Galegine

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 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]

References

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

[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.

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

[1]

[2]

[3]

See also

References