Benzylguanidines and Other Galegine Analogues Inducing Weight Loss in Mice

G.D. Coxon, B.L. Furman, Deborah Harvey, Niall McTavish, Mark Mooney, M. Arastoo, J.M. Tettey, R.D. Waigh, Adele Kennedy

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)


Dimethylallylguanidine, also known as galegine, isolated from Galega officinalis, has been shown to have weight reducing properties in vivo. Substitution of the guanidine group with an N-cyano group and replacement of guanidine with amidine, pyrimidine, pyridine, or the imidazole moieties removed the weight reducing properties when evaluated in BALB/c mice. However, retention of the guanidine and replacement of the dimethylallyl group by a series of functionalized benzyl substituents was shown to exhibit, and in some cases significantly improve, the weight reducing properties of these molecules in BALB/c, ob/ob, and diet induced obesity (DIO) mice models. The lead compound identified, across all models, was 1-(4-chlorobenzyl)guanidine hemisulfate, which gave an average daily weight difference (% from time-matched controls; +/- SEM) of -19.7 +/- 1.0, -11.0 +/- 0.7, and -7.3 +/- 0.8 in BALB/c, ob/ob, and DIO models, respectively.
Original languageEnglish
Pages (from-to)3457-3463
Number of pages7
JournalJournal of Medicinal Chemistry
Issue number11
Publication statusPublished - 11 Jun 2009

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


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