Galegine

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

Galegine

Names
IUPAC name 2-(3-Methylbut-2-enyl)guanidine
Other names Isopentenyl guanidine Dimethylallylguanidine Isoamylene guanidine
Identifiers
CAS Number	543-83-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5265
ChEMBL	ChEMBL111469
ChemSpider	10518
KEGG	C08303
PubChem CID	10983
UNII	R469KQG1EF
CompTox Dashboard (EPA)	DTXSID10202659
InChI InChI=1S/C6H13N3/c1-5(2)3-4-9-6(7)8/h3H,4H2,1-2H3,(H4,7,8,9) Key: UVMLHMAIUVSYOL-UHFFFAOYSA-N
SMILES CC(=CCN=C(N)N)C
Properties
Chemical formula	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).
Infobox references

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 based upon the effects of galegine eventually led to the development of metformin which is used today for treatment of type 2 diabetes.[3]

See also

• Nitensidine D

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. Bailey, CJ; Day, C. (2004). "Metformin: Its botanical background". Practical Diabetes International. 21 (3): 115–117. doi:10.1002/pdi.606.