{{Chembox <!-- Images --> | ImageFile = galegine.svg | ImageSize = 200px <!-- Names --> | IUPACName = 2-(3-Methylbut-2-enyl)guanidine | OtherNames = {{ubl|Isopentenyl guanidine|Dimethylallylguanidine|Isoamylene guanidine}} <!-- Sections --> | Section1 = {{Chembox Identifiers | CASNo = 543-83-9 | PubChem = 10983 | ChemSpiderID = 10518 | ChEBI = 5265 | ChEMBL = 111469 | KEGG = C08303 | SMILES = CC(=CCN=C(N)N)C | UNII = R469KQG1EF | InChI=1S/C6H13N3/c1-5(2)3-4-9-6(7)8/h3H,4H2,1-2H3,(H4,7,8,9) | InChIKey=UVMLHMAIUVSYOL-UHFFFAOYSA-N }} | Section2 = {{Chembox Properties | C=6|H=13|N=3 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}
'''Galegine''' is a toxic chemical compound that has been isolated from ''Galega officinalis''.<ref>{{cite journal | doi = 10.1614/WS-D-10-00169.1| title = Galegine Content in Goatsrue (Galega officinalis) Varies by Plant Part and Phenological Growth Stage| journal = Weed Science| volume = 59| issue = 3| pages = 349–352| year = 2011| last1 = Oldham| first1 = Michelle| last2 = Ransom| first2 = Corey V.| last3 = Ralphs| first3 = Michael H.| last4 = Gardner| first4 = Dale R.| bibcode = 2011WeedS..59..349O}}</ref> It has also been found to be the principal cause of the toxicity of poison sedge (''Schoenus asperocarpus'').<ref>{{Cite journal | pmid = 8343085 | year = 1993 | last1 = Huxtable | first1 = C. R. | title = Identification of galegine, an isoprenyl guanidine, as the toxic principle of Schoenus asperocarpus (poison sedge) | journal = Australian Veterinary Journal | volume = 70 | issue = 5 | pages = 169–71 | last2 = Dorling | first2 = P. R. | last3 = Colegate | first3 = S. M. | doi = 10.1111/j.1751-0813.1993.tb06120.x }}</ref>
Galegine was used in the 1920s as a pharmaceutical treatment for diabetes;<ref name=Bailey>{{cite journal | doi = 10.1002/pdi.606| title = Metformin: Its botanical background| journal = Practical Diabetes International| volume = 21| issue = 3| pages = 115–117| year = 2004| last1 = Bailey| first1 = CJ| last2 = Day| first2 = C.| doi-access = free}}</ref> however, because of its toxicity, its use was soon supplanted by superior alternatives. Research on galegine eventually led to the development of metformin which is used today for treatment of type 2 diabetes.<ref name=Bailey/>
==See also== * Nitensidine D
==References== {{reflist}}
Category:Guanidine alkaloids Category:Plant toxins