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
3D model (Jmol)	Interactive image
ChEMBL	ChEMBL362071
ChemSpider	65268
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 Key: XYHOBCMEDLZUMP-UHFFFAOYSA-N 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).
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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

1. Complementary and Alternative Healing University (Chinese Medicine)
2. Hakim, Sohrab A. E.; Mijović, Valerie; Walker, James (1961). "Distribution of Certain Poppy-Fumaria Alkaloids and a Possible Link with the Incidence of Glaucoma". Nature. 189 (4760): 198–201. doi:10.1038/189198a0. PMID 13710637.
3. Ro, Jai Seup; Lee, Sang Seon; Lee, Kyong Soon; Lee, Myung Koo (2001). "Inhibition of type a monoamine oxidase by coptisine in mouse brain". Life Sciences. 70 (6): 639–45. doi:10.1016/S0024-3205(01)01437-0. PMID 11833714.
4. Colombo, Maria Laura; Bugatti, Carlo; Mossa, Andrea; Pescalli, Nicoletta; Piazzoni, Laura; Pezzoni, Gabriella; Menta, Ernesto; Spinelli, Silvano; et al. (2001). "Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine". Il Farmaco. 56 (5–7): 403–9. doi:10.1016/S0014-827X(01)01121-1. PMID 11482767.