Guanidinopropionic acid

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Guanidinopropionic acid
Skeletal formula of a guanidinopropionic acid minor tautomer
Names
IUPAC name
3-Carbamimidamidopropanoic acid[1]
Other names
3-(Diaminomethylideneamino)propanoic acid[citation needed]
Identifiers
3DMet B00534
1705262
353-09-3 YesY
ChEBI CHEBI:15968 N
ChEMBL ChEMBL20489 N
ChemSpider 61020 N
EC number 206-530-0
Jmol-3D images Image
Image
KEGG C03065 N
MeSH guanidopropionic+acid
PubChem 67701
RTECS number AY3157500
Properties
C4H9N3O2
Molar mass 131.13 g·mol−1
Appearance White crystals
Odor Odourless
log P −1.472
Acidity (pKa) 4.219
Basicity (pKb) 9.778
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H315, H319, H335
P261, P305+351+338
EU classification Irritant Xi
R-phrases R36/37/38
S-phrases S26, S36
Related compounds
Related alkanoic acids
Related compounds
Dimethylacetamide
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

β-Guanidinopropionic acid, also referred to as guanidinopropionic acid, beta-guanidinopropionic acid or β-GPA, is a dietary supplement.

β-Guanidinopropionic acid is a white crystalline powder soluble in water (50 mg/ml-clear, colorless solution).[2]

Studies on animals (rats, monkeys, hamsters) show that acidic guanidine derivatives such as β-GPA can ameliorate hyperglycemia in animal models of noninsulin-dependent diabetes.[3]

Though the oral availability of β-GPA is well established, the basic uptake mechanism has not been studied yet.[4]

References[edit]

  1. ^ "3-guanidinopropanoic acid (CHEBI:15968)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 July 2010. Main. Retrieved 26 April 2012. 
  2. ^ Bergeron, R.; Ren, J. M.; Cadman, K. S.; Moore, I. K.; Perret, P.; Pypaert, M.; Young, L. H.; Semenkovich, C. F.; Shulman, G. I. (2001). "Chronic Activation of AMP Kinase Results in NRF-1 Activation and Mitochondrial Biogenesis" (pdf). American Journal of Physiology. Endocrinology and Metabolism 281 (6): E1340–E1346. PMID 11701451. 
  3. ^ Meglasson, M. D.; Wilson, J. M.; Yu, J. H.; Robinson, D. D.; Wyse, B. M.; de Souza, C. J. (September 1993). "Antihyperglycemic Action of Guanidinoalkanoic Acids: 3-Guanidinopropionic Acid Ameliorates Hyperglycemia in Diabetic KKAy and C57BL6Job/ob Mice and Increases Glucose Disappearance in Rhesus Monkeys". The Journal of Pharmacology and Experimental Therapeutics 266 (3): 1454–1462. PMID 8371149. 
  4. ^ Metzner, L.; Dorn, M.; Markwardt, F.; Brandsch, M. (April 2009). "The Orally Active Antihyperglycemic Drug β-Guanidinopropionic Acid is Transported by the Human Proton-Coupled Amino Acid Transporter hPAT1". Molecular Pharmaceutics 6 (3): 1006–1011. doi:10.1021/mp9000684. PMID 19358571.