Guanidinopropionic acid

Guanidinopropionic acid

Names
IUPAC name 3-Carbamimidamidopropanoic acid[1]
Other names 3-(Diaminomethylideneamino)propanoic acid
Identifiers
CAS Number	353-09-3
3D model (Jmol)	Interactive image Interactive image
3DMet	B00534
Beilstein Reference	1705262
ChEBI	CHEBI:15968
ChEMBL	ChEMBL20489
ChemSpider	61020
ECHA InfoCard	100.005.937
EC Number	206-530-0
KEGG	C03065
MeSH	guanidopropionic+acid
PubChem	67701
RTECS number	AY3157500
InChI InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7) Key: KMXXSJLYVJEBHI-UHFFFAOYSA-N
SMILES [nH]:c(:[nH2]):[nH]CCc(:[o]):[oH] NC(=N)NCCC(O)=O
Properties
Chemical formula	C4H9N3O2
Molar mass	131.14 g·mol^−1
Appearance	White crystals
Odor	Odourless
log P	−1.472
Acidity (pKa)	4.219
Basicity (pKb)	9.778
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26, S36
Related compounds
Related alkanoic acids	Sarcosine Dimethylglycine Glycocyamine Creatine N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Arginine
Related compounds	Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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

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.