Basic information
- CAS
7554-65-6- Standard SMILES
Cc1cn[nH]c1- InChIKey
RIKMMFOAQPJVMX-UHFFFAOYSA-N- Molecular formula
- C4H6N2
- Average molar mass
- 82.1 g/mol
- Monoisotopic mass
- 82.0530982
Names & identifiers
- Preferred name
- 4-Methylpyrazole
- IUPAC
- 4-methyl-1H-pyrazole
- English name
- 4-Methylpyrazole
- Molecular formula
- C4H6N2
- Molecular weight
- 82.1
Names & synonyms
Show more names
Database identifiers
- CAS
7554-65-6- PubChem CID
- 3406
- DTXSID
DTXSID3040649- ChEMBL
CHEMBL1308- ChEBI
CHEBI:5141- UNII
- 83LCM6L2BY
- EC Number
- 231-445-0
- Nikkaji
- J35.396E
Properties
Computed structural properties
- XLogP
- 1.4
- Topological polar surface area
- 28.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 6
- Formal charge
- 0
- Complexity
- 44
Physicochemical properties
- Melting point
- 13 °C · 13°C
- Boiling point
- 99 · 99-100 °C6 mm Hg(lit.)
- Density
- 0.993 g/mL · 0.993 g/mL at 25 °C(lit.)
- vapor pressure
- 7.136 · 7.136-87.85Pa at 20-50℃
- refractive index
- 20 · n20/D 1.495(lit.)
- Flash point
- 205 °F · 205 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble
- pka
- 14.95 · 14.95±0.50(Predicted)
- form
- Liquid After Melting
- color
- Clear colorless to yellow
- Specific Gravity
- 0.993 · 0.993
- Water Solubility
- soluble
- Sensitive
- Hygroscopic
- Merck
- 14 · 14,4226
- BRN
- 105204 · 105204
- InChI
- 1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
- InChIKey
- RIKMMFOAQPJVMX-UHFFFAOYSA-N
- SMILES
- Cc1cn[nH]c1
- LogP
- 1.097 · 1.097 (est)
- CAS DataBase Reference
- 7554 · 7554-65-6(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 83 LCM6L2BY · 83LCM6L2BY
- ATC code
- 3 AB34 · V03AB34
- NIST Chemistry Reference
- 4 · 4-methylpyrazole(7554-65-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36-24/25
- RIDADR
- 2810 · 2810
- WGK Germany
- 3 · 3
- RTECS
- 7350000 · UQ7350000
- F
- 10 · 10-23
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29331990 · 29331990
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 · LD50 (7 days) in mice, rats (mmol/kg): 3.8, 3.8 i.v.; 7.8, 6.5 orally (Magnusson)
- REACH Registrations
- Inactive
Safety & regulation
Safety data
- F
- 10-23
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- rtecs
- UQ7350000
- ridadr
- 2810
- hs_code
- 29331990
- Toxicity
- LD50 (7 days) in mice, rats (mmol/kg): 3.8, 3.8 i.v.; 7.8, 6.5 orally (Magnusson)
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36-24/25
- hazard_class
- 6.1(b)
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- REACH Registrations
- Inactive
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionFomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes metabolism of ethylene glycol and methanol to toxic metabolites. At 10 μM in monkeys, it can prevent the formation of toxic alcohol metabolites that generate metabolic acidosis. This compound is typically used as an antidote for ethylene glycol or methanol poisoning.
DescriptionFomepizole is the first drug indicated as an antidote for ethylene glycol poisoning (it has also shown promise as a treatment for methanol poisoning). Fomepizole is 4-methyl-1H-pyrazole active as a synthetic alcohol dehydrogenase inhibitor, blocking the formation of toxic ethylene glycol metabolites which are responsible for a severe metabolic acidosis and renal failure. In limited human studies, it reversed the toxicity of potentially lethal doses of ethylene glycol. The main urinary metabolite has been reported to be 4-carboxypyrazole by oxidation of the methyl group. Compared with the current treatment (ethanol), the duration of action is longer and the safety is improved, with no toxic effects reported.
UsesFomepizole (4-Methylpyrazole) can be used as: A reactant to prepare 4-methyl-1-phenyl-1H-pyrazole by reacting with bromobenzene via N-arylation using a copper catalyst. A starting material for the synthesis of 4-methyl-3(5)-nitropyrazole by nitration. A ligand in the preparation of gallium(III) complex of 4-methylpyrazole as potential antitumor and antiviral agent.
UsesUseful as an antidote in methanol and ethylene glycol poisoning.
UsesAntidote in methanol or ethylene glycol poisoning;Alcohol dehydrogenase inhibitor
Usesantidote to ethylene glycol or methanol poisoning
General Description4-Methylpyrazole inhibits CYP2E1 activity. It also acts as alcohol dehydrogenase inhibitor.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Additional notes
DefinitionChEBI: A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.
Related reactions
Compound notes
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