. Liu Yang, Yin Xiuwen, Wang Ziyu, etc. Study on biopharmaceutics classification system of Coptis chinensis extracts [J]. Chinese Journal of Traditional Chinese Medicine, 2017, 21(v.42):87-94. 6. Zhang Jiuxu, Fan Jing, Li Xiaoyang, et al. Study on processing method of modern producing area of Coptis chinensis based on internal quality [J]. Journal of Liaoning University of Traditional Chinese Medicine, 2019, v.21;No.185(09):74-77. 7. Wu Yichen, Xie Hui, Mao Chunqin, et al. HPLC fingerprint of compound gancao Qingyang mixture [J]. Chinese patent medicine, 2019, 041(009):2251-2256. 8. Sheng-Yun, D. A. I ., et al. "Establishment and reliability evaluation of the design space for HPLC analysis of six alkaloids in Coptis chinensis (Huanglian) using Bayesian approach." Chinese journal of natural medicines 14.9 (2016): 697-708.https://doi.org 9. Zhang, Y., Wang, Z., Xu J. et al. Optimization of the extraction and purification of Corydalis yanhusuo W.T. Wang based on the Q-marker uniform design method. BMC Chemistry 14, 9 (2020). https://doi.org/10.1186/s13065-020-00666-6 10. [IF=3] Sheng-Yun DAI et al."Establishment and reliability evaluation of the design space for HPLC analysis of six alkaloids in Coptis chinensis (Huanglian) using Bayesian approach."Chin J Nat Medicines. 2016 Sep;14:697 11. [IF=4.759] Yi Zhang et al."Screening of inhibitors against histone demethylation jumonji domain-containing protein 3 by capillary electrophoresis."J Chromatogr A. 2020 Feb;1613:460625 |
COPTISINE CHLORIDE(P) - Reference Information
| plant sources and pharmacological effects | coptisine hydrochloride is also known as chlorinated coptisine and coptisine, it is an alkaloid extracted from the rhizome of Coptis chinensis of Ranunculaceae family. It has anti-microbial activity, and its anti-Karl yeast effect is stronger than berberine, palmatine and African Tetrandrine; Insecticidal activity; induces differentiation of nerve cells; Has a protective effect on the gastric mucosa; Anti-cancer effect; The role of the immune system; Smooth muscle relaxation effect; Anti-nephritis effect. |
| synthetic method | coptisine is a quaternary ammonium alkaloid extracted from Coptis chinensis and other plants, which has a variety of pharmacological effects, such as anti-tumor, hypoglycemic, immune regulation and improve cardiovascular function. The low content of coptisine in plants limits its further research and application. This method is based on 2, 3-dimethoxybenzaldehyde as starting material, by demethyl, ring and condensation and ring-closing reaction of 5 step synthesis of hydrochloric acid coptisine. FIG. 1 is a chemical reaction scheme for the artificial synthesis of coptisine hydrochloride. |
| biological activity | Coptisine (Q-100696, NSC-119754) is an indole bipyridine alkaloid isolated from Coptis chinensis Franch, with anti-diabetic, antibacterial, antiviral, anti-liver cancer and anti-leukemia effect. Coptisine chloride is also a potent inhibitor of non-competitive IDO, corresponding to IC50 and Ki values of 6.3 μm and 5.8 μm, respectively. |
| Target | Value |
| IDO (Cell-free assay) | 5.8 μM(Ki) 6.3 μM |
| Use | for content determination/identification/pharmacological experiments. Pharmacological Efficacy: anti-microbial activity, the effect of anti-Karl yeast than berberine, palmatine and African Tetrandrine are strong; Insecticidal activity; Induced differentiation of nerve cells; The gastric mucosa has a protective effect; anticancer effect; The role of the immune system; Smooth muscle relaxation; Anti-nephritis effect. |
Last Update：2024-04-09 15:16:51
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