Guanidinopropionic acid

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Guanidinopropionic acid
Identifiers
CAS number353-09-3 YesY
PubChem67701
ChemSpider61020 YesY
EC number206-530-0
KEGGC03065 YesY
MeSHguanidopropionic+acid
ChEBICHEBI:15968 YesY
ChEMBLCHEMBL20489 YesY
RTECS numberAY3157500
Beilstein Reference1705262
3DMetB00534
Jmol-3D imagesImage 1
Image 2
Properties
Molecular formulaC4H9N3O2
Molar mass131.13 g mol−1
AppearanceWhite crystals
OdorOdourless
log P−1.472
Acidity (pKa)4.219
Basicity (pKb)9.778
Hazards
GHS pictogramsThe exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordWARNING
GHS hazard statementsH315, H319, H335
GHS precautionary statementsP261, P305+351+338
EU classificationIrritant Xi
R-phrasesR36/37/38
S-phrasesS26, S36
Related compounds
Related alkanoic acids
Related compoundsDimethylacetamide
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references
 
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Guanidinopropionic acid
Identifiers
CAS number353-09-3 YesY
PubChem67701
ChemSpider61020 YesY
EC number206-530-0
KEGGC03065 YesY
MeSHguanidopropionic+acid
ChEBICHEBI:15968 YesY
ChEMBLCHEMBL20489 YesY
RTECS numberAY3157500
Beilstein Reference1705262
3DMetB00534
Jmol-3D imagesImage 1
Image 2
Properties
Molecular formulaC4H9N3O2
Molar mass131.13 g mol−1
AppearanceWhite crystals
OdorOdourless
log P−1.472
Acidity (pKa)4.219
Basicity (pKb)9.778
Hazards
GHS pictogramsThe exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal wordWARNING
GHS hazard statementsH315, H319, H335
GHS precautionary statementsP261, P305+351+338
EU classificationIrritant Xi
R-phrasesR36/37/38
S-phrasesS26, S36
Related compounds
Related alkanoic acids
Related compoundsDimethylacetamide
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 July2010. 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.