Berberine
베르베린 · BERBERINE HCL · BBR · berberin · 250Mg · Coptis chinensis extract · BERBERIN HCL · 5,6-DIHYDRO-9,10-DIMETHOXY-BENZO[G]-1,3-BENZODIOXOLO[5,6-A]QUINOLIZINIUM, CHLORIDE
식별자 및 물리적 특성
| CAS No. | 2086-83-1 |
|---|---|
| 분자식 | C20H18NO4+ |
| 평균 분자량 | 336.4 g/mol |
| 단동위원소 질량 | 336.12303448 g/mol |
| SMILES | COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2 |
| InChIKey | YBHILYKTIRIUTE-UHFFFAOYSA-N |
| PubChem CID | 2353 |
| ChEMBL | CHEMBL295124 |
| ChEBI | CHEBI:16118 |
| EC No. | 218-229-1 |
| DTXSID | DTXSID9043857 |
화학 및 물리적 성질
| XLogP | 3.6 |
|---|---|
| 극성 표면적 | 40.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 25 |
| 형식 전하 | 1 |
| 복잡도 | 488 |
| 물질 분류 | Other Uses -> Biochemical Research |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| Dietary Ingredients | Berberine |
| 녹는점 | 145 °C204-206 °C (dec.) |
| Physical Description | Yellow solid[Merck Index] |
| Collision Cross Section | 173.48 Ų [M]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 끓는 점 | 486.8°C (rough estimate) |
| 밀도 | 1.2976 (rough estimate) |
| 굴절률 | 1.5800 (estimate) |
| 저장 조건 | Inert atmosphere,Room Temperature |
| 용해도 | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. |
| 물리적 상태 | 가루 |
| pKa(산도 계수) | 2.47(at 25℃) |
| 색상 | 흰색에서 노란색 결정 |
| 용해도 | 43.48g/L(25℃) |
| InChI | InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1 |
| InChIKey | YBHILYKTIRIUTE-UHFFFAOYSA-N |
| SMILES | O(C1C(=CC=C2C=1C=[N+]1CCC3=CC4OCOC=4C=C3C1=C2)OC)C |
| LogP(분배 계수) | -0.990 (est) |
화학적 성질
White to yellow crystals. Iinsoluble in water; soluble in ether, alcohol. Salts of berberine are berberine bisulfate, berberine sulfate, and berberine hydrochloride. All three are yellow crystals, slightly soluble in water.
안전 및 규제
| 유해성 요약 | Decreased fetal weight (attributed to changes in maternal weight) but no teratogenicity observed in mice and rats[REPROTOX] |
|---|---|
| Hepatotoxicity | Berberine has not been linked to serum enzyme elevations during therapy, although there have been few prospective studies in humans that have reported on its effects on laboratory test results in any detail. In published trials, berberine has appeared to be well tolerated with only minor and few adverse effects which have been similar in frequency among persons receiving placebo. Despite wide scale use as an herbal supplement, berberine has not been linked to published instances of clinically apparent liver injury. The frequency of hypersensitivity reactions to berberine is also not known. |
| 독성 요약 | Sanguinarine [13-methyl (1,3) benzodioxolo(5,6-c)-1,3-dioxolo (4,5) phenanthridinium] kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Berberine, on the other hand, has been reported to cause cytotoxicity and adversely influence the synthesis of DNA. Studies have reported various pharmacological properties of these alkaloids, e.g., they exhibit antibacterial, antiasthma, anticancer, anti-inflammatory, and antidiabetic activities. |
| Effects During Pregnancy and Lactation | ◈ What is berberine? |
| 수질 위해 등급(WGK) | 2 |
| RTECS 번호 | DR9866400 |
| 운송 번호(UN) | 1544 |
| 독성 | LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62 |
| 포장분류 | III |
| 위험 등급 | 6.1(b) |
| F 고인화성물질 | 3-10 |
용도
개요
Coptis chinensis was widely used in China as a folk medicine by Shennong around 3000 BC. Coptis chinensis was first described in the ancient Chinese medical book The Divine Farmer's Herb-Root Classic. Coptis chinensis was used to treat intestinal bacterial infections and antipyretic analgesic for thousands of years agoCoptis chinensis also called zhilian, chuanlian, weilian, jizhualian, shanglian, and xuanlian in Chinese history. Coptis chinensis was accepted by most physicians, and the Chinese pharmacopoeia also uses Coptis chinensis as its official name. Coptis chinensis mainly grows in Anhui, Hunan, Sichuan, and Yunnan and has been cultivated in Sichuan since the Ming dynasty, which has a long history of cultivation. Other species of Coptis chinensis from different places were used as medicine. However, commodity circulation of wild Rhizoma coptidis has not been formed . Coptis chinensis is national three level protection plants at present and majorly produced in Shizhu of Chongqing, West Hubei, Shanxi, and Gansu.Berberine is a quaternary ammonium salt from the protoberberine group of isoquinoline alkaloids. It is found in some plants such as huanglian (Rhizoma coptidis), huangbo (Phellodendri Chinensis) Cortex), sankezhenthree needles (Berberidis Radix), and so on.The components of Coptis chinensis which have antibacterial and antiinflammatory effects are original alkaloid berberine class, including berberine, coptisine, palmatine, epiberberine, columbamine, jatrorrhizine, worenine, and magnoflorine, with berberine having the highest content (5–8%).
역사
Berberine is often used in the form of quaternary ammonium alkali. The solubility of berberine in water is lower, for example, berberine hydrochloride is 1:500, and berberine sulfate is 1:30. In 1926, berberine was first separated from bark of Zanthoxylum clava. Modern pharmacology study showed that berberine has defined structure and is a monomer of traditional Chinese medicine. Berberine can be obtained from many sources and is used in clinics, with reliable pharmacological effects and various and unique mechanisms. At present, berberine can be synthesized by industrial biosynthesis. A series of derivatives can also be synthesized by structure modification, and the pharmacological activities of these derivatives have been tested.
용도
Antiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil