Global Information Lookup Global Information

Quisqualic acid information


Quisqualic acid
Names
IUPAC name
3-(3,5-Dioxo-1,2,4-oxadiazolidin-2-yl)-L-alanine
Systematic IUPAC name
(2S)-2-Amino-3-(3,5-dioxo-1,2,4-oxadiazolidin-2-yl)propanoic acid
Identifiers
CAS Number
  • 52809-07-1 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL279956 checkY
ChemSpider
  • 37038 checkY
DrugBank
  • DB02999 checkY
ECHA InfoCard 100.164.809 Edit this at Wikidata
EC Number
  • 637-070-2
IUPHAR/BPS
  • 1372
  • 1370
KEGG
  • C08296 checkY
MeSH Quisqualic+Acid
PubChem CID
  • 40539
UNII
  • 8OC22C1B99 checkY
CompTox Dashboard (EPA)
  • DTXSID20896927 Edit this at Wikidata
InChI
  • InChI=1S/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1 checkY
    Key: ASNFTDCKZKHJSW-REOHCLBHSA-N checkY
  • InChI=1/C5H7N3O5/c6-2(3(9)10)1-8-4(11)7-5(12)13-8/h2H,1,6H2,(H,9,10)(H,7,11,12)/t2-/m0/s1
    Key: ASNFTDCKZKHJSW-REOHCLBHBE
SMILES
  • O=C1NC(=O)ON1C[C@H](N)C(=O)O
Properties
Chemical formula
C5H7N3O5
Molar mass 189.126 g/mol
Melting point 187 to 188 °C (369 to 370 °F; 460 to 461 K) decomposes
Hazards
GHS labelling:[1]
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H302, H312, H332
Precautionary statements
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Quisqualic acid is an agonist of the AMPA, kainate, and group I metabotropic glutamate receptors. It is one of the most potent AMPA receptor agonists known.[2][3][4][5] It causes excitotoxicity and is used in neuroscience to selectively destroy neurons in the brain or spinal cord.[6][7][8] Quisqualic acid occurs naturally in the seeds of Quisqualis species.

Research conducted by the USDA Agricultural Research Service, has demonstrated quisqualic acid is also present within the flower petals of zonal geranium (Pelargonium x hortorum) and is responsible for causing rigid paralysis of the Japanese beetle.[9][10] Quisqualic acid is thought to mimic L-glutamic acid, which is a neurotransmitter in the insect neuromuscular junction and mammalian central nervous system.[11]

  1. ^ "Quisqualic acid". pubchem.ncbi.nlm.nih.gov.
  2. ^ Jin R, Horning M, Mayer ML, Gouaux E (December 2002). "Mechanism of activation and selectivity in a ligand-gated ion channel: structural and functional studies of GluR2 and quisqualate". Biochemistry. 41 (52): 15635–15643. doi:10.1021/bi020583k. PMID 12501192.
  3. ^ Kuang D, Hampson DR (June 2006). "Ion dependence of ligand binding to metabotropic glutamate receptors". Biochemical and Biophysical Research Communications. 345 (1): 1–6. doi:10.1016/j.bbrc.2006.04.064. PMID 16674916.
  4. ^ Zhang W, Robert A, Vogensen SB, Howe JR (August 2006). "The relationship between agonist potency and AMPA receptor kinetics". Biophysical Journal. 91 (4): 1336–1346. Bibcode:2006BpJ....91.1336Z. doi:10.1529/biophysj.106.084426. PMC 1518651. PMID 16731549.
  5. ^ Bigge CF, Boxer PA, Ortwine DF (August 1996). "AMPA/Kainate Receptors". Current Pharmaceutical Design. 2 (4): 397–412. doi:10.2174/1381612802666220925204342. S2CID 252560966.
  6. ^ Muir JL, Page KJ, Sirinathsinghji DJ, Robbins TW, Everitt BJ (November 1993). "Excitotoxic lesions of basal forebrain cholinergic neurons: effects on learning, memory and attention". Behavioural Brain Research. 57 (2): 123–131. doi:10.1016/0166-4328(93)90128-d. PMID 7509608. S2CID 3994174.
  7. ^ Giovannelli L, Casamenti F, Pepeu G (4 November 1998). "C-fos expression in the rat nucleus basalis upon excitotoxic lesion with quisqualic acid: a study in adult and aged animals". Journal of Neural Transmission. 105 (8–9): 935–948. doi:10.1007/s007020050103. PMID 9869327. S2CID 24942954.
  8. ^ Lee JW, Furmanski O, Castellanos DA, Daniels LA, Hama AT, Sagen J (July 2008). "Prolonged nociceptive responses to hind paw formalin injection in rats with a spinal cord injury". Neuroscience Letters. 439 (2): 212–215. doi:10.1016/j.neulet.2008.05.030. PMC 2680189. PMID 18524486.
  9. ^ Flores A (March 2010). "Geraniums and Begonias: New Research on Old Garden Favorites". Agricultural Research Magazine.
  10. ^ Ranger CM, Winter RE, Singh AP, Reding ME, Frantz JM, Locke JC, Krause CR (January 2011). "Rare excitatory amino acid from flowers of zonal geranium responsible for paralyzing the Japanese beetle". Proceedings of the National Academy of Sciences of the United States of America. 108 (4): 1217–1221. Bibcode:2011PNAS..108.1217R. doi:10.1073/pnas.1013497108. PMC 3029778. PMID 21205899.
  11. ^ Usherwood PN (1 January 1994). "Insect Glutamate Receptors". Advances in Insect Physiology. 24: 309–341. doi:10.1016/S0065-2806(08)60086-7. ISBN 9780120242245.

and 29 Related for: Quisqualic acid information

Request time (Page generated in 1.8468 seconds.)

Quisqualic acid

Last Update:

Quisqualic acid is an agonist of the AMPA, kainate, and group I metabotropic glutamate receptors. It is one of the most potent AMPA receptor agonists...

Word Count : 3541

Glutamic acid

Last Update:

Glutamic acid (symbol Glu or E; the anionic form is known as glutamate) is an α-amino acid that is used by almost all living beings in the biosynthesis...

Word Count : 3213

Muscimol

Last Update:

compounds responsible for the effects of Amanita muscaria intoxication. Ibotenic acid, a neurotoxic secondary metabolite of Amanita muscaria, serves as a prodrug...

Word Count : 2462

Alanine

Last Update:

α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the...

Word Count : 2180

Saffron

Last Update:

di-(β-D-gentiobiosyl) ester; it bears the systematic (IUPAC) name 8,8-diapo-8,8-carotenoic acid. This means that the crocin underlying saffron's aroma is a digentiobiose...

Word Count : 7852

Nitric oxide

Last Update:

to produce nitric acid (HNO3): •NO + HO• 2 → •NO2 + •OH •NO2 + •OH → HNO3 Nitric acid, along with sulfuric acid, contributes to acid rain deposition. •NO...

Word Count : 2754

Ibotenic acid

Last Update:

ibotenic acid, likely by enzymes encoded in the biosynthetic gene cluster. Conotoxin Grayanotoxin Quisqualic acid Tetrodotoxin "Ibotenic acid". pubchem...

Word Count : 1473

Domoic acid

Last Update:

Pseudo-nitzschia Quisqualic acid Brevetoxin Ciguatoxin Okadaic acid Saxitoxin Maitotoxin Clayden J, Read B, Hebditch KR (2005). "Chemistry of domoic acid, isodomoic...

Word Count : 1841

Fluorexetamine

Last Update:

(acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide...

Word Count : 166

Aspartic acid

Last Update:

aspartic acid is one of the 22 proteinogenic amino acids, i.e., the building blocks of proteins. D-aspartic acid is one of two D-amino acids commonly...

Word Count : 1867

Glycine

Last Update:

/ˈɡlaɪsiːn/ ) is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid (carbamic acid is unstable). In the...

Word Count : 3236

Combretum indicum

Last Update:

species, Quisqualis fructus and Q. chinensis, contain the chemical quisqualic acid, which is an agonist for the AMPA receptor, a kind of glutamate receptor...

Word Count : 687

Agmatine

Last Update:

Kossel. It is a chemical substance which is naturally created from the amino acid arginine. Agmatine has been shown to exert modulatory action at multiple...

Word Count : 1914

Hydrochlorothiazide

Last Update:

(high levels of uric acid in the blood). All thiazide diuretics including hydrochlorothiazide can inhibit excretion of uric acid by the kidneys, thereby...

Word Count : 2187

AMPA receptor

Last Update:

Glutamic acid (glutamate) – the endogenous agonist Ibotenic acid – a naturally occurring agonist found in Amanita muscaria Quisqualic acid – a naturally...

Word Count : 7019

Atomoxetine

Last Update:

is highly bound to plasma proteins (98.7%), mainly albumin, along with α1-acid glycoprotein (77%) and IgG (15%). Its metabolite N-desmethylatomoxetine is...

Word Count : 5911

Deoxymethoxetamine

Last Update:

(acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide...

Word Count : 142

Glutathione

Last Update:

catalyzes the hydrolysis of S-D-lactoylglutathione to glutathione and D-lactic acid. It maintains exogenous antioxidants such as vitamins C and E in their reduced...

Word Count : 2176

Chloroform

Last Update:

formyle, an obsolete name for the methylidene radical (CH) derived from formic acid. The total global flux of chloroform through the environment is approximately...

Word Count : 5618

Glutamine

Last Update:

an α-amino acid that is used in the biosynthesis of proteins. Its side chain is similar to that of glutamic acid, except the carboxylic acid group is replaced...

Word Count : 2443

Excitatory amino acid receptor agonist

Last Update:

Glutamic acid Ibotenic acid Kainic acid N-Methyl-D-aspartic acid Quisqualic acid Excitatory amino acid receptor antagonist Excitatory amino acid reuptake...

Word Count : 73

Methylene blue

Last Update:

Hyoscyamine/­hexamethylenetetramine/­phenyl salicylate/­methylene blue/­benzoic acid (trade names Methylphen, Prosed DS) is a discontinued drug combination. It...

Word Count : 5613

Spermine

Last Update:

all eukaryotic cells. The precursor for synthesis of spermine is the amino acid ornithine. It is an essential growth factor in some bacteria as well. It...

Word Count : 704

Putrescine

Last Update:

microalgae, together with spermine and spermidine. Putrescine reacts with adipic acid to yield the polyamide nylon 46, which is marketed by DSM under the trade...

Word Count : 1496

Apigenin

Last Update:

aromatic amino acids L-phenylalanine or L-tyrosine, both products of the Shikimate pathway. When starting from L-phenylalanine, first the amino acid is non-oxidatively...

Word Count : 967

Bumetanide

Last Update:

4-chlorobenzoic acid. In the first stage of synthesis, it undergoes sulfonylchlorination by chlorosulfonic acid, forming 4-chloro-3-chlorosulfonylbenzoic acid, which...

Word Count : 1371

Serine

Last Update:

Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated −NH+...

Word Count : 2403

Glutamate receptor

Last Update:

membranes of neuronal and glial cells. Glutamate (the conjugate base of glutamic acid) is abundant in the human body, but particularly in the nervous system and...

Word Count : 6876

Zinc

Last Update:

proteins, zinc ions are often coordinated to the amino acid side chains of aspartic acid, glutamic acid, cysteine and histidine. The theoretical and computational...

Word Count : 16879

PDF Search Engine © AllGlobal.net