| Revision as of 14:16, 23 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 400101348 |
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|Watchedfields = changed |
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| Name = Gramine |
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|verifiedrevid = 415511050 |
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| IUPACName = 3-(dimethylamino<br />methyl)-indole |
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| ImageFile = Gramine Structure.png |
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|Name = Gramine |
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|PIN = 1-(1''H''-Indol-3-yl)-''N'',''N''-dimethylmethanamine |
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<!-- | ImageSize = 150px --> |
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|OtherNames = donaxine |
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| ImageName = Chemical structure of gramine |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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|ImageFile = Gramine Structure.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ImageSize = 150px |
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| ChemSpiderID = 6625 |
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|ImageName = Chemical structure of gramine |
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| KEGG = C08304 |
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|Section1={{Chembox Identifiers |
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| InChI = 1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = OCDGBSUVYYVKQZ-UHFFFAOYAK |
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|ChemSpiderID = 6625 |
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| ChEMBL = 254348 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEBI = 28948 |
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| StdInChI = 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|KEGG = C08304 |
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| StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N |
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|InChI = 1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
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| CASNo = 87-52-5 |
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|InChIKey = OCDGBSUVYYVKQZ-UHFFFAOYAK |
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| SMILES = c1cccc2c1c(cn2)CN(C)C |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 254348 |
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|PubChem = 6890 |
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|EC_number = 201-749-8 |
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|UNII = FGQ8A78L14 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI = 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|??}} |
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|CASNo = 87-52-5 |
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|SMILES = c1cccc2c1c(c2)CN(C)C |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>11</sub>H<sub>14</sub>N<sub>2</sub> |
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|Formula = C<sub>11</sub>H<sub>14</sub>N<sub>2</sub> |
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| MolarMass = 174.24 g/mol |
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|MolarMass = 174.24 g/mol |
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|MeltingPtC = 138 to 139 |
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| MeltingPt = 138-139 °C |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| NFPA-H = 2 |
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| NFPA-H = 2 |
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| NFPA-R = 0 |
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| NFPA-R = 0 |
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| NFPA-F = 1}} |
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| NFPA-F = 1}} |
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'''Gramine''' (also called donaxine) is a naturally occurring ] ] present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.<ref>{{cite journal | doi = 10.1016/0031-9422(93)85267-U | author = Corcuera, L. J. | title = Biochemical basis of the resistance of the barley to aphids | journal = ] | year = 1993 | volume = 33 | pages = 741–747}}</ref> |
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'''Gramine''' (also called '''donaxine''') is a naturally occurring ] ] present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.<ref name=barley>{{cite journal | author = Corcuera, L. J. | title = Biochemical Basis of the Resistance of the Barley to Aphids | journal = ] | year = 1993 | volume = 33 | issue = 4 | pages = 741–747 | doi = 10.1016/0031-9422(93)85267-U}}</ref> |
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==Occurrence== |
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==Occurrence== |
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Gramine has been found in the '']'',<ref>{{cite journal | title = Über die Alkaloide von Arundo Donax L. | author = A. Orechoff, S. Norkina | journal = ] | year = 1935 | volume = 68 | issue = 3 | pages = 436–437 | doi = 10.1002/cber.19350680312}}</ref> ],<ref> |
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Gramine has been found in the giant reed, '']'',<ref>{{cite journal | title = Über die Alkaloide von ''Arundo Donax'' L. |author1=Orechoff, A. |author2=Norkina, S. | journal = ] | year = 1935 | volume = 68 | issue = 3 | pages = 436–437 | doi = 10.1002/cber.19350680312}}</ref><ref name=toxicants/> '']'' (]),<ref>{{cite journal |author1=Pachter, I. J. |author2=Zacharias, D. E. |author3=Ribeiro, O. | title = Indole Alkaloids of ''Acer saccharinum'' (the Silver Maple), ''Dictyoloma incanescens'', ''Piptadenia colubrina'', and ''Mimosa hostilis'' | journal = ] | year = 1959 | volume = 24 | issue = 9 | pages = 1285–1287 | doi = 10.1021/jo01091a032}}</ref> '']'',<ref name=barley/><ref name=toxicants/> (a grass genus that includes barley) and '']''<ref name=toxicants>{{cite book | title = Toxicants of Plant Origin, Alkaloids | page = 172 | author = Cheeke, P. R. | publisher = CRC Press | year = 1989 | isbn = 0-8493-6990-8 | url = https://books.google.com/books?id=eASgQyXq8xMC&pg=PA172}}</ref> (another grass genus). |
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{{cite journal | journal = ] | year = 1959 | volume = 24 | pages = 1285 | doi = 10.1021/jo01091a032 | title = Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis | author = Irwin J. Pachter, David E. Zacharias, Oscar Ribeiro }}</ref> '']'', and '']'' plant species. |
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==Effects and toxicity== |
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==Synthesis== |
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Gramine has been found to act as an ] of the ] (AdipoR1).<ref name="pmid23691032">{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354| bibcode = 2013PLoSO...863354S | doi-access = free }}</ref> |
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Despite being widely available in several plant species, gramine is far easier to synthesize directly from indole via a ] with ] and ]. |
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The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.<ref>{{cite journal | author = Erspamer, V. | title = Pharmacology of Indolealkylamines | journal = Pharmacological Reviews | year = 1954 | volume = 6 | issue = 4 | pages = 425–487 | pmid = 13236482 | url = http://pharmrev.aspetjournals.org/content/6/4/425.abstract}}</ref> |
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Numerous studies have been done on the toxicity of gramine to insects harmful to crops in order to assess its potential use as an insecticide.<ref>{{cite journal | author = Corcuera, L. J. | title = Effects of Indole Alkaloids from Gramineae on Aphids | journal = Phytochemistry | year = 1984 | volume = 23 | issue = 3 | pages = 539–541 | doi = 10.1016/S0031-9422(00)80376-3}}</ref> |
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==Uses== |
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Gramine is used mostly in ] ] as a starting material for ] syntheses. |
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All reactions of gramine follow the same general reaction scheme. Gramine is reacted with a strong ], such as ], to form the quaternary ammonium salt '''2'''. The ammonium salt will undergo a ] or ] to give the very active intermediate '''3''', which can accept a wide range of ]s to give the desired product '''4'''. |
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==References== |
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==References== |
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{{Reflist}} |
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