| Revision as of 15:01, 30 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← Previous edit |
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{{chembox |
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{{chembox |
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|ImageFile=coptisine.png |
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| verifiedrevid = 460107369 |
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|ImageSize=200px |
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| ImageFile=coptisine.png |
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|IUPACName=6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinolizinium |
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|OtherNames= |
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| IUPACName=7,8,13,13a-Tetradehydro-2′''H'',2′′''H''-bis(dioxolo)berbin-7-ium |
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|Section1= {{Chembox Identifiers |
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| SystematicName=6,7-Dihydro-2''H'',10''H''-5λ<sup>5</sup>-dioxolodioxoloisoquinolinoisoquinolin-5-ylium |
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| ChemSpiderID = 65268 |
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| OtherNames= |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 65268 |
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| 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 |
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| 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 |
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| InChIKey = XYHOBCMEDLZUMP-UHFFFAOYAS |
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| InChIKey = XYHOBCMEDLZUMP-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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 |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N |
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| StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=3486-66-6 |
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| CASNo=3486-66-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=72322 |
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| UNII = 0GCL71VN14 |
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| SMILES = O1c3c(OC1)c2c6c(cc2cc3)c5cc4OCOc4cc5CC6 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 362071 |
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| PubChem=72322 |
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| SMILES = O1c3c(OC1)c2c6c(cc2cc3)c5cc4OCOc4cc5CC6 |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>19</sub>H<sub>14</sub>NO<sub>4</sub>+ |
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| Formula=C<sub>19</sub>H<sub>14</sub>NO<sub>4</sub>+ |
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| MolarMass=320.319 |
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| MolarMass=320.319 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Coptisine''' is an ] found in Chinese goldthread ('']''),<ref name="pmid18395058">{{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 }}</ref> ], and opium.<ref>{{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}}</ref> Famous for the bitter taste that it produces, it is used in ] along with the related compound ] for digestive disorders caused by bacterial infections.<ref name="pmid19686830">{{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 }}</ref> |
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'''Coptisine''' is an ] found in Chinese goldthread ('']'').<ref></ref> Famous for the bitter taste that it produces, it is used in ] along with the related compound ] for treating digestive disorders caused by bacterial infections. |
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== References== |
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Also found in ] and has also been detected in ].<ref>Hakim et al., 1961</ref> {{Fact|date=September 2008}} |
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Coptisine has been found to reversibly inhibit ] in mice, pointing to a potential role as a natural antidepressant<ref></ref>. However, this may also imply a hazard for those taking other medications or with a natural functional disorder in Monoamine oxidase A. |
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Coptisine was found to be toxic to larval ] 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 ]<ref></ref>. |
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==Footnotes== |
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{{reflist}} |
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{{organic-compound-stub}} |
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{{alkaloid-stub}} |