8-Oxyberberine

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Names

[ CAS No. ]:
549-21-3

[ Name ]:
8-Oxyberberine

[Synonym ]:
8H-1,3-Benzodioxolo[5,6-a]benzo[g]quinolizin-8-one, 5,6-dihydro-9,10-dimethoxy-
8-oxoberberine
9,10-Dimethoxy-5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-8-one
9,10-Dimethoxy-5,6-dihydro-8H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-one
Ketoberberine
berberin-8-one
Berlambine

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
611.5±55.0 °C at 760 mmHg

[ Melting Point ]:
200-201ºC

[ Molecular Formula ]:
C20H17NO5

[ Molecular Weight ]:
351.353

[ Flash Point ]:
323.6±31.5 °C

[ Exact Mass ]:
351.110687

[ PSA ]:
58.92000

[ LogP ]:
3.87

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.691

[ Water Solubility ]:
Insuluble (1.8E-3 g/L) (25 ºC)

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DS0180000
CHEMICAL NAME :
8-Berbinone, 13,13a-didehydro-9,10-dimethoxy-2,3-(methylenedioxy)-
CAS REGISTRY NUMBER :
549-21-3
BEILSTEIN REFERENCE NO. :
0339209
LAST UPDATED :
199709
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C20-H17-N-O5
MOLECULAR WEIGHT :
351.38
WISWESSER LINE NOTATION :
T G5 D6 C666 HO JO ONV IH&&T&&J RO1 SO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory stimulation
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 15,486,1981

Safety Information

[ Hazard Codes ]:
Xi

Synthetic Route

Precursor & DownStream

Precursor

  • Berberine hydrochloride
  • Berberine
  • 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-9,10-dimethoxy-
  • 1,3-Dioxolo[4,5-g]isoquinoline, 7,8-dihydro-5-methyl-
  • Berberinol
  • Chloroform
  • 7,8-Dihydro-1,3-dioxolo[4,5-g]isoquinoline
  • Anhydride of 3,4-dimethoxyhomophthalic acid

DownStream

  • 8H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin-8-one,5,6-dihydro-9-hydroxy-10-methoxy-
  • (9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-phenyl-amine
  • 8-carboxymethyl-9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolinylium, chloride
  • 8-Canadinylacetic acid
  • 8,8-diethyldihydroberberine
  • 2-(9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-3-oxo-butyric acid ethyl ester
  • (9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-8-ylidene)-malononitrile

Related Compounds

  • 8-Fluoro-imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester
  • 8-methyl-1,2,3,4-tetrahydronaphthalene-1-carbaldehyde
  • 8-Amino-5-aza-spiro[2.5]octane-5-carboxylic acid tert-butyl ester
  • 8-methyl-4-propan-2-ylspiro[4.5]deca-1,8-dien-3-one
  • 8-benzyl-7-phenyl-2,3-dihydro-pyrido[3,4-d]pyridazine-1,4-dione
  • 8-chloro-4-sulfanylidenechromene-3-carbaldehyde
  • 3-fluoro-N-(6-((2-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)ethyl)thio)pyridazin-3-yl)benzamide
  • Methyl 2-((6-(cyclopropanecarboxamido)pyridazin-3-yl)thio)propanoate
  • Ethyl 2-((6-(cyclopropanecarboxamido)pyridazin-3-yl)thio)butanoate
  • I+/--Ethyl-N-(2,4,6-trichlorophenyl)benzenemethanamine
  • N-(6-((2-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)ethyl)thio)pyridazin-3-yl)cyclopropanecarboxamide
  • N-(6-((2-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)ethyl)thio)pyridazin-3-yl)propionamide
  • N-(6-((2-oxo-2-(((tetrahydrofuran-2-yl)methyl)amino)ethyl)thio)pyridazin-3-yl)thiophene-2-carboxamide
  • 4-(N-cyclohexyl-N-methylsulfamoyl)-N-(1,3-dimethyl-1H-pyrazol-5-yl)benzamide
  • 1-((4-chlorophenyl)sulfonyl)-N-(1,3-dimethyl-1H-pyrazol-5-yl)pyrrolidine-2-carboxamide
  • N-(1,3-dimethyl-1H-pyrazol-5-yl)-1-tosylpiperidine-3-carboxamide
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