DL-Tetrahydroberberine - CAS 522-97-4

DL-Tetrahydroberberine - CAS 522-97-4 Catalog number: BADC-00077

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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.

General Information

Category
ADCs Cytotoxin
Product Name
DL-Tetrahydroberberine
CAS
522-97-4
Catalog Number
BADC-00077
Molecular Formula
C20H21NO4
Molecular Weight
339.38

Chemical Structure

  • DL-Tetrahydroberberine

Ordering Information

Catalog Number Size Price Stock Quantity
BADC-00077 10 mg $248 In stock
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Purity
95 % (TLC).
Appearance
Greenish Yellow Solid
Synonyms
Canadine; Tetrahydroberberine; Xanthopuccine; Canadin
Solubility
Chloroform; not well in ethanol and methanol.
Storage
Store at +4 °C, in dark place.
Application
ADCs Cytotoxin
Quality Standard
Enterprise Standard
Shelf Life
As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Quantity
Milligrams-Grams
Melting Point
>167°C (dec.)
Canonical SMILES
COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
InChI Key
VZTUIEROBZXUFA-UHFFFAOYSA-N
InChI
InChI=1S/C20H21NO4/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/h3-4,8-9,16H,5-7,10-11H2,1-2H3
1.Tetrahydroberberine, a pharmacologically active naturally occurring alkaloid.
Pingali S1, Donahue JP2, Payton-Stewart F1. Acta Crystallogr C Struct Chem. 2015 Apr;71(Pt 4):262-5. doi: 10.1107/S2053229615004076. Epub 2015 Mar 10.
Tetrahydroberberine (systematic name: 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine), C20H21NO4, a widely distributed naturally occurring alkaloid, has been crystallized as a racemic mixture about an inversion center. A bent conformation of the molecule is observed, with an angle of 24.72 (5)° between the arene rings at the two ends of the reduced quinolizinium core. The intermolecular hydrogen bonds that play an apparent role in crystal packing are 1,3-benzodioxole -CH2···OCH3 and -OCH3···OCH3 interactions between neighboring molecules.

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