(S)-Canadine

Base Information

• Chemical Name: (S)-Canadine
• CAS No.: 5096-57-1
• Molecular Formula: C₂₀H₂₁NO₄
• Molecular Weight: 339.391
• European Community (EC) Number: 225-815-0
• UNII: Q97V5BUT9D
• DSSTox Substance ID: DTXSID10110003
• Nikkaji Number: J71.178K
• Wikipedia: Canadine
• Wikidata: Q4382087
• Pharos Ligand ID: 29KBGQNDA7PC
• Metabolomics Workbench ID: 50557
• ChEMBL ID: CHEMBL490533
• Mol file: 5096-57-1.mol

Synonyms:5096-57-1;(S)-Canadine;Canadine l-form;(S)-Tetrahydroberberine;(-)-Canadine;(-)-Tetrahydroberberine;(S)-(-)-Canadine;(S)-(-)-Tetrahydroberberine;Canadine, (-)-;EINECS 225-815-0;UNII-Q97V5BUT9D;Q97V5BUT9D;9,10-Dimethoxy-2,3-(methylenedioxy)berbine;CHEBI:16592;NSC 36351;5,6,13,13a-Tetrahydro-9,10-dimethoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine;6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (S)-;(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene;l-Canadine;13a-alpha-BERBINE, 9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-;(13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine;(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline;alpha-canadine;6H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINE, 5,8,13,13A-TETRAHYDRO-9,10-DIMETHOXY-, (13AS)-;6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-;6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (S)-;canadine, (S)-isomer;.ALPHA.-CANADINE;Canadine (Tetrahydroberberine);CANADINE L-FORM [MI];SCHEMBL432394;CHEMBL490533;DTXSID10110003;HY-N1418;BDBM50429047;CCG-36046;AKOS032962408;LS-43450;CS-0016842;C03329;Q4382087;Z2216911272;13a.alpha.-Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-;9,10-Dimethoxy-5,8,13,13a-tetrahydro-6H-benzo[g][1,3]benzodioxolo[5,6-a]quinolizine;(13aS)-5, 8, 13, 13a-tetrahydro-9, 10-dimethoxy-6H-benzo[g] -1,3-benzodioxolo[5, 6-a]quinolizine;(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline

Chemical Property of (S)-Canadine

Chemical Property:

• Vapor Pressure: 3.13E-09mmHg at 25°C
• Melting Point: 135°
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 476.1°Cat760mmHg
• PKA: 6.53±0.20(Predicted)
• Flash Point: 141.1°C
• PSA: 40.16000
• Density: 1.33g/cm³
• LogP: 3.02590
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated)
• 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%Min ^*data from raw suppliers

(S)-(-)-Canadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C2=C(CC3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
• Isomeric SMILES: COC1=C(C2=C(C[C@H]3C4=CC5=C(C=C4CCN3C2)OCO5)C=C1)OC
• Uses: (S)-(-)-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. (S)-(-)-Canadine has a strong central nervous system-depressing activity and is used in the preparation of tetrahydroprotoberberine derivatives as n ew antipsychotic agents. (S)-(-)-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. (S)-(-)-Canadine has a strong central nervous system-depressing activity and is used in the preparation of tetrahydroprotoberberine derivatives as new antipsychotic agents.

Technology Process of (S)-Canadine

There total 63 articles about (S)-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:

7,8-dihydroberberine

berberine iodide

berberine hydroxide

cis-N-Methylcanadine