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Substance Name: Berberine
RN: 2086-83-1
UNII: 0I8Y3P32UF
InChIKey: YBHILYKTIRIUTE-UHFFFAOYSA-N

Note

  • An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.

Molecular Formula

  • C20-H18-N-O4

Molecular Weight

  • 336.3652
 

Classification Code

  • Mutation Data
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Names and Synonyms

Name of Substance

  • Berberine

MeSH Heading

  • Berberine

Synonyms

  • 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium
  • Berberin
  • Berberine
  • BRN 3570374
  • EINECS 218-229-1
  • UNII-0I8Y3P32UF

Systematic Names

  • Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-
  • Berberine
  • Berbinium, 7,8,13,13a-tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-

Registry Numbers

CAS Registry Number

  • 2086-83-1

FDA UNII

  • 0I8Y3P32UF

System Generated Number

  • 0002086831

Structure Descriptors

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

c12c3c(cc4OCOc4c3)CC[n+]1cc1c(c(OC)ccc1c2)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 329mg/kg (329mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 82, Pg. 726, 1962.
mouse LD50 subcutaneous 18mg/kg (18mg/kg)   Russian Pharmacology and Toxicology Vol. 31, Pg. 129, 1968.
rabbit LDLo subcutaneous 100mg/kg (100mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LD intraperitoneal > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 17, 1953.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 145 deg C   EXP
log P (octanol-water) 2.080 (none)   EST
Atmospheric OH Rate Constant 2.09E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.