MedKoo Cat#: 597233 | Name: Guanidinoglutaric acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Guanidinoglutaric acid is a nitric oxide synthase inhibitor.

Chemical Structure

Guanidinoglutaric acid
Guanidinoglutaric acid
CAS#73477-53-9

Theoretical Analysis

MedKoo Cat#: 597233

Name: Guanidinoglutaric acid

CAS#: 73477-53-9

Chemical Formula: C6H11N3O4

Exact Mass: 189.0750

Molecular Weight: 189.17

Elemental Analysis: C, 38.10; H, 5.86; N, 22.21; O, 33.83

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 600.00 2 Weeks
100mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
Guanidinoglutaric acid; GGA; (S)-(-)-2-Guanidinoglutaric Acid; alpha-guanidinoglutaric acid; N-Amidino-L-glutamate;
IUPAC/Chemical Name
carbamimidoyl-L-glutamic acid
InChi Key
RHVVRMJOHATSPD-VKHMYHEASA-N
InChi Code
InChI=1S/C6H11N3O4/c7-6(8)9-3(5(12)13)1-2-4(10)11/h3H,1-2H2,(H,10,11)(H,12,13)(H4,7,8,9)/t3-/m0/s1
SMILES Code
O=C(O)CC[C@@H](C(O)=O)NC(N)=N
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 189.17 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Tachikawa M, Hosoya K. Transport characteristics of guanidino compounds at the blood-brain barrier and blood-cerebrospinal fluid barrier: relevance to neural disorders. Fluids Barriers CNS. 2011 Feb 28;8(1):13. doi: 10.1186/2045-8118-8-13. PubMed PMID: 21352605; PubMed Central PMCID: PMC3058069. 2: Burov S, Moskalenko Y, Dorosh M, Shkarubskaya Z, Panarin E. Incorporation of N-amidino-pyroglutamic acid into peptides using intramolecular cyclization of alpha-guanidinoglutaric acid. J Pept Sci. 2009 Nov;15(11):760-6. doi: 10.1002/psc.1171. PubMed PMID: 19739127. 3: Hiramatsu M. A role for guanidino compounds in the brain. Mol Cell Biochem. 2003 Feb;244(1-2):57-62. Review. PubMed PMID: 12701810. 4: Cordelier P, Estève JP, Rivard N, Marletta M, Vaysse N, Susini C, Buscail L. The activation of neuronal NO synthase is mediated by G-protein betagamma subunit and the tyrosine phosphatase SHP-2. FASEB J. 1999 Nov;13(14):2037-50. PubMed PMID: 10544187. 5: Hiramatsu M, Komatsu M. Measurement of hydroxyl radical by salicylate in striatum of intact brain. Methods Enzymol. 1999;300:252-5. PubMed PMID: 9919528. 6: Habu H, Yokoi I, Kabuto H, Willmore LJ, Mori A. Seizures induced by alpha-guanidinoglutaric acid, a nitric oxide synthase inhibitor, are controlled by L-arginine. Biochem Mol Biol Int. 1996 May;39(1):87-95. PubMed PMID: 8799331. 7: Mori A, Kohno M, Masumizu T, Packer L. alpha-Guanidinoglutaric acid as a free radical generator. Biochem Mol Biol Int. 1995 Oct;37(2):371-4. PubMed PMID: 8673021. 8: Yokoi I, Kabuto H, Habu H, Inada K, Toma J, Mori A. Structure-activity relationships of arginine analogues on nitric oxide synthase activity in the rat brain. Neuropharmacology. 1994 Nov;33(11):1261-5. PubMed PMID: 7532812. 9: Yokoi I, Kabuto H, Habu H, Mori A. alpha-Guanidinoglutaric acid, an endogenous convulsant, as a novel nitric oxide synthase inhibitor. J Neurochem. 1994 Oct;63(4):1565-7. PubMed PMID: 7523594. 10: Mori A. Biochemistry and neurotoxicology of guanidino compounds. History and recent advances. Pavlov J Biol Sci. 1987 Jul-Sep;22(3):85-94. Review. PubMed PMID: 2821470. 11: Shiraga H, Hiramatsu M, Mori A. Convulsive activity of alpha-guanidinoglutaric acid and the possible involvement of 5-hydroxytryptamine in the alpha-guanidinoglutaric acid-induced seizure mechanism. J Neurochem. 1986 Dec;47(6):1832-6. PubMed PMID: 3772379. 12: Natelson S. The lactam of alpha-guanidinoglutaric acid (1-amidino-2-pyrrolidone-5-carboxylic acid). Anal Biochem. 1986 Jul;156(1):31-7. PubMed PMID: 2874749. 13: Seki S, Yuyama N, Hiramatsu M. Effect of guanidino compounds on hen egg development. Adv Exp Med Biol. 1982;153:465-70. PubMed PMID: 7164920. 14: Mori A, Watanabe Y, Shindo S, Akagi M, Hiramatsu M. alpha-Guanidinoglutaric acid and epilepsy. Adv Exp Med Biol. 1982;153:419-26. PubMed PMID: 6819765. 15: Mori A, Akagi M, Katayama Y, Watanabe Y. alpha-Guanidinoglutaric acid in cobalt-induced epileptogenic cerebral cortex of cats. J Neurochem. 1980 Sep;35(3):603-5. PubMed PMID: 7452277.