Coptisine

Coptisine

Names
IUPAC name 6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinolizinium
Identifiers
CAS Number	3486-66-6 N
ChEMBL	ChEMBL362071 Y
ChemSpider	65268 Y
Jmol interactive 3D	Image
PubChem	72322
InChI InChI=1S/C19H14NO4/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/q+1 Y Key: XYHOBCMEDLZUMP-UHFFFAOYSA-N Y InChI=1/C19H14NO4/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/q+1 Key: XYHOBCMEDLZUMP-UHFFFAOYAS
SMILES O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6
Properties
Chemical formula	C19H14NO4+
Molar mass	320.319
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis).^[1] Famous for the bitter taste that it produces, it is used in Chinese herbal medicine along with the related compound berberine for treating digestive disorders caused by bacterial infections.

Also found in Greater Celandine and has also been detected in Opium.^[2]

Coptisine has been found to reversibly inhibit Monoamine oxidase A in mice, pointing to a potential role as a natural antidepressant.^[3] However, this may also imply a hazard for those taking other medications or with a natural functional disorder in Monoamine oxidase A.

Coptisine was found to be toxic to larval brine shrimp and a variety of human cell lines, potentially implying a therapeutic effect on cancer or alternatively a generally toxic character. The same authors illustrate a four-step process to produce Coptisine from Berberine.^[4]

Footnotes