Galegine

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Galegine
Names
IUPAC name
2-(3-Methylbut-2-enyl)guanidine
Other names
  • Isopentenyl guanidine
  • Dimethylallylguanidine
  • Isoamylene guanidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C6H13N3/c1-5(2)3-4-9-6(7)8/h3H,4H2,1-2H3,(H4,7,8,9)
    Key: UVMLHMAIUVSYOL-UHFFFAOYSA-N
  • CC(=CCN=C(N)N)C
Properties
C6H13N3
Molar mass 127.191 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Galegine is a toxic chemical compound that has been isolated from Galega officinalis.[1] It has also been found to be the principal cause of the toxicity of poison sedge (Schoenus asperocarpus).[2]

Galegine was used in the 1920s as a pharmaceutical treatment for diabetes;[3] 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.[3]

See also

References

  1. ^ Oldham, Michelle; Ransom, Corey V.; Ralphs, Michael H.; Gardner, Dale R. (2011). "Galegine Content in Goatsrue (Galega officinalis) Varies by Plant Part and Phenological Growth Stage". Weed Science. 59 (3): 349–352. doi:10.1614/WS-D-10-00169.1.
  2. ^ Huxtable, C. R.; Dorling, P. R.; Colegate, S. M. (1993). "Identification of galegine, an isoprenyl guanidine, as the toxic principle of Schoenus asperocarpus (poison sedge)". Australian Veterinary Journal. 70 (5): 169–71. doi:10.1111/j.1751-0813.1993.tb06120.x. PMID 8343085.
  3. ^ a b Bailey, CJ; Day, C. (2004). "Metformin: Its botanical background". Practical Diabetes International. 21 (3): 115–117. doi:10.1002/pdi.606.
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