ChemicalBook--->CAS DataBase List--->522-97-4

522-97-4

522-97-4 Structure

522-97-4 Structure
IdentificationBack Directory
[Name]

Tetrahydroberberine
[CAS]

522-97-4
[Synonyms]

THB
CANADINE
Nsc94918
l-Canadine
DL-CANADINE
AKOS 213-56
Xanthopuccine
l-Xanthopuccine
TETRAHYDROBERBERINE
l-Tetrahydroberberine
Berberine, tetrahydro-
DL-TETRAHYDROBERBERINE
Tetrahydroberberine, BR
Tetrahydroberberine,THB
Tetrahydroberberine, Canadine
Tetrahydroberberine USP/EP/BP
9-Deoxy-16,17-dihydroberberine
dl-Tetrahydroberberine 〔dl-Canadine〕
9,10-DiMethoxy-2,3-(Methylenedioxy)berbine
Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-
Tetrahydroberberine, 98%, from Coptis chinensis Franch.
5,8,13,13a-tetrahydro-9,10-dimethoxy-6H-benzo[g]benzo-1,3-dioxolo[5,6-a]quinolizine
5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
6H-Benzo[G]-1,3-benzodioxolo[5,6-A]quinolizine, 5,8,13,13A-tetrahydro-9,10-dimethoxy-
9,10-DIMETHOXY-5,8,13,13A-TETRAHYDRO-6H-[1,3]DIOXOLO[4,5-G]ISOQUINO[3,2-A]ISOQUINOLINE
5,8,13,13A-TETRAHYDRO-9,10-DIMETHOXY-6H-BENZO[G]-1,3-BENZODIOXOLO[5,6-ALPHA]QUINOLIZINE
(13aR)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine
Canadine, THB, 5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-alpha]quinolizine
[EINECS(EC#)]

208-338-2
[Molecular Formula]

C20H21NO4
[MDL Number]

MFCD00067284
[MOL File]

522-97-4.mol
[Molecular Weight]

339.39
Chemical PropertiesBack Directory
[Melting point ]

166.5 °C
[Boiling point ]

476.1±45.0 °C(Predicted)
[density ]

1.33±0.1 g/cm3(Predicted)
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO: >10 mg/mL, soluble
[form ]

solid
[pka]

6.53±0.20(Predicted)
[color ]

yellow
[biological source]

(Corydalis yanhusuo)
[InChIKey]

VZTUIEROBZXUFA-UHFFFAOYSA-N
[SMILES]

N21C(Cc5c(c(c(cc5)OC)OC)C2)c3c(cc4c(c3)OCO4)CC1
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[Safety Statements ]

36
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
[Toxicity]

LD50 in mice (mg/kg): 940 orally; 790 s.c.; 100 i.v. (Sadritdinov, Sultanov)
Hazard InformationBack Directory
[Chemical Properties]

Pale yellow crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Phellodendron chinense, Corydalis yanhusuo root tuber, and Rhizoma Corydalis.
[Uses]

Tetrahydroberberine is a protoberberine alkaloid which potently block functional KATP channels natively expressed on midbrain dopamine neurons. Tetrahydroberberine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling.
[Definition]

ChEBI: A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10.
[Biological Activity]

Dopamine receptor antagonist; nicotinic acetylcholine receptor (α4β2α4β4α7α1β1γδ) modulator; induces clearance of low-density lipoprotein in mice.

Tetrahydroberberine (Canadine)an isoquinoline alkaloid isolated from corydalis tuberis a potent dopamine D2 receptor antagonist (pKi = 6.08) and nicotinic acetylcholine receptor (α4β2α4β4α7 α1β1γδ) modulator. Tetrahydroberberine alleviates high-f at diet-induced hyperlipidemia and induces clearance of low-density lipoprotein and intermediate-density lipoprotein in mice.
[in vivo]

Tetrahydroberberine (30 μg/kg; IV) causes a dramatic increase in gastric regulatory capacity in beagle dogs, significantly enhances gastric contractility and shortens contraction intervals in rats, and enhances gastric motility function in the upper gastrointestinal tract[1].

Spectrum DetailBack Directory
[Spectrum Detail]

Tetrahydroberberine(522-97-4)1HNMR
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