Antipyrine

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  • Identifiers

    CAS number
    60-80-0

    Molecular formula
    C11H12N2O

    SMILES
    CC1=CC(=O)N(N1C)C2=CC=CC=C2

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 35.61%
    Burnt 33.17%
    Roasted 30.24%
    Bitter 29.27%
    Fruity 29.16%
    Animal 27.43%
    Musty 25.9%
    Grape 25.6%
    Cooked 21.98%
    Nutty 21.57%

     

    Flavor
    Bitter 78.94%
    Odorless 25.35%
    Very strong 22.35%
    Indole 21.94%
    Nitrile 21.75%
    Bread crust 21.33%
    Soybean 20.66%
    Roasted peanuts 20.51%
    Cedarleaf 20.5%
    Orange flower 20.37%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.4

    pKa est.
    4.92 (weak acid)

    Molecular weight
    188.23 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 114 °C
    • 113 °C

    Boiling point

    • 319 °C

    Flash point

    • 127.57 ˚C est.

    Solubility expt.

    • 51900 mg/L (at 25 °C)
    • 4.74e+01 g/L
    • Solubility in water: very good
    • 25.2 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • antipyrine
    • Phenazone
    • 60-80-0
    • Analgesine
    • Antipyrin
    • Fenazone
    • Antipyrinum
    • 2,3-Dimethyl-1-phenyl-5-pyrazolone
    • Phenazonum
    • Fenazona
    • 3H-Pyrazol-3-one, 1,2-dihydro-1,5-dimethyl-2-phenyl-
    • 2,3-Dimethyl-1-phenyl-3-pyrazolin-5-one
    • 1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
    • 1,5-Dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
    • 1,5-dimethyl-2-phenylpyrazol-3-one
    • DTXSID6021117
    • CHEBI:31225
    • 1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
    • T3CHA1B51H
    • DTXCID401117
    • RefChem:54230
    • N02BB01
    • S02DA03
    • 200-486-6
    • Anodynin
    • Anodynine
    • Azophen
    • Antipirin
    • Phenozone
    • Phenylone
    • Dimethyloxychinizin
    • Apirelina
    • Azophene
    • Methozin
    • Parodyne
    • Pyrazophyl
    • Sedatine
    • Dimethyloxyquinazine
    • Oxydimethylquinazine
    • Azophenum
    • Phenylon
    • 3-Antipyrine
    • Fenazon [Czech]
    • Oxydimethylquinizine
    • Fenazona [INN-Spanish]
    • Phenazone (pharmaceutical)
    • Fenazon
    • 1-Phenyl-2,3-dimethyl-5-pyrazolone
    • MFCD00003146
    • 1-Phenyl-2,3-dimethylpyrazole-5-one
    • NSC 7945
    • Phenazone;Phenazon
    • Phenazone [INN]
    • 1,5-dimethyl-2-phenyl-pyrazol-3-one
    • Phenazone (INN)
    • NSC-7945
    • s3173
    • CAS-60-80-0
    • NCGC00016274-04
    • Antipyrine [JAN]
    • 2-Trideuteromethyl-3-methyl-1-phenyl-3-pyrazolin-5-one
    • Phenazonum [INN-Latin]
    • SMR000238140
    • CCRIS 1369
    • Antipyrine [USP:JAN]
    • SR-05000001566
    • EINECS 200-486-6
    • pyrazole, 2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-
    • UNII-T3CHA1B51H
    • Antipyrien
    • AI3-15293
    • Phenazone CRS
    • .beta.-Antipyrine
    • Prestwick_26
    • component of Auralgan
    • Antipyrine (Standard)
    • Spectrum_000058
    • ANTIPYRINE [MI]
    • Prestwick0_000029
    • Prestwick1_000029
    • Prestwick2_000029
    • Prestwick3_000029
    • Spectrum2_000088
    • Spectrum3_000305
    • Spectrum4_000152
    • Spectrum5_000842
    • ANTIPYRINE [VANDF]
    • ANTIPYRINUM [HPUS]
    • Antipyrine (JP17/USP)
    • Epitope ID:124927
    • PHENAZONE [MART.]
    • EC 200-486-6
    • PHENAZONE [WHO-DD]
    • 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
    • ANTIPYRINE [USP-RS]
    • Auralgan component antipyrine
    • 1,5-dimethyl-2-phenyl-1,2-dihydropyrazol-3-one
    • SCHEMBL20452
    • BSPBio_000097
    • BSPBio_001870
    • KBioGR_000624
    • KBioSS_000438
    • MLS001331753
    • MLS001332401
    • MLS001332402
    • MLS002154179
    • DivK1c_000484
    • SPECTRUM1500128
    • SPBio_000016
    • SPBio_002018
    • Antipyrine, analytical standard
    • BPBio1_000107
    • CHEMBL277474
    • orb1310338
    • SCHEMBL3065572
    • PHENAZONE [EP IMPURITY]
    • PHENAZONE [EP MONOGRAPH]
    • HMS501I06
    • HY-B0171R
    • KBio1_000484
    • KBio2_000438
    • KBio2_003006
    • KBio2_005574
    • KBio3_001370
    • ANTIPYRINE [USP IMPURITY]
    • MSK7125
    • NSC7945
    • 60-80-0

  • Applications

    Antipyrine is primarily used in medicine as an analgesic and antipyretic in historical or regional formulations; beyond its therapeutic use, it is employed as a probe drug in pharmacokinetic research to evaluate hepatic metabolic capacity and renal excretion, and as a marker for studying drug disposition in laboratory settings. In analytical contexts, antipyrine serves as a reference compound for method development and validation, aiding quantification in biological matrices by HPLC or LC-MS and supporting quality control of assays. In vitro pharmacology, it is used to investigate drug metabolism and cytochrome P450 enzyme activity and potential interactions. In pharmaceutical development and analytics, antipyrine is often treated as a standard tool for metabolic and clearance studies, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 553.27
    methanol 888.26
    isopropanol 339.82
    water 555.53
    ethyl acetate 116.48
    n-propanol 452.29
    acetone 292.74
    n-butanol 334.74
    acetonitrile 416.87
    DMF 717.24
    toluene 117.94
    isobutanol 349.75
    1,4-dioxane 428.95
    methyl acetate 175.69
    THF 402.93
    2-butanone 215.51
    n-pentanol 221.8
    sec-butanol 300.07
    n-hexane 9.78
    ethylene glycol 340.59
    NMP 384.22
    cyclohexane 29.9
    DMSO 461.4
    n-butyl acetate 71.41
    n-octanol 77.54
    chloroform 1194.47
    n-propyl acetate 80.85
    acetic acid 328.76
    dichloromethane 1173.59
    cyclohexanone 343.03
    propylene glycol 268.41
    isopropyl acetate 67.55
    DMAc 432.98
    2-ethoxyethanol 280.79
    isopentanol 207.06
    n-heptane 8.46
    ethyl formate 252.08
    1,2-dichloroethane 518.53
    n-hexanol 136.8
    2-methoxyethanol 621.21
    isobutyl acetate 55.43
    tetrachloromethane 130.81
    n-pentyl acetate 63.08
    transcutol 265.6
    n-heptanol 72.05
    ethylbenzene 73.23
    MIBK 88.88
    2-propoxyethanol 196.4
    tert-butanol 240.25
    MTBE 103.51
    2-butoxyethanol 120.0
    propionic acid 233.91
    o-xylene 85.12
    formic acid 372.11
    diethyl ether 124.7
    m-xylene 77.12
    p-xylene 108.43
    chlorobenzene 229.66
    dimethyl carbonate 109.16
    n-octane 6.45
    formamide 622.04
    cyclopentanone 352.8
    2-pentanone 141.09
    anisole 144.9
    cyclopentyl methyl ether 140.85
    gamma-butyrolactone 386.43
    1-methoxy-2-propanol 311.08
    pyridine 404.9
    3-pentanone 124.7
    furfural 451.37
    n-dodecane 7.54
    diethylene glycol 250.23
    diisopropyl ether 30.54
    tert-amyl alcohol 189.01
    acetylacetone 147.96
    n-hexadecane 8.54
    acetophenone 139.39
    methyl propionate 138.9
    isopentyl acetate 72.75
    trichloroethylene 879.48
    n-nonanol 64.94
    cyclohexanol 236.36
    benzyl alcohol 186.09
    2-ethylhexanol 64.63
    isooctanol 56.25
    dipropyl ether 49.29
    1,2-dichlorobenzene 197.64
    ethyl lactate 81.42
    propylene carbonate 236.14
    n-methylformamide 497.9
    2-pentanol 158.6
    n-pentane 12.78
    1-propoxy-2-propanol 106.23
    1-methoxy-2-propyl acetate 87.64
    2-(2-methoxypropoxy) propanol 96.2
    mesitylene 44.59
    ε-caprolactone 225.6
    p-cymene 38.74
    epichlorohydrin 474.98
    1,1,1-trichloroethane 343.5
    2-aminoethanol 477.99
    morpholine-4-carbaldehyde 351.95
    sulfolane 386.22
    2,2,4-trimethylpentane 9.27
    2-methyltetrahydrofuran 240.32
    n-hexyl acetate 93.03
    isooctane 5.63
    2-(2-butoxyethoxy)ethanol 137.56
    sec-butyl acetate 52.23
    tert-butyl acetate 70.16
    decalin 14.58
    glycerin 341.46
    diglyme 235.31
    acrylic acid 260.98
    isopropyl myristate 41.79
    n-butyric acid 248.94
    acetyl acetate 95.88
    di(2-ethylhexyl) phthalate 57.67
    ethyl propionate 85.94
    nitromethane 441.94
    1,2-diethoxyethane 88.47
    benzonitrile 211.08
    trioctyl phosphate 38.96
    1-bromopropane 227.19
    gamma-valerolactone 423.14
    n-decanol 51.39
    triethyl phosphate 50.33
    4-methyl-2-pentanol 74.07
    propionitrile 288.92
    vinylene carbonate 278.58
    1,1,2-trichlorotrifluoroethane 327.24
    DMS 105.89
    cumene 49.92
    2-octanol 52.78
    2-hexanone 96.63
    octyl acetate 55.71
    limonene 48.2
    1,2-dimethoxyethane 349.13
    ethyl orthosilicate 45.83
    tributyl phosphate 45.5
    diacetone alcohol 114.43
    N,N-dimethylaniline 97.19
    acrylonitrile 397.14
    aniline 196.87
    1,3-propanediol 468.25
    bromobenzene 215.1
    dibromomethane 683.21
    1,1,2,2-tetrachloroethane 605.04
    2-methyl-cyclohexyl acetate 70.28
    tetrabutyl urea 64.8
    diisobutyl methanol 37.18
    2-phenylethanol 123.08
    styrene 93.86
    dioctyl adipate 62.62
    dimethyl sulfate 167.37
    ethyl butyrate 68.01
    methyl lactate 124.62
    butyl lactate 67.76
    diethyl carbonate 64.62
    propanediol butyl ether 116.15
    triethyl orthoformate 52.77
    p-tert-butyltoluene 33.9
    methyl 4-tert-butylbenzoate 99.45
    morpholine 404.49
    tert-butylamine 149.13
    n-dodecanol 41.17
    dimethoxymethane 312.77
    ethylene carbonate 219.92
    cyrene 133.79
    2-ethoxyethyl acetate 86.66
    2-ethylhexyl acetate 57.27
    1,2,4-trichlorobenzene 211.91
    4-methylpyridine 322.26
    dibutyl ether 54.35
    2,6-dimethyl-4-heptanol 37.18
    DEF 179.25
    dimethyl isosorbide 152.31
    tetrachloroethylene 427.12
    eugenol 118.35
    triacetin 90.63
    span 80 86.9
    1,4-butanediol 226.5
    1,1-dichloroethane 450.62
    2-methyl-1-pentanol 161.95
    methyl formate 384.7
    2-methyl-1-butanol 248.65
    n-decane 10.91
    butyronitrile 268.11
    3,7-dimethyl-1-octanol 60.51
    1-chlorooctane 45.81
    1-chlorotetradecane 21.57
    n-nonane 9.86
    undecane 8.9
    tert-butylcyclohexane 11.43
    cyclooctane 7.12
    cyclopentanol 286.48
    tetrahydropyran 283.58
    tert-amyl methyl ether 80.13
    2,5,8-trioxanonane 168.24
    1-hexene 49.21
    2-isopropoxyethanol 149.58
    2,2,2-trifluoroethanol 210.2
    methyl butyrate 128.96

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
 No restriction Category 7A
Rinse-off products applied to the hair with some hand contact
 No restriction
Category 2
Products applied to the axillae
 No restriction Category 7B
Leave-on products applied to the hair with some hand contact
 No restriction
Category 3
Products applied to the face/body using fingertips
 No restriction Category 8
Products with significant anogenital exposure
 No restriction
Category 4
Products related to fine fragrance
 No restriction Category 9
Products with body and hand exposure, primarily rinse off
 No restriction
Category 5A
Body lotion products applied to the body using the hands (palms), primarily leave on
 No restriction Category 10A
Household care products with mostly hand contact
 No restriction
Category 5B
Face moisturizer products applied to the face using the hands (palms), primarily leave on
 No restriction Category 10B
Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
Hand cream products applied to the hands using the hands (palms), primarily leave on
 No restriction Category 11A
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
 No restriction
Category 5D
Baby Creams, baby Oils and baby talc
 No restriction Category 11B
Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
 No restriction
Category 6
Products with oral and lip exposure
 No restriction Category 12
Products not intended for direct skin contact, minimal or insignificant transfer to skin
 No restriction