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Details

Stereochemistry ACHIRAL
Molecular Formula C19H14NO4.Cl
Molecular Weight 355.772
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Coptisine chloride

SMILES

[Cl-].C1OC2=C(O1)C=C3C(CC[N+]4=C3C=C5C=CC6=C(OCO6)C5=C4)=C2

InChI

InChIKey=LUXPUVKJHVUJAV-UHFFFAOYSA-M
InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H14NO4
Molecular Weight 320.3188
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Coptisine (COP), a protoberberine alkaloid, is widely found in Chinese medicinal plants (family Berberidaceae, Ranunculaceae and Papaveraceae). It is reported that COP has a wide range of pharmacological and biological activities, including antibacterial, hypoglycemic, anti-tumorigenic, and gastric-mucous membrane protection. Considerable attention has been focused on its activity against central nervous system disorders, such as improving the symptoms of Alzheimer’s disease and even preventing its onset, by exerting antidepressant effects as a potent type A monoamine oxidase inhibitor. Coptisine was found to be an efficient uncompetitive Indoleamine 2,3-dioxygenase inhibitor. Coptisine is a potent inhibitor of human organic cation transporters.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.9 µM [IC50]
2.3 µM [IC50]
2.3 µM [IC50]
6.3 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice: 50,100 or 150mg/kg body weight daily
Route of Administration: Oral
In Vitro Use Guide
In HCT-116 cells, Coptisine exhibited cell cytotoxicity at a high rate (IC50 was 27.13 μg/mL vs 282.2 μg/mL in human colorectal epithelial cells FHC). Besides, Coptisine (2.5 μg/mL) decreased the survival rate of cells time-dependently .
Substance Class Chemical
Record UNII
4RSB8UY88E
Record Status Validated (UNII)
Record Version