Coptisine

Coptisine
IUPAC name 6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinolizinium
Identifiers
CAS number	3486-66-6 N
PubChem	72322
ChemSpider	65268 Y
ChEMBL	CHEMBL362071 Y
Jmol-3D images	{{#if:O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6|Image 1
SMILES O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6
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
Properties
Molecular formula	C19H14NO4+
Molar mass	320.319
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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.^{[citation needed]}

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.^{[citation needed]}

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