Coptisine

{{chembox

| Verifiedfields = changed

| verifiedrevid = 460107369

| ImageFile=coptisine.png

| ImageSize=200px

| IUPACName=7,8,13,13a-Tetradehydro-2′H,2′′H-bis([1,3]dioxolo)[4′,5′:2,3;4′′,5′′:9,10]berbin-7-ium

| SystematicName=6,7-Dihydro-2H,10H-5λ⁵-[1,3]dioxolo[4,5-g][1,3]dioxolo[4′,5′:7,8]isoquinolino[3,2-a]isoquinolin-5-ylium

| OtherNames=

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 65268

| 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

| InChIKey = XYHOBCMEDLZUMP-UHFFFAOYAS

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=3486-66-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0GCL71VN14

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 362071

| PubChem=72322

| SMILES = O1c3c(OC1)c2c[n+]6c(cc2cc3)c5cc4OCOc4cc5CC6

}}

|Section2={{Chembox Properties

| Formula=C₁₉H₁₄NO₄+

| MolarMass=320.319

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

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Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis),{{cite journal | vauthors = Chen J, Wang F, Liu J, Lee FS, Wang X, Yang H | title = Analysis of alkaloids in Coptis chinensis Franch by accelerated solvent extraction combined with ultra performance liquid chromatographic analysis with photodiode array and tandem mass spectrometry detections | journal = Analytica Chimica Acta | volume = 613 | issue = 2 | pages = 184–95 | date = April 2008 | pmid = 18395058 | doi = 10.1016/j.aca.2008.02.060 }} greater celandine, and opium.{{cite journal |pages=198–201 |doi=10.1038/189198a0 |title=Distribution of Certain Poppy-Fumaria Alkaloids and a Possible Link with the Incidence of Glaucoma |year=1961 |last1=Hakim |first1=Sohrab A. E. |last2=Mijović |first2=Valerie |last3=Walker |first3=James |journal=Nature |volume=189 |issue=4760 |pmid=13710637}} Famous for the bitter taste that it produces, it is used in Chinese herbal medicine along with the related compound berberine for digestive disorders caused by bacterial infections.{{cite journal | vauthors = Tang J, Feng Y, Tsao S, Wang N, Curtain R, Wang Y | title = Berberine and Coptidis rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations | journal = Journal of Ethnopharmacology | volume = 126 | issue = 1 | pages = 5–17 | date = October 2009 | pmid = 19686830 | doi = 10.1016/j.jep.2009.08.009 | hdl = 10722/127599 | hdl-access = free }}