Berberine

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
	Other names Umbellatine;; 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;; 7,8,13,13a-Tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium
Identifiers
CAS Number	2086-83-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3570374
ChEBI	CHEBI:16118 ;
ChEMBL	ChEMBL12089 ;
ChemSpider	2263 ;
DrugBank	DB04115 ;
ECHA InfoCard	100.016.572
EC Number	218-229-1;
KEGG	C00757;
PubChem CID	2353;
UNII	0I8Y3P32UF ;
CompTox Dashboard (EPA)	DTXSID9043857 ;
	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 Key: YBHILYKTIRIUTE-UHFFFAOYSA-N ; 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)
Solubility in water	Slowly soluble
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Berberine is an organic compound classified as benzylisoquinoline alkaloid. Chemically, it is a quaternary ammonia compound.

Its name is derived from the genus of plants, Berberis. Berberine occurs in the roots, bark, stems, and leaves of Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal).

Due to their yellow pigmentation, raw Berberis materials were once commonly used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence. As a natural dye, berberine has a color index of 75160.

Plants containing berberine have been used in traditional medicine, and berberine extracts are sold as dietary supplements. Other than in China as an over-the-counter drug, berberine is not approved as a prescription drug, regulated or proven safe in any country.