5-Methyl-1H-pyrazole-3-carboxylic acid
5-Methyl-1H-pyrazole-3-carboxylic acid Basic information
- Product Name:
- 5-Methyl-1H-pyrazole-3-carboxylic acid
- Synonyms:
-
- 5-METHYL-2H-PYRAZOLE-3-CARBOXYLIC ACID
- 5-METHYLPYRAZOLE-3-CARBOXYLIC ACID
- 5-Methyl-1H-pyrazole-3-carboxylic acid ,97%
- U-19425
- 3-Carboxy-5-methyl-1H-pyrazole
- 5-Methyl-1H-pyrazole-3-ca...
- IFLAB-BB F0917-7550
- IFLAB-BB F2120-0002
- CAS:
- 402-61-9
- MF:
- C5H6N2O2
- MW:
- 126.11
- EINECS:
- 673-162-9
- Product Categories:
-
- Building Blocks
- Heterocyclic Building Blocks
- Pyrazoles
- Pyrazole
- Heterocyclic Compounds
- Mol File:
- 402-61-9.mol
5-Methyl-1H-pyrazole-3-carboxylic acid Chemical Properties
- 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
- 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)
MSDS
- Language:English Provider:SigmaAldrich
5-Methyl-1H-pyrazole-3-carboxylic acid Usage And Synthesis
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
67-51-6
3112-31-0
402-61-9
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
5-Methyl-1H-pyrazole-3-carboxylic acid Preparation Products And Raw materials
Raw materials
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5-Methyl-1H-pyrazole-3-carboxylic acid(402-61-9)Related Product Information
- 5-METHYL-1H-PYRROLE-2-CARBOXYLIC ACID
- 1,5-DIMETHYL-1H-PYRAZOLE-3-CARBOXYLIC ACID
- 5-Methyl-1H-pyrazole-3-carboxylic acid
- 1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
- ETHYL 1,5-DIMETHYL-1H-PYRAZOLE-3-CARBOXYLATE
- Ethyl 3-methyl-1H-pyrazole-5-carboxylate
- 3,5-PYRAZOLEDICARBOXYLIC ACID MONOHYDRATE
- 1,3-Dimethylpyrazole-5-carboxylic acid
- 1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
- 1-(TERT-BUTYL)-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
- Ethyl 5-thien-2-yl-1H-pyrazole-3-carboxylate
- 3,5-PYRAZOLEDICARBOXYLIC ACID
- 4-BROMO-1-ETHYL-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID,4-BROMO-1-ETHYL-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
- 5-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-1-methyl-1h-pyrazole-4-carboxylic acid
- ETHYL 1-(TERT-BUTYL)-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOXYLATE
- ETHYL 5-(2-FURYL)-1-METHYL-1H-PYRAZOLE-3-CARBOXYLATE
- ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
- 3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID