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Berberine information


Berberine
Names
IUPAC name
9,10-Dimethoxy-7,8,13,13a-tetradehydro-2′H-[1,3]dioxolo[4′,5′:2,3]berbin-7-ium
Systematic IUPAC name
9,10-Dimethoxy-5,6-dihydro-2H-7λ5-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ylium[2]
Other names
Umbellatine;[1]
5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;[1]
7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium[1]
Identifiers
CAS Number
  • 2086-83-1 ☒N
3D model (JSmol)
  • Interactive image
Beilstein Reference
3570374
ChEBI
  • CHEBI:16118 checkY
ChEMBL
  • ChEMBL12089 ☒N
ChemSpider
  • 2263 checkY
DrugBank
  • DB04115 checkY
ECHA InfoCard 100.016.572 Edit this at Wikidata
EC Number
  • 218-229-1
KEGG
  • C00757
PubChem CID
  • 2353
UNII
  • 0I8Y3P32UF checkY
CompTox Dashboard (EPA)
  • DTXSID9043857 Edit this at Wikidata
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 checkY
    Key: YBHILYKTIRIUTE-UHFFFAOYSA-N checkY
  • InChI=1/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
    Key: YBHILYKTIRIUTE-UHFFFAOYAJ
SMILES
  • O1c2c(OC1)cc5c(c2)c4cc3ccc(OC)c(OC)c3c[n+]4CC5
Properties
Chemical formula
C20H18NO4+
Molar mass 336.366 g·mol−1
Appearance Yellow solid
Melting point 145 °C (293 °F; 418 K)[3]
Solubility in water
Slowly soluble[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Berberine is a quaternary ammonium salt from the protoberberine group of benzylisoquinoline alkaloids, occurring naturally as a secondary metabolite in some plants including species of Berberis, from which its name is derived.

Due to their yellow pigmentation, raw Berberis materials were once commonly used to dye wool, leather, and wood.[4] Under ultraviolet light, berberine shows a strong yellow fluorescence,[5] making it useful in histology for staining heparin in mast cells.[6] As a natural dye, berberine has a color index of 75160.

  1. ^ a b c The Merck Index, 14th ed., 1154. Berberine
  2. ^ IUPAC Chemical Nomenclature and Structure Representation Division (2013). "P-73.3.1". In Favre HA, Powell WH (eds.). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. IUPAC–RSC. ISBN 978-0-85404-182-4.
  3. ^ a b The Merck Index, 10th Ed. (1983), p.165, Rahway: Merck & Co.
  4. ^ Gulrajani ML (2001). "Present status of natural dyes". Indian Journal of Fibre & Textile Research. 26: 191–201. Archived from the original on 2021-11-20. Retrieved 2017-12-28 – via NISCAIR Online Periodicals Repository.
  5. ^ Weiß D (2008). "Fluoreszenzfarbstoffe in der Natur" (in German). Archived from the original on 9 March 2007. Retrieved 17 July 2009.
  6. ^ "B3251 Berberine chloride form". Sigma-Aldrich. 2013. Archived from the original on 7 September 2012. Retrieved 2 Aug 2013.

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Goldenseal

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Berberis

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alkaloids, especially berberine. A full list of phytochemicals was compiled and published in 2014. The safety of using berberine for any condition is not...

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Berberis aristata

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with opium and lime-juice. The root bark contains the bitter alkaloid berberine, which has been studied for its potential pharmacological properties....

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Coptis chinensis

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chinensis) The rhizomes of Coptis chinensis contain the isoquinoline alkaloids berberine, palmatine, and coptisine among others. Coptis chinensis is one of the...

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Berberis aquifolium

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Northwest Plateau use Oregon grape for indigestion. The plant contains berberine and reportedly has antimicrobial properties similar to those of goldenseal...

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Yellowroot

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plants native to Eastern North America. These plants contain the compound berberine, which gives the roots a yellow color, and have been employed in herbal...

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Huang Bai

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PMID 2816389. Liu, WZ; Peng, WB; Yang, CH (1991). "Berberine-electrochemical detector for the determination of berberine-type alkaloids in various Chinese patent...

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Fluconazole

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arrhythmia if used concurrently with other drugs that prolong the QT interval. Berberine has been shown to exert synergistic effects with fluconazole even in drug-resistant...

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Xanthorhiza

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Florida and west to Ohio and eastern Texas. It contains the alkaloid berberine, which has a number of traditional and contemporary uses for dyeing and...

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Cahill cycle

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Isoquinoline alkaloids

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contains berberine, which also occurs in other plant families, such as the Berberidaceae. An example of the Berberidaceae with the ingredient berberine is Berberis...

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Phellodendron amurense

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isoquinoline alkaloids, palmatine, jatrorrhizine, phellodendorine with berberine found within the leaves. The indole alkaloid has also been found in the...

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Berberis trifoliolata

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and a yellow dye for hides. During early pioneering years, the alkaloid berberine in the agarita roots was used to make a yellow dye. Agarita also has uses...

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Alkaloid

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antibacterial (e.g. chelerythrine), and antihyperglycemic activities (e.g. berberine). Many have found use in traditional or modern medicine, or as starting...

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Benzylisoquinoline

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following compounds: papaverine, noscapine, codeine, morphine, apomorphine, berberine, tubocurarine. (S)-Norcoclaurine (higenamine) has been identified as the...

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SkQ

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penetrating properties. The cations with the well-known medical properties — berberine and palmatine were also tested. SkQBerb and SkQPalm – SkQ derivatives...

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Methamphetamine

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Coptisine

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it is used in Chinese herbal medicine along with the related compound berberine for digestive disorders caused by bacterial infections. Chen J, Wang F...

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Phytochemistry

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MDMA

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Inotrope

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Examples of positive inotropic agents include:[citation needed] Digoxin Berberine Calcium Calcium sensitisers Levosimendan Catecholamines Dopamine Dobutamine...

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Mahonia

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ripened fruits are acidic with a very sharp flavor. The plants contain berberine, a compound found in many Berberis and Mahonia species which causes vomiting...

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Coptis japonica

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Asia it is grown for medicinal purposes, with the main alkaloid being berberine. Rhizomes partly prepared for herbal medicines "Coptis japonica (Thunb...

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