Antipyrine

HCID 2206CAS 60-80-0
Substructure searchFind similar structures

Basic information

Standard SMILES
Cc1cc(=O)n(-c2ccccc2)n1C
InChIKey
VEQOALNAAJBPNY-UHFFFAOYSA-N
Molecular formula
C11H12N2O
Average molar mass
188.23 g/mol
Monoisotopic mass
188.094963

Overview

Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, a xenobiotic, a cyclooxygenase 3 inhibitor and an environmental contaminant.

Names & identifiers

Preferred name
Antipyrine
IUPAC
1,5-dimethyl-2-phenylpyrazol-3-one
English name
Antipyrine
Molecular formula
C11H12N2O
Molecular weight
188.23

Names & synonyms

antipyrinePhenazone60-80-0AnalgesineAntipyrinFenazoneAntipyrinumPhenazonum2,3-Dimethyl-1-phenyl-5-pyrazoloneFenazona3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
Show more names
AntipirinANTIPYRENEPhenozoneAntypirine
1,5-dimethyl-2-phenylpyrazol-3-one1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-oneDTXSID6021117CHEBI:312251,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-oneT3CHA1B51HDTXCID401117

Database identifiers

CAS
60-80-0
PubChem CID
2206
DTXSID
DTXSID6021117
ChEMBL
CHEMBL277474
ChEBI
CHEBI:31225
UNII
T3CHA1B51H
EC Number
200-486-6
Nikkaji
J2.340J

Properties

Computed structural properties

XLogP
0.4
Topological polar surface area
23.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
14

Experimental & physicochemical properties

Chemical ClassesPharmaceutical
Drugs · 4 items

DEA NFLIS-Drug Category -> Analgesics

Pharmaceuticals -> Listed in ZINC15

Drug

Pharmaceuticals -> Metabolite of Metamizole

SpringerMaterials PropertiesCrystal structure
LogP · 3 items

0.38

0,23

0.42

DensityRelative density (water = 1): 1.19
Solubility · 3 items

4.74e+01 g/L

Solubility in water: very good

25.2 [ug/mL] (The mean of the results at pH 7.4)

Physicochemical properties

Melting point
109 · 109-111 °C(lit.)
Boiling point
319 °C · 319 °C
Density
1 · 1,19 g/cm3
refractive index
1.585 · 1.5850 (estimate)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: soluble1 gm in less than 1ml

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 0.5% (1 of 184) of reports.

Warning

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 184 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

REACH registered substance: Phenazone (EC: 200-486-6)

3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: Environment tier I assessment
Fire HazardsCombustible. Gives off irritating or toxic fumes (or gases) in a fire.
Chemical DangersDecomposes on heating. This produces toxic and corrosive fumes of nitrogen oxides. Reacts with strong oxidants.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
Hazard Classes and CategoriesAcute Tox. 4 (99.5%)

Safety & protection

Fire FightingUse water spray, powder, foam, carbon dioxide.
First Aid Measures · 4 items

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Seek medical attention if you feel unwell.

Safe StorageSeparated from strong oxidants.
Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.

Toxicology

Exposure RoutesThe substance can be absorbed into the body by inhalation of dust and by ingestion.
Signs and Symptoms · 4 items

Cough.

No acute symptoms expected.

Redness.

No acute symptoms expected.

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
USGS Health-Based Screening Levels for Evaluating Water-Quality · 3 items

Antipyrine

Pharmaceutical

Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP

Safety data

F
10
wgk
1
tsca
TSCA listed
rtecs
CD2450000
ridadr
3249
hs_code
29331190

Chemistry & industry

Pharmacology

ATC Code · 4 items

N - Nervous system

S - Sensory organs

QS - Sensory organs

QN - Nervous system

Pharmacodynamics · 1 item

Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

Mechanism of ActionAntipyrine is thought to act primarily in the CNS, increasing the pain threshold by inhibiting both isoforms of cyclooxygenase, COX-1, COX-2, and COX-3 enzymes involved in prostaglandin (PG) synthesis.
Metabolism/MetabolitesAntipyrine has known human metabolites that include Norantipyrine, 3-hydroxy-methylantipyrine, and 4-hydroxy-antipyrine.
MeSH Pharmacological Classification · 1 item

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Cellular LocationsCytoplasm

Uses & manufacturing

UsesUse (kg) in Switzerland (2009): >25
Use ClassificationPharmaceuticals
General Manufacturing Information3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-: ACTIVE
Applications · 3 items

HistoryAntipyrine (phenazone) was one of the first important synthetic Analgesic drugs that synthesis in Germany in 1884 by a pupil of Emil Fischer.

UsesAntipyrine has been used for immunoblotting. It has also been used as an internal reference marker for studying the transport characteristics of platinum-containing drug, cisplatin in the human placenta in vitro. Antipyrine is an analgesic and antipyretic that has been given by mouth and as ear drops. It is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29)

General DescriptionAntipyrine is an antipyretic agent used for the symptomatic treatment of acute otitis media, most commonly in combination with benzocaine. One of the earliest widely used analgesics and antipyretics, antipyrine was gradually replaced in common use by other medications including phenacetin (itself later withdrawn because of safety concerns), aspirin, paracetamol and modern NSAIDs such as ibuprofen.

Preparation methods · 1 item

PreparationAntipyrine (1) was prepared from the reaction of 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one with methyl iodide in methanol or in acetonitrile containing sodium bicarbonate in water in 58% yield. The reaction of 1-methyl-2-phenylhydrazine (2) with methyl 3-oxobutanoate (3) in acetonitrile gave 1 and pyrazolone 4 . Krohn has been reported the synthesis of 1 from the reaction of 5 with dimethyl sulfate in 71% yield. The reaction of pyrazolone 6 with methanol in the presence of triphenylphosphine afforded 1 (14%) and pyrazole 7 (53%). The same reaction was reported by Pegurier et al by heating the reactants in methanol containing calcium monoxide. Knorr early reported also, the synthesis of antipyrine from heating of 1-phenyl-5-ethoxy-3- methylpyrazole (8) with methyl iodide in methanol.

Upstream & downstream products

Suppliers50 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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Antipyrine is a pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at N-1 and C-5 and with a phenyl group at N-2. It has a role as a non-narcotic analgesic, an antipyretic, a non-steroidal anti-inflammatory drug, a cyclooxygenase 3 inhibitor, a xenobiotic and an environmental contaminant.

Related reactions

2 records
New reaction record

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