CAS 5096-57-1

Canadine

Description:

Canadine, with the CAS number 5096-57-1, is a naturally occurring alkaloid primarily found in various plant species, particularly within the Papaveraceae family. It is characterized by its structural framework, which includes a benzylisoquinoline core. This compound exhibits a range of biological activities, including analgesic and anti-inflammatory properties, making it of interest in pharmacological research. Canadine is typically a yellowish crystalline solid and is soluble in organic solvents, but its solubility in water is limited. The compound's pharmacokinetics and mechanisms of action are still under investigation, but it is believed to interact with various neurotransmitter systems. Additionally, it may have potential applications in traditional medicine, although further studies are needed to fully understand its therapeutic potential and safety profile. As with many alkaloids, caution is advised regarding its use, as it may exhibit toxicity at higher concentrations.

Formula: C₂₀H₂₁NO₄

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-INIZCTEOSA-N

SMILES: O(C)C1=C2CN3[C@](C=4C(=CC5=C(C4)OCO5)CC3)(CC2=CC=C1OC)[H]

Synonyms:

• (-)-Canadine
• (-)-Tetrahydroberberine
• (-)-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)-(-)-7,8,13,13a-Tetrahydroberberine
• (S)-(-)-Canadine
• (S)-(-)-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

6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine,5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-

CAS: 5096-57-1

Formula: C₂₀H₂₁NO₄

Color and Shape: Solid

Molecular weight: 339.3850

Ref: IN-DA00DEW9

(S)-(-)-Canadine

CAS: 5096-57-1

(S)-(-)-Canadine (tetrahydroberberine) is a naturally occurring isoquinoline alkaloid, acting as a D2 receptor antagonist and 5-HT1A receptor agonist.

Formula: C₂₀H₂₁NO₄

Purity: 98%

Color and Shape: Solid

Molecular weight: 339.39

Ref: TM-TN3574

Canadine

CAS: 5096-57-1

Formula: C₂₀H₂₁NO₄

Purity: 95%~99%

Color and Shape: Powder

Molecular weight: 339.391

Ref: BP-SBP01813

(S)-(-)-Canadine

CAS: 5096-57-1

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)

Formula: C₂₀H₂₁NO₄

Color and Shape: Neat

Molecular weight: 339.38

Ref: TR-C175180

(S)-(-)-Canadine

CAS: 5096-57-1

Canadine is an alkaloid and the major active ingredient in the herbal medicine berberine. It has been used for the treatment of metabolic disorders, such as diabetes mellitus. Canadine can cause drug interactions with other drugs that are metabolized by cytochrome P450 enzymes and may increase oxidative injury to cells. Canadine has also shown efficacy against oral pathogens in animal models. Toxicological studies have been conducted on rats, showing that it may cause liver damage and energy metabolism disturbances. This drug has been found to be effective for treating some experimental models of liver disease such as chronic hepatitis or cirrhosis.

Formula: C₂₀H₂₁NO₄

Purity: Min. 95%

Molecular weight: 339.4 g/mol

Ref: 3D-FAA09657