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222569

Sigma-Aldrich

Fomepizole

99%

Synonym(s):

4-Methylpyrazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
Molecular Weight:
82.10
Beilstein:
105204
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.495 (lit.)

bp

99-100 °C/6 mmHg (lit.)

solubility

alcohol: soluble(lit.)
water: soluble(lit.)

density

0.993 g/mL at 25 °C (lit.)

SMILES string

Cc1cn[nH]c1

InChI

1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)

InChI key

RIKMMFOAQPJVMX-UHFFFAOYSA-N

Gene Information

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General description

4-Methylpyrazole inhibits CYP2E1 activity. It also acts as alcohol dehydrogenase inhibitor.

Application

Fomepizole (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.

Useful as an antidote in methanol and ethylene glycol poisoning.

Biochem/physiol Actions

Alcohol dehydrogenase inhibitor
Alcohol dehydrogenase inhibitor.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Samjhana Thapaliya et al.
Autophagy, 10(4), 677-690 (2014-02-05)
Patients with alcoholic cirrhosis and hepatitis have severe muscle loss. Since ethanol impairs skeletal muscle protein synthesis but does not increase ubiquitin proteasome-mediated proteolysis, we investigated whether alcohol-induced autophagy contributes to muscle loss. Autophagy induction was studied in: A) Human
J Samuelson et al.
Archives of medical research, 23(2), 31-33 (1992-01-01)
Ethanol is the major metabolic product of glucose fermentation by the protozoan parasite E. histolytica under the anaerobic conditions found in the lumen of the colon. With the goal of finding new targets for anti-amebic drugs, the E. histolytica NADP(+)-dependent
Nitropyrazoles 17. Synthesis of 1-(3, 5-dinitrophenyl)-4-methyl-3, 5-dinitropyrazole and the study of its chemical transformations
Zaitsev AA, et al.
Russian Chemical Bulletin, 58(10), 2122-2128 (2009)
Mild Conditions for Copper-Catalysed N-Arylation of Pyrazoles
Cristau H-J, et al.
European Journal of Organic Chemistry, 2004(4), 695-709 (2004)
Synthesis and characterization of potential antitumour and antiviral gallium (III) complexes of N-heterocycles
Kratz F, et al.
Polyhedron, 11(4), 487-498 (1992)

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