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Canadine information


Canadine
Names
IUPAC name
9,10-Dimethoxy-2′H-[1,3]dioxolo[4′,5′:2,3]berbine
Systematic IUPAC name
(13aS)-9,10-Dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline
Other names
(S)-Tetrahydroberberine; Xanthopuccine
Identifiers
CAS Number
  • 522-97-4 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL490533 checkY
ChemSpider
  • 19910
ECHA InfoCard 100.023.468 Edit this at Wikidata
KEGG
  • C03329 checkY
  • C11818
PubChem CID
  • 21171
UNII
  • V2SSH085X8 checkY
CompTox Dashboard (EPA)
  • DTXSID10110003 Edit this at Wikidata
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/t16-/m0/s1
    Key: VZTUIEROBZXUFA-INIZCTEOSA-N
SMILES
  • O1c2c(OC1)cc3c(c2)CCN5[C@H]3Cc4ccc(OC)c(OC)c4C5
Properties
Chemical formula
C20H21NO4
Molar mass 339.391 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup, and is present in many plants from the family Papaveraceae, such as Corydalis yanhusuo and C. turtschaninovii.

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Canadine

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(S)-Canadine, also known as (S)-tetrahydroberberine and xanthopuccine, is a benzylisoquinoline alkaloid (BIA), of the protoberberine structural subgroup...

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individually as the Southport Sockmen. Steven Bain, Steven Gawthrop and Paul Canadine would approach people in bars and clubs in Southport and buy the socks...

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Corydalis

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Many of the species in Corydalis contain other toxins and alkaloids like canadine, which blocks calcium. The species C. caseana is poisonous to livestock...

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Corydalis Alkaloids

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(also known as d- or (+)-stylopine), d-canadine, and hydrohydrastinine. d- or (+)-Stylopine. d- or (+)-Canadine Hydrohydrastinine Corydalis alkaloids exhibit...

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Goldenseal

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hydrastine, berberine, berberastine, hydrastinine, tetrahydroberberastine, canadine and canalidine. A related compound, 8-oxotetrahydrothalifendine, was identified...

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Noscapine

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the 9-hydroxyl group. Canadine synthase (CAS) catalyzes the formation of a unique C2-C3 methylenedioxy bridge in (S)-canadine. An N-methylation (TNMT)...

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Ketamine

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Methylenedioxy

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phenol and methoxy group. Examples of products formed by this process are canadine and berberine. Similarly, ortho-demethylenation can be carried out by other...

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Berberine reductase

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reaction (R)-canadine + 2 NADP+ ⇌ {\displaystyle \rightleftharpoons } berberine + 2 NADPH + H+ Thus, the two substrates of this enzyme are (R)-canadine and nicotinamide...

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Pregabalin

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Promethazine

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Alkaloid

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