Xanthurenic acid

Names

[ CAS No. ]:
59-00-7

[ Name ]:
Xanthurenic acid

[Synonym ]:
4,8-Dihydroxy-2-quinolinecarboxylic acid
EINECS 200-410-1
4,8-dihydroxy-Quinaldic acid
4,8-Dihydroxyquinoline-2-carboxylic acid
2-quinolinecarboxylic acid, 1,4-dihydro-8-hydroxy-4-oxo-
8-hydroxy-4-oxo-1H-quinoline-2-carboxylic acid
Xanthurenate
Xanthurenic acid
MFCD00006754
2-Quinolinecarboxylic acid, 4,8-dihydroxy-

Biological Activity

[Description]:

Xanthurenic acid is a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> mGluR

Research Areas >> Metabolic Disease

Natural Products >> Acids and Aldehydes

Research Areas >> Neurological Disease

[Target]

Human Endogenous Metabolite

mGluR2

mGluR3

[In Vivo]

Xanthurenic acid is a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus. The inhibition of Xanthurenic acid (XA) on sensory can be found when applied iontophoretically and i.v., is similar to that of other Group II mGlu receptor agonists in reducing inhibition evoked in the VB from the thalamic reticular nucleus upon physiological sensory stimulation. Furthermore, it is postulated that Xanthurenic acid may be the first potential endogenous allosteric agonist for the mGlu receptors. As the Group II receptors and kynurenine metabolism pathway have both been heavily implicated in the pathophysiology of schizophrenia, Xanthurenic acid could play a pivotal role in antipsychotic research as this potential endocoid represents both a convergence within these two biological parameters and a novel class of Group II mGlu receptor ligand[1].

[Animal admin]

Rats[1]Male Wistar rats (265-495 g, n=27) are used throughout the study. Throughout the experiments, electrocardiogram and electroencephalogram (EEG) are monitored. Iontophoretic drug applications are performed using the outer barrels, with one of the outer barrels filled with 1 M NaCl for current balancing on each occasion. The remaining outer barrels contain one of the following substances as required: NMDA (50 mM,pH8.0 in 150 mM NaCl), LY354740 (5 mM, pH8.0 in 75 mM NaCl), Xanthurenic Acid (5 mM, pH8.0 in 75 mM NaCl), LY341495 (5 mM, pH8.5 in 75mM NaCl), as Nat salts, ejected as anions, and LY487379 (1 mM, pH6.0, in 1% dimethyl sulfoxide, 75mM NaCl), ejected as cations. All compounds are prevented from diffusing out of the pipette by using a retaining current (15-25 nA) of opposite polarity to that of the ejection current[1].

[References]

[1]. Copeland CS, et al. Actions of Xanthurenic acid, a putative endogenous Group II metabotropic glutamate receptor agonist, on sensory transmission in the thalamus. Neuropharmacology. 2013 Mar;66:133-42.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
514.4±50.0 °C at 760 mmHg

[ Melting Point ]:
297-298 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₀H₇NO₄

[ Molecular Weight ]:
205.167

[ Flash Point ]:
264.9±30.1 °C

[ Exact Mass ]:
205.037506

[ PSA ]:
90.65000

[ LogP ]:
2.64

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.779

[ Storage condition ]:
Store at RT

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UZ9275000

CHEMICAL NAME :: Quinaldic acid, 4,8-dihydroxy-

CAS REGISTRY NUMBER :: 59-00-7

BEILSTEIN REFERENCE NO. :: 0185954

LAST UPDATED :: 199709

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H7-N-O4

MOLECULAR WEIGHT :: 205.18

WISWESSER LINE NOTATION :: T66 BNJ CVQ EQ JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 160 mg/kg

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - tumors

REFERENCE :: ANYAA9 Annals of the New York Academy of Sciences. (New York Academy of Sciences, 2 E. 63rd St., New York, NY 10021) V.1- 1877- Volume(issue)/page/year: 108,924,1963 *** REVIEWS *** TOXICOLOGY REVIEW AEHLAU Archives of Environmental Health. (Heldref Pub., 4000 Albemarle St., NW, Washington, DC 20016) V.1- 1960- Volume(issue)/page/year: 23,6,1971

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
UZ9275000

Articles

Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.

J. Chromatogr. A. 562(1-2) , 125-38, (1991)

Eighty-five clinical urine samples and nineteen urine samples previously found by other laboratories to suggest genetic metabolic defects were prepared for trimethylsilylation by treatment with urease...

Vitamin B1 deficiency inhibits the increased conversion of tryptophan to nicotinamide in severe food-restricted rats.

Biosci. Biotechnol. Biochem. 79(1) , 103-8, (2015)

The conversion of tryptophan (Trp) → nicotinamide (Nam) is an important pathway for supplying vitamin niacin. We reported the following two phenomena: (1) severe food restriction led to an increase in...

The urinary ratio of 3-hydroxykynurenine/3-hydroxyanthranilic acid is an index to predicting the adverse effects of D-tryptophan in rats.

J. Nutr. Sci. Vitaminol. 60(4) , 261-8, (2014)

The adverse effects of D-tryptophan and the possibility of it being a surrogate index for predicting adverse effects in rats were investigated. Male rats were fed one of several test diets (20% casein...

Related Compounds

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