- Coptisine
-
Coptisine 
6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinoliziniumIdentifiers CAS number 3486-66-6 
PubChem 72322 ChemSpider 65268 
ChEMBL CHEMBL362071 Jmol-3D images Image 1 - O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6
- 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
Properties Molecular formula C19H14NO4+ Molar mass 320.319 
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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
- ^ Complementary and Alternative Healing University (Chinese Medicine)[unreliable medical source?]
- ^ 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.
- ^ 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.
- ^ 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.
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