4-Methylpyrazole

HCID 3406

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

4-Methylpyrazolefomepizole7554-65-61H-Pyrazole, 4-methyl-Fomepizol4-MethylpyrazolFomepizolum83LCM6L2BYNSC-760365CHEBI:5141DTXSID30406494 Methylpyrazole
Show more names
Antizol-VetAKOS B014452Antizol (TN)4-Fomepizole4-methyl-pyrazol
4 Methylpyrazole MonohydrochlorideRefChem:58530DTXCID1020649V03AB34231-445-04-Methyl-1H-pyrazoleAntizolFomepizol [INN-Spanish]

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

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

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

Chemistry & industry

Applications · 7 items

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.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Additional notes

DefinitionChEBI: A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.

Related reactions

110 records

Compound notes

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