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Coptisine: Difference between revisions

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Revision as of 10:13, 11 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit Latest revision as of 14:42, 30 April 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 399731015 | verifiedrevid = 460107369
|ImageFile=coptisine.png | ImageFile=coptisine.png
|ImageSize=200px | ImageSize=200px
|IUPACName=6,7-Dihydro-bis(1,3)benzodioxolo (5,6-a:4',5'-g)quinolizinium
| IUPACName=7,8,13,13a-Tetradehydro-2′''H'',2′′''H''-bis(dioxolo)berbin-7-ium
⚫ |OtherNames=
| SystematicName=6,7-Dihydro-2''H'',10''H''-5λ<sup>5</sup>-dioxolodioxoloisoquinolinoisoquinolin-5-ylium
⚫ |Section1= {{Chembox Identifiers
⚫ | OtherNames=
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 65268 | 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 | 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
Line 14: Line 16:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N | StdInChIKey = XYHOBCMEDLZUMP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 3486-66-6 -->
| CASNo=3486-66-6
⚫ | ChEMBL = 362071
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0GCL71VN14
| ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEMBL = 362071
| PubChem=72322 | PubChem=72322
| SMILES = O1c3c(OC1)c2c6c(cc2cc3)c5cc4OCOc4cc5CC6 | SMILES = O1c3c(OC1)c2c6c(cc2cc3)c5cc4OCOc4cc5CC6
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>19</sub>H<sub>14</sub>NO<sub>4</sub>+ | Formula=C<sub>19</sub>H<sub>14</sub>NO<sub>4</sub>+
| MolarMass=320.319 | MolarMass=320.319
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''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>
'''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.


== References==
Also found in ] and has also been detected in ].<ref>Hakim et al., 1961</ref> {{Fact|date=September 2008}}

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.

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>.

==Footnotes==
{{reflist}} {{reflist}}


] ]
]

]


{{organic-compound-stub}} {{alkaloid-stub}}

Latest revision as of 14:42, 30 April 2023

Coptisine
Names
IUPAC name 7,8,13,13a-Tetradehydro-2′H,2′′H-bis(dioxolo)berbin-7-ium
Systematic IUPAC name 6,7-Dihydro-2H,10H-5λ-dioxolodioxoloisoquinolinoisoquinolin-5-ylium
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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+1Key: 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+1Key: XYHOBCMEDLZUMP-UHFFFAOYAS
SMILES
  • O1c3c(OC1)c2c6c(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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis), greater celandine, and opium. 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.

References

  1. Chen J, Wang F, Liu J, Lee FS, Wang X, Yang H (April 2008). "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". Analytica Chimica Acta. 613 (2): 184–95. doi:10.1016/j.aca.2008.02.060. PMID 18395058.
  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. Tang J, Feng Y, Tsao S, Wang N, Curtain R, Wang Y (October 2009). "Berberine and Coptidis rhizoma as novel antineoplastic agents: a review of traditional use and biomedical investigations". Journal of Ethnopharmacology. 126 (1): 5–17. doi:10.1016/j.jep.2009.08.009. hdl:10722/127599. PMID 19686830.
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