| Identification | More | [Name]
5-Methyl-1H-pyrazole-3-carboxylic acid | [CAS]
402-61-9 | [Synonyms]
3-METHYLPYRAZOLE-5-CARBOXYLIC ACID
5-METHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID
5-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID
5-METHYLPYRAZOLE-3-CARBOXYLIC ACID
AKOS B000144
AKOS BBS-00002591
AKOS PAO-0003
BUTTPARK 43\57-89
BUTTPARK 52\11-25
IFLAB-BB F0917-7550
IFLAB-BB F2120-0002
5-methyl-pyrazole-3-carboxylicaci
5-Methyl-1H-pyrazole-3-carboxylic acid ,97%
U-19425 | [EINECS(EC#)]
673-162-9 | [Molecular Formula]
C5H6N2O2 | [MDL Number]
MFCD00462235 | [Molecular Weight]
126.11 | [MOL File]
402-61-9.mol |
| Chemical Properties | Back Directory | [Melting point ]
241 °C | [Boiling point ]
388.8±22.0 °C(Predicted) | [density ]
1.404±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Soluble in dimethyl sulfoxide. | [form ]
powder to crystal | [pka]
15.36±0.10(Predicted) | [color ]
White to Yellow to Orange | [Detection Methods]
HPLC | [InChI]
InChI=1S/C5H6N2O2/c1-3-2-4(5(8)9)7-6-3/h2H,1H3,(H,6,7)(H,8,9) | [InChIKey]
WSMQKESQZFQMFW-UHFFFAOYSA-N | [SMILES]
N1C(C)=CC(C(O)=O)=N1 | [CAS DataBase Reference]
402-61-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-37/39 | [WGK Germany ]
3
| [RTECS ]
UQ6407500
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29331990 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
White to light yellow solid | [Uses]
3-Methylpyrazole-5-carboxylic acid is a potent and selective D-amino acid oxidase (DAO) (also known as DAAO, DAMOX and OXDA) inhibitor that protects DAO cells from oxidative stress induced by D-Serine. 3-Methylpyrazole-5-carboxylic acid specifically prevents formalin-induced tonic pain. | [Definition]
ChEBI: A memebr of the class of pyrazoles that is 1H-pyrazole with methyl and carboxylic acid group substituents at positions 5 and 3 respectively. | [General Description]
3-Methylpyrazole-5-carboxylic acid is a potent and selective D-amino acid oxidase (DAO) (also known as DAAO, DAMOX and OXDA) inhibitor that protects DAO cells from oxidative stress induced by D-Serine. 3-Methylpyrazole-5-carboxylic acid specifically prevents formalin-induced tonic pain. | [Synthesis]
General procedure for the synthesis of 3,5-pyrazoledicarboxylic acid and 5-methyl-1H-pyrazole-3-carboxylic acid from 3,5-dimethylpyrazole: 3,5-dimethyl-1H-pyrazole (78.5 g, 0.818 mol) was dissolved in 700 mL of water heated to 70 °C, potassium permanganate (517 g, 3.271 mol) was added slowly, and the temperature was kept no higher than 90 °C. After completion of the reaction, the mixture was cooled to room temperature, filtered to remove the resulting MnO2 precipitate, and washed with distilled water. The filtrate was acidified to pH 2 with dilute aqueous hydrochloric acid and allowed to stand overnight. The precipitate was collected by filtration and washed with distilled water to afford 3,5-pyrazoledicarboxylic acid (41.75 g, 33% yield) as white crystals with melting point 257-258 °C. 1H NMR (D2O, δ): 7.07 (s, 1H, 4-H). After isolation of 3,5-pyrazoledicarboxylic acid, the remaining aqueous phase filtrate was neutralized to pH 5-6, the precipitate was collected by filtration and washed with distilled water to afford 5-methyl-1H-pyrazole-3-carboxylic acid (18.1 g, 18% yield) as white crystals, melting point 210-211°C.1H NMR (D2O, δ): 2.25 (s, 3H, CH3), 6.42 (s, 1H, 4-H). 4-H). | [in vivo]
AS057278 (PO; 20 mg/kg b.i.d for 28 days; 80 mg/kg single dosage) normalizes?phencyclidine?(PCP)-induced?prepulse inhibition[1].
AS057278 (10 mg/kg; PO and IV; single dosage) exhibits good pharmacokinetic effects[1].
Pharmacokinetic Parameters of AS057278 in male Sprague-Dawley rats[1].
| IV (10 mg/kg) | PO (10 mg/kg) | | C0 (ng/mL) | 100,557.3 | | | Cmax (ng/mL) | 73,559.8 | 8088.8 | | tmax (h) | 0.083 | 1 | | CZ (ng/mL) | 26.8 | 40.5 | | tZ (h) | 24 | 24 | | AUCZ (ng/mL·h) | 45,596.2 | 18,254.4 | | λZ (h^-1) | 0.124 | 0.096 | | AUC (ng/mL·h) | 45,810.9 | 18,649.9 | | VZ (L/kg) | 1.76 | | | VSS (L/kg) | 0.24 | | | CL (L/kg/h) | 0.22 | | | MRT (h) | 1.087 | | | F | | 0.407 |
| Animal Model: | Males C57BL/6J mice[1] | | Dosage: | 80 mg/kg, 20 mg/kg | | Administration: | PO; 20 mg/kg b.i.d for 28 days; 80 mg/kg single dosage | | Result: | Normalized?phencyclidine?(PCP)-induced?prepulse inhibition?after acute (80?mg/kg) and chronic (20?mg/kg b.i.d.)?oral administration?in mice. |
| Animal Model: | Male Sprague-Dawley rats[1] | | Dosage: | 10 mg/kg | | Administration: | PO and IV; single dosage (Pharmacokinetics Analysis) | | Result: | Exhibited good pharmacokinetic effect. |
| [References]
[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 9, p. 1322 - 1325
[2] Zh. Org. Khim., 2016, vol. 52, # 9, p. 1334 - 1337,4 |
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