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Details

Stereochemistry ACHIRAL
Molecular Formula C20H17NO5
Molecular Weight 351.3527
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 8-OXYBERBERINE

SMILES

COC1=C(OC)C2=C(C=C1)C=C3N(CCC4=C3C=C5OCOC5=C4)C2=O

InChI

InChIKey=ZHYQCBCBTQWPLC-UHFFFAOYSA-N
InChI=1S/C20H17NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9H,5-6,10H2,1-2H3

HIDE SMILES / InChI
8-oxyberberine (8-Oxoberberine, JKL1073A), an oxoderivative of berberine, is an alkaloid isolated from Argemone mexicana. 8-oxyberberine has been initially reported to exert anti-proliferative effects against a series of cancers. 8-oxyberberine inhibited the cell proliferation in human colon cancer cells. 8-Oxoberberine, a derivative of berberine, has been reported to exert antiarrhythmic activity, much like a class III antiarrhythmic agent. 8-Oxoberberine, like berberine, exerted positive inotropic and negative chronotropic actions. In rat left atria 8-oxoberberine, 10 to 100 uM, increased atrial contractility. In spontaneously beating right atria, 8-oxoberberine increased atrial contractility but slightly decreased the rate of contractions. 8-Oxoberberine inhibited the integral of the transient outward current (Ito) with a KD value of approximately 4 uM in either human or rat atrial myocytes. 8-Oxoberberine inhibited Ito by binding to open-state channels or by shifting the steady state inactivation curve of Ito.

CNS Activity

Curator's Comment: TOXIC EFFECTS : Behavioral - convulsions or effect on seizure threshold Behavioral - changes in motor activity (specific assay)

Approval Year

PubMed

PubMed

TitleDatePubMed
Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.
2012 Apr 15
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: mouse:LD50- 240mg/kg, intraperitoneal. https://chem.nlm.nih.gov/chemidplus/rn/549-21-3
Nasal irrigation solution
Route of Administration: Nasal
In Vitro Use Guide
Curator's Comment: 8-Oxyberberine exhibited mild to potent cytotoxicity depending on the time of exposure and concentration used. It reduced cell viability by 27% at a concentration of 200 mg/mL at 24 h. However, cell viability was reduced by more than 76% at a concentration of 125 mg/mL at 48 h post-treatment.
At 200 ug/mL, 8-Oxyberberine was mildly cytotoxic (∼27%) at 24 h but was more potent (∼76%) at 48 h to SW480 human colon cancer cell line.
Name Type Language
8-OXYBERBERINE
Common Name English
8-OXOBERBERINE
Common Name English
KETOBERBERINE
Common Name English
8-BERBINONE, 13,13A-DIDEHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-
Common Name English
BERBERIN-8-ONE
Common Name English
JKL 1073A
Code English
BERLAMBINE
Common Name English
OXYBERBERINE
Common Name English
NSC-93138
Code English
8H-BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZIN-8-ONE, 5,6-DIHYDRO-9,10-DIMETHOXY-
Systematic Name English
JKL-1073A
Code English
9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-13,13A-DIDEHYDRO-8-BERBINONE
Common Name English
Code System Code Type Description
PUBCHEM
11066
Created by admin on Fri Dec 15 20:33:02 GMT 2023 , Edited by admin on Fri Dec 15 20:33:02 GMT 2023
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CAS
549-21-3
Created by admin on Fri Dec 15 20:33:02 GMT 2023 , Edited by admin on Fri Dec 15 20:33:02 GMT 2023
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FDA UNII
4A04YKB3FT
Created by admin on Fri Dec 15 20:33:02 GMT 2023 , Edited by admin on Fri Dec 15 20:33:02 GMT 2023
PRIMARY
EPA CompTox
DTXSID70203389
Created by admin on Fri Dec 15 20:33:02 GMT 2023 , Edited by admin on Fri Dec 15 20:33:02 GMT 2023
PRIMARY
NSC
93138
Created by admin on Fri Dec 15 20:33:02 GMT 2023 , Edited by admin on Fri Dec 15 20:33:02 GMT 2023
PRIMARY