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Galegine (Molecule of the Month for November 2011)

Goat's rue, Galega officinalis



Galegine is an alkaloid is the active chemical in the plant Galega officinalis, commonly known as goat's rue, French lilac, Italian fitch or professor-weed.

Galega officinalis has been known since the Middle Ages for relieving the symptoms of diabetes mellitus. Upon analysis, it turned out to contain compounds related to guanidine, a substance that decreases blood sugar by mechanisms including a decrease in insulin resistance, but were too toxic for human use. Georges Tanret identified an alkaloid from this plant, galegine, that was less toxic, and this was evaluated in unsuccessful clinical trials in patients with diabetes in the 1920s and 1930

Other related compounds were being investigated clinically at this time, including biguanide derivatives. This work led ultimately to the discovery of metformin (Glucophage), currently recommended in international guidelines for diabetes management as the first choice for antidiabetic pharmacotherapy alongside diet and exercise, and the older agent phenformin, which has been withdrawn in most countries due to an unacceptable risk of lactic acidosis (the risk of lactic acidosis with metformin is no higher than with other antidiabetic therapies when it is prescribed according to its label). The study of galegine and related molecules in the first half of the 20th century is regarded as an important milestone in the development of oral antidiabetic pharmacotherapy.

Formal Chemical Name (IUPAC)
(3-Methylbut-2-enyl)guanidine;2-(3-methylbut-2-enyl)guanidine

References

http://en.wikipedia.org/wiki/Galega_officinalis

Picture of Galegine

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Galegine structure
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Picture of Galegine

C6H13N3



Update by Karl Harrison
(Molecule of the Month for November 2011 )