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{{chembox|Verifiedfields = changed|Watchedfields = changed|verifiedrevid = 415511050|Name = Gramine|PIN = 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine|OtherNames = donaxine

correct|??}}|ImageFile = Gramine Structure.png|ImageSize = 150px|ImageName = Chemical structure of gramine|Section1={{Chembox Identifiers

correct|chemspider}}|ChemSpiderID = 6625

correct|EBI}} |ChEBI = 28948

correct|kegg}}|KEGG = C08304|InChI = 1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3|InChIKey = OCDGBSUVYYVKQZ-UHFFFAOYAK

correct|EBI}}|ChEMBL = 254348|PubChem = 6890|EC_number = 201-749-8|UNII = FGQ8A78L14

correct|chemspider}}|StdInChI = 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3

correct|chemspider}}|StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N

correct|??}}|CASNo = 87-52-5|SMILES = c1cccc2c1c(c[nH]2)CN(C)C}}|Section2={{Chembox Properties|Formula = C11H14N2|MolarMass = 174.24 g/mol|MeltingPtC = 138 to 139}}|Section7={{Chembox Hazards| NFPA-H = 2| NFPA-R = 0| NFPA-F = 1}}}}Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.JOURNAL, Corcuera, L. J., Biochemical Basis of the Resistance of the Barley to Aphids, Phytochemistry (journal), Phytochemistry, 1993, 33, 4, 741–747, 10.1016/0031-9422(93)85267-U, Occurrence Gramine has been found in the giant reed, Arundo donax,JOURNAL, Ãœber die Alkaloide von Arundo Donax L., Orechoff, A., Norkina, S., Berichte der Deutschen Chemischen Gesellschaft, 1935, 68, 3, 436–437, 10.1002/cber.19350680312, Acer saccharinum (Silver Maple),JOURNAL, Pachter, I. J., Zacharias, D. E., Ribeiro, O., Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis, Journal of Organic Chemistry, 1959, 24, 9, 1285–1287, 10.1021/jo01091a032, Hordeum, (a grass genus that includes barley) and PhalarisBOOK, Toxicants of Plant Origin, Alkaloids, 172, Cheeke, P. R., CRC Press, 1989, 0-8493-6990-8,weblink (another grass genus). Effects and toxicity Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).JOURNAL, Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z, Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay, PLOS ONE, 8, 5, e63354, 2013, 23691032, 3653934, 10.1371/journal.pone.0063354, 2013PLoSO...863354S, free, The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.JOURNAL, Erspamer, V., Pharmacology of Indolealkylamines, Pharmacological Reviews, 1954, 6, 4, 425–487, 13236482,weblink 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.JOURNAL, Corcuera, L. J., Effects of Indole Alkaloids from Gramineae on Aphids, Phytochemistry, 1984, 23, 3, 539–541, 10.1016/S0031-9422(00)80376-3, References {{Reflist}}