3-Guanidinopropionic acid

CHF 30.00
In stock
AG-CR1-3678-M500500 mgCHF 30.00
AG-CR1-3678-G0011 gCHF 55.00
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Product Details
Synonyms β-GPA; PNU 10483; N-(Aminoiminomethyl)-β-alanine
Product Type Chemical
Properties
Formula

C4H9N3O2

MW 131.1
CAS 353-09-3
RTECS AY3157500
Purity Chemicals ≥98%
Appearance White powder.
Solubility Soluble in water (50mg/ml) or other aqueous buffers (e.g. PBS).
InChi Key KMXXSJLYVJEBHI-UHFFFAOYSA-N
Smiles NC(NCCC(O)=O)=N
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Aqueous solutions should not be stored for longer than one day.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Store solutions at -20°C in the dark.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Competitive creatine uptake inhibitor.
  • Creatine analog that alters skeletal muscle energy expenditure.
  • Thermogenesis inhibitor. Inhibitor of energy expenditure through reduction of ATP.
  • AMPK stimulator and PGC-1α activator. Reduces cellular ATP, creatine and phosphocreatine levels, consequently stimulating AMP-activated protein kinase (AMPK) and activating PPARγ coactivator 1α (PGC-1α).
  • Evokes a shift from glycolytic to oxidative metabolism, increased cellular glucose uptake and increased fatigue tolerance.
  • Ameliorates hyperglycemia in animal models of non-insulin-dependent diabetes (NIDDM). Improved insulin sensitivity and promoted weight loss selectively from adipose tissue.
  • Studied for potential use during protein refolding as an anti-aggregatory molecule similar to L-arginine.
Product References
  1. Energy metabolism of skeletal muscle containing cyclocreatine phosphate. Delay in onset of rigor mortis and decreased glycogenolysis in response to ischemia or epinephrine: T.M. Annesley & J.B. Walker; J. Biol. Chem. 255, 3924 (1980)
  2. Biochemical adaptation in the skeletal muscle of rats depleted of creatine with the substrate analogue β-guanidinopropionic acid: E.A. Shoubridge, et al.; Biochem. J. 232, 125 (1985)
  3. Antihyperglycemic action of guanidinoalkanoic acids: 3-guanidinopropionic acid ameliorates hyperglycemia in diabetic KKAy and C57BL6Job/ob mice and increases glucose disappearance in rhesus monkeys: M.D. Meglasson, et al.; J. Pharmacol. Exp. Ther. 266, 1454 (1993)
  4. Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent: S.D. Larsen, et al.; J. Med. Chem. 44, 1217 (2001)
  5. Aging-associated reductions in AMP-activated protein kinase activity and mitochondrial biogenesis: R.M. Reznick, et al.; Cell Metab. 5, 151 (2007)
  6. Impaired PGC-1α function in muscle in Huntington's disease: R.K. Chaturvedi, et al.; Hum. Mol. Gen. 18, 3048 (2009)
  7. The effect of the creatine analogue beta-guanidinopropionic acid on energy metabolism: a systematic review: I. Oudman, et al.; PLoS One 8, e52879 (2013) (Review)
  8. Genetic depletion of adipocyte creatine metabolism inhibits diet-induced thermogenesis and drives obesity: L. Kazak, et al.; Cell Metab. 26, 660 (2017)
  9. Creatine fuels the thermic effect of feeding: A.R. Saltiel; Cell Metab. 26, 594 (2017) (Review)
  10. β-GPA treatment leads to elevated basal metabolic rate and enhanced hypoxic exercise tolerance in mice: T.T. Ross, et al.; Physiol. Rep. 5, e13192 (2017)
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