| Revision as of 14:42, 17 August 2011 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits CAS#← Previous edit |
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{{orphan|date=August 2009}} |
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{{Chembox |
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{{Chembox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 381289752 |
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| verifiedrevid = 445341112 |
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| ImageFile = Complanine structure.svg |
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| ImageFile = Complanine structure.svg |
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| ImageSize = 250px |
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| ImageSize = 250px |
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| PIN = 4-{amino}-''N'',''N'',''N''-trimethyl-4-oxobutan-1-aminium |
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| IUPACName = |
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| OtherNames = (−)-Complanine |
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| OtherNames = {{ubl | (−)-Complanine | (''R'')-(−)-Complanine }} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 1042688-43-6 |
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| CASNo = 1042688-43-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = |
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| SMILES = }} |
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| UNII = BXC744Y6CF |
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| PubChem = 24887668 |
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| Section2 = {{Chembox Properties |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| C=11|H=22|N=1|O=1 |
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| ChemSpiderID = 25047857 |
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| MolarMass = |
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| SMILES = CC/C=C\C/C=C\CC(CNC(=O)CCC(C)(C)C)O |
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| Appearance = |
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| InChI = 1/C18H34N2O2/c1-5-6-7-8-9-10-11-13-17(21)16-19-18(22)14-12-15-20(2,3)4/h6-7,9-10,17,21H,5,8,11-16H2,1-4H3/p+1/b7-6-,10-9-/t17-/m1/s1 |
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| Density = |
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| InChIKey = QYFDYRHORFAECH-SKOIHYTMBD |
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| MeltingPt = |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| BoilingPt = |
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| StdInChI = 1S/C18H34N2O2/c1-5-6-7-8-9-10-11-13-17(21)16-19-18(22)14-12-15-20(2,3)4/h6-7,9-10,17,21H,5,8,11-16H2,1-4H3/p+1/b7-6-,10-9-/t17-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = QYFDYRHORFAECH-SVCKQPKZSA-O }} |
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|Section2={{Chembox Properties |
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| C=11 | H=22 | N=1 | O=1 |
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| Formula_Charge = + |
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| Appearance = |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = }} |
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| AutoignitionPt = }} |
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}} |
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'''Complanine''' is a natural product isolated from the marine ] ''Eurythoe complanata''. |
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'''Complanine''' is a ] isolated from the marine ] '']''. It causes an inflammatory effect upon contact with the skin or mucous membranes. |
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== Occurrence == |
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== Occurrence == |
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It was known that the fireworm ''Eurythoe complanata'' are dangerous for ]s and ]s because of there ]-inducing effect. In humans it takes effect by harming with small setae and causes inflammation of the skin. Complanine was the first compound isolated from the fireworm which causes the same effects. The chemical structure was determined by spectroscopical methods<ref>{{cite journal | author = Kazuhiko Nakamura, Yu Tachikawa, Makoto Kitamura, Osamu Ohno, Masami Suganuma and Daisuke Uemura | title = Complanine, an inflammation-inducing substance isolated from the marine fireworm Eurythoe complanata | journal = Org. Biomol. Chem. | year = 2008 | volume = 6 | pages = 2058–2060 | doi = 10.1039/b803107j | pmid = 18528565 | issue = 12}}</ref> and the absolute configuration was confirmed with a total synthesis.<ref>{{cite journal | doi = 10.3762/bjoc.5.12 | url = http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-5-12&vt=f&bpn=home | title = (−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study | year = 2009 | last1 = Nakamura | first1 = Kazuhiko | last2 = Tachikawa | first2 = Yu | last3 = Uemura | first3 = Daisuke | journal = Beilstein Journal of Organic Chemistry | volume = 5}}</ref> |
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It was previously known that handling the fireworm caused it to release a chemical that induces ] of the skin of marine predators and mammals (including humans). Complanine was the first compound isolated from the fireworm which causes these effects. The chemical structure of Complanine was determined by spectroscopical methods<ref>{{cite journal |author1=Kazuhiko Nakamura |author2=Yu Tachikawa |author3=Makoto Kitamura |author4=Osamu Ohno |author5=Masami Suganuma |author6=Daisuke Uemura | title = Complanine, an inflammation-inducing substance isolated from the marine fireworm Eurythoe complanata | journal = Org. Biomol. Chem. | year = 2008 | volume = 6 | pages = 2058–2060 | doi = 10.1039/b803107j | pmid = 18528565 | issue = 12}}</ref> and the absolute configuration was confirmed with a total synthesis.<ref>{{cite journal | doi = 10.3762/bjoc.5.12 | url = http://www.beilstein-journals.org/bjoc/single/articleFullText.htm?publicId=1860-5397-5-12&vt=f&bpn=home | title = (−)-Complanine, an inflammatory substance of marine fireworm: a synthetic study | year = 2009 | last1 = Nakamura | first1 = Kazuhiko | last2 = Tachikawa | first2 = Yu | last3 = Uemura | first3 = Daisuke | journal = Beilstein Journal of Organic Chemistry | volume = 5|page = 12|pmid = 19478919| pmc = 2686394 }}</ref> |
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It is presumed that this compound has a deterring affect on predators of the fireworm. |
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It is presumed that this compound's function is to deter predators of the fireworm. |
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== References == |
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== References == |
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