(S)-(-)-Canadine

CAS: 5096-57-1

Ref. TR-C175180

Product Information

• Name: (S)-(-)-Canadine
• Synonyms: (S)-5,8,13,13a-tetrahydro-9,10-dimethoxy-6H-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, Canadine, (-)-Canadine, (-)-Tetrahydroberberine, (-)-a-Canadine, (S)-(-)-7,8,13,13a-Tetrahydroberberine, (S)-(-)-Tetrahydroberberine, (S)-Tetrahydroberberine, 9,10-Dimethoxy-2,3-(methylenedioxy)-13aa-berbine, l-Canadine, a-Canadine, (-)-α-Canadine, (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, (D,L)-Tetrahydroberberine, (S)-9,10-Dimethoxy-6,8,13,13a-tetrahydro-5H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline, 13aα-Berbine, 9,10-dimethoxy-2,3-(methylenedioxy)-, 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)-, 9,10-Dimethoxy-2,3-(methylenedioxy)-13aα-berbine, 9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline, O-Methyl Nandinine

Description

Applications (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.
References Sun, H. et al.: Bioorg. Med. Chem., 21, 856 (2013); Deeb, O., et al.: Chem. Biol. Drug Des., 76, 255 (2010); Sun., et al.: Br. J. Pharmcol., 158, 1302 (2009); Duchowicz, P., et al.: Bioorg. Med. Chem., 14, 5876 (2006); Yamahara, J. et al.: Chem. Pharm. Bull., 24, 1909 (1976)

• Brand: TRC

Chemical properties

• Molecular weight: 339.38
• Formula: C₂₀H₂₁NO₄
• Color/Form: Neat
• 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
• InChI key: InChIKey=VZTUIEROBZXUFA-UHFFFAOYSA-N
• SMILES: COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1C2)OCO4