Canadine

Base Information

• Chemical Name: Canadine
• CAS No.: 522-97-4
• Deprecated CAS: 4979-14-0,26548-75-4,28111-09-3,29074-38-2,26548-75-4,28111-09-3
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• European Community (EC) Number: 208-338-2
• NSC Number: 94918,36351
• UNII: V2SSH085X8
• DSSTox Substance ID: DTXSID5022724
• Nikkaji Number: J252.482A
• Wikipedia: Canadine
• Wikidata: Q27109653
• Pharos Ligand ID: 29KSTHZTLRHM
• Metabolomics Workbench ID: 129996
• ChEMBL ID: CHEMBL275097
• Mol file: 522-97-4.mol

Synonyms:canadine;canadine hydrochloride;canadine, (+-)-isomer;canadine, (R)-isomer;canadine, (S)-isomer;tetrahydroberberine

Chemical Property of Canadine

Chemical Property:

• Melting Point: 166.5 °C
• Boiling Point: 476.1 °C at 760 mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 141.1 °C
• PSA: 40.16000
• Density: 1.33 g/cm³
• LogP: 3.02590
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >10 mg/mL, soluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 339.14705815
• Heavy Atom Count: 25
• Complexity: 488

Purity/Quality:

98%,99%, ^*data from raw suppliers

Canadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
• 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. Canadine is a protoberberine alkaloid which potently block functional KATP channels natively expressed on midbrain dopamine neurons. Canadine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling.

Technology Process of Canadine

There total 63 articles about Canadine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

(-)-canadine HCl (74203-90-0) → canadine (522-97-4,2086-96-6,5096-57-1,29074-38-2)

Guidance literature:

With sodium hydroxide;

DOI:10.1016/S0040-4020(01)85104-8

Reference yield: 95.0%

7,8-dihydroberberine (483-15-8) → canadine (522-97-4,2086-96-6,5096-57-1,29074-38-2)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; 1,1'-bis{(S)-4,5-dihydro-3H-binaphtho[1,2-C:2',1'-e]phosphino}ferrocene; acetic acid; potassium bromide; In dichloromethane; at 20 ℃; for 100h; under 45603.1 Torr; Catalytic behavior; Autoclave;

Reference yield: 53.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (1356336-77-0) → canadine (522-97-4,2086-96-6,5096-57-1,29074-38-2)

Guidance literature:

formaldehyd; (1S)-1-[3,4-dimethoxy-2-(S)-p-tolylsulfinyl]benzyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline; With trifluoroacetic acid; In toluene; at 140 ℃; for 0.5h; Microwave irradiation;

With sodium hydroxide; In water; pH=8;

DOI:10.1016/j.tet.2011.11.046

upstream raw materials:

(-)-canadine HCl

berberine chloride

(8S,14S)-(-)-8-cyanocanadine

canadine

Downstream raw materials:

12,13-dihydrochelerythrine

berberine iodide

allocryptopine

cis-N-Methylcanadine

Refernces

Structure-activity relationship of isoform selective inhibitors of Rac1/1b GTPase nucleotide binding

10.1016/j.bmcl.2009.08.037

The research aimed at synthesizing and evaluating a series of berberine, phenantridine, and isoquinoline derivatives for their inhibitory activity against Rho GTPase nucleotide binding, with a focus on the isoform selective inhibitors of Rac1/1b GTPase. The study concluded that the insertion of 19 amino acids in the Rac1b splice variant introduces a conformational difference that allows certain compounds, such as 4, 21, 22, and 26, to selectively inhibit Rac1b over Rac1. The chemicals used in the process included protoberberine series compounds like berberine, (±)-canadine, tetrahydroxy berberine analogs, and demethylene berberine, as well as phenantridine alkaloids like chelerythrine and sanguinarine, and 3-aryl-isoquinolines. These compounds were tested for their ability to inhibit Rac1, Rac1b, and Cdc42, with some showing selective inhibition and potential as isoform-selective Rac1b nucleotide binding inhibitors.