Galegine

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

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

See also

• Nitensidine D