canadine

Names

[ Name ]:
canadine

[Synonym ]:
(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
Hydroberberine
6H-1,3-Benzodioxolo[5,6-a]benzo[g]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-
9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
canadine
(±)-Canadine
5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine
HDHHC
dl-Tetrahydroberberine
a-Canadine
6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-
HU243
9,10-bis(methyloxy)-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline
xanthopuccine
(S)-Canadine
6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
(13aS)-9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine
(S)-Tetrahydroberberine
6H-1,3-Benzodioxolo[5,6-a]benzo[g]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-
dl-Canadine
UNII:V2SSH085X8
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
(-)-Canadine
Tetrahydroberberine
CANADINE, (-)-
(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

Biological Activity

[Description]:

(S)-(-)-Tetrahydroberberine is an alkaloid and intermediate in the biosynthesis of berberine with insecticidal activity[1].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[References]

[1]. Galanie S, Smolke CD. Optimization of yeast-based production of medicinal protoberberine alkaloids. Microb Cell Fact. 2015 Sep 16;14:144.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
476.1±45.0 °C at 760 mmHg

[ Melting Point ]:
135°

[ Molecular Formula ]:
C₂₀H₂₁NO₄

[ Molecular Weight ]:
339.385

[ Flash Point ]:
141.1±25.9 °C

[ Exact Mass ]:
339.147064

[ PSA ]:
40.16000

[ LogP ]:
3.83

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.656

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DR9823000

CHEMICAL NAME :: 13a-alpha-Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-

CAS REGISTRY NUMBER :: 5096-57-1

LAST UPDATED :: 199503

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C20-H21-N-O4

MOLECULAR WEIGHT :: 339.42

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 940 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,262,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 790 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,262,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,262,1989

Safety Information

[ Hazard Codes ]:
Xi

[ RIDADR ]:
1544

[ Packaging Group ]:
III

Related Compounds

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