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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[1]
Other names
3-(Diaminomethylideneamino)propanoic acid[citation needed]
Identifiers
  • 353-09-3 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00534
1705262
ChEBI
  • CHEBI:15968 N
ChEMBL
  • ChEMBL20489 N
ChemSpider
  • 61020 N
ECHA InfoCard 100.005.937
EC Number
  • 206-530-0
KEGG
  • C03065 N
MeSH guanidopropionic+acid
  • 67701
RTECS number
  • AY3157500
UNII
  • UL1984YRKA Y
  • DTXSID40188795
  • 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
  • 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 ?)

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". American Journal of Physiology. Endocrinology and Metabolism. 281 (6): E1340–E1346. doi:10.1152/ajpendo.2001.281.6.e1340. PMID 11701451. S2CID 21577702.
  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.

guanidinopropionic, acid, also, referred, guanidinopropionic, acid, beta, guanidinopropionic, acid, dietary, supplement, names, iupac, name, carbamimidamidopropanoic, acid, other, names, diaminomethylideneamino, propanoic, acid, citation, needed, identifiers, . b Guanidinopropionic acid also referred to as guanidinopropionic acid beta guanidinopropionic acid or b GPA is a dietary supplement Guanidinopropionic acid Names IUPAC name 3 Carbamimidamidopropanoic acid 1 Other names 3 Diaminomethylideneamino propanoic acid citation needed Identifiers CAS Number 353 09 3 Y 3D model JSmol Interactive image 3DMet B00534 Beilstein Reference 1705262 ChEBI CHEBI 15968 N ChEMBL ChEMBL20489 N ChemSpider 61020 N ECHA InfoCard 100 005 937 EC Number 206 530 0 KEGG C03065 N MeSH guanidopropionic acid PubChem CID 67701 RTECS number AY3157500 UNII UL1984YRKA Y CompTox Dashboard EPA DTXSID40188795 InChI InChI 1S C4H9N3O2 c5 4 6 7 2 1 3 8 9 h1 2H2 H 8 9 H4 5 6 7 NKey KMXXSJLYVJEBHI UHFFFAOYSA N N SMILES NC N NCCC O O Properties Chemical formula C 4H 9N 3O 2 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 Pictograms Signal word Warning Hazard statements H315 H319 H335 Precautionary statements P261 P305 P351 P338 Related compounds Related alkanoic acids SarcosineDimethylglycineGlycocyamineCreatineN Methyl D aspartic acidbeta Methylamino L alanineArginine 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 Y N Infobox references b 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 b GPA can ameliorate hyperglycemia in animal models of noninsulin dependent diabetes 3 Though the oral availability of b GPA is well established the basic uptake mechanism has not been studied yet 4 References edit 3 guanidinopropanoic acid CHEBI 15968 Chemical Entities of Biological Interest UK European Bioinformatics Institute 20 July 2010 Main Retrieved 26 April 2012 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 American Journal of Physiology Endocrinology and Metabolism 281 6 E1340 E1346 doi 10 1152 ajpendo 2001 281 6 e1340 PMID 11701451 S2CID 21577702 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 Metzner L Dorn M Markwardt F Brandsch M April 2009 The Orally Active Antihyperglycemic Drug b 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 Retrieved from https en wikipedia org w index php title Guanidinopropionic acid amp oldid 1152070935, wikipedia, wiki, book, books, library,

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