Guanidinopropionic acid

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

Guanidinopropionic acid
Names
IUPAC name
3-Carbamimidamidopropanoic acid
Other names
3-(Diaminomethylideneamino)propanoic acid
Identifiers
3D model (JSmol)
3DMet
1705262
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.937
EC Number
  • 206-530-0
KEGG
MeSH guanidopropionic+acid
PubChem CID
RTECS number
  • AY3157500
UNII
  • InChI=1S/C4H9N3O2/c5-4(6)7-2-1-3(8)9/h1-2H2,(H,8,9)(H4,5,6,7) N
    Key: KMXXSJLYVJEBHI-UHFFFAOYSA-N N
SMILES
  • NC(=N)NCCC(O)=O
Properties
C4H9N3O2
Molar mass 131.135 g·mol−1
Appearance White crystals
Odor Odourless
log P −1.472
Acidity (pKa) 4.219
Basicity (pKb) 9.778
Hazards
GHS labelling:
Warning
H315, H319, H335
P261, P305+P351+P338
Related compounds
Related alkanoic acids
Related compounds
Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

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

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.

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

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