Aminopyrine

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  • Identifiers

    CAS number
    58-15-1

    Molecular formula
    C13H17N3O

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

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 34.64%
    Burnt 28.33%
    Fruity 27.76%
    Animal 25.83%
    Bitter 25.35%
    Grape 25.24%
    Roasted 23.62%
    Sweet 22.52%
    Dry 22.41%
    Musty 22.31%

     

    Flavor
    Bitter 69.07%
    Odorless 25.46%
    Roasted 20.73%
    Green pepper 20.58%
    Cedarleaf 20.46%
    Soybean 20.45%
    Very strong 20.24%
    Carrot 20.22%
    Syrup 20.07%
    Bread crust 20.06%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    1.0

    pKa est.
    4.51 (weak acid)

    Molecular weight
    231.29 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    586°C

    Melting point expt.

    • 225 to 228 °F (NTP, 1992)
    • 134.5 °C
    • 107-109 °C

    Flash point

    • 150.75 ˚C est.

    Solubility expt.

    • greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
    • 54400 mg/L (at 30 °C)
    • IN PRESENCE OF WATER, READILY ATTACKED BY MILD OXIDIZING AGENTS; ADDITION OF SODIUM BENZOATE TO WATER INCR SOLUBILITY
    • 1 G SOL IN 1.5 ML ALC, 12 ML BENZENE, 1 ML CHLOROFORM, 13 ML ETHER, 18 ML WATER
    • SOL IN PETROLEUM ETHER
    • 2.25e+01 g/L

  • Synonyms

    • AMINOPYRINE
    • aminophenazone
    • Amidopyrine
    • 58-15-1
    • 4-Dimethylaminoantipyrine
    • Dipyrine
    • Aminopyrin
    • Amidopyrazoline
    • Amidazophene
    • Pyramidon
    • Aminofenazone
    • Amidazophen
    • Amidophen
    • Brufaneuxol
    • Eufibron
    • Itamidone
    • Pyramidone
    • Dereuma
    • Febron
    • Dimethylaminoazophene
    • Amidophenazone
    • Aminophenazon
    • Dimethylaminoantipyrine
    • Amidofebrin
    • Amidofen
    • Amidopyrin
    • Anafebrina
    • Netsusarin
    • Dimethylaminophenazone
    • Amidazofen
    • Piromidina
    • Dimapyrin
    • Dipirin
    • Dipyrin
    • Febrinina
    • Hyparon
    • Novamidon
    • Piramidon
    • Pirazon
    • Piridol
    • Polinalin
    • Pyradone
    • 4-(Dimethylamino)antipyrine
    • Mamallet-A
    • 4-Dimethylaminophenazone
    • Amidazophenum
    • Aminofenazona
    • Aminopyrinum
    • 4-Dimethylamino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one
    • Dimethylamino-analgesine
    • Dimethylaminophenyldimethylpyrazolone
    • Dimethylaminophenazon
    • Aminopyrine [JAN]
    • Aminophenazonum
    • (Dimethylamino)phenazone
    • 4-(Dimethylamino)-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
    • Antipyrine, 4-(dimethylamino)-
    • 4-Dimethylamino-1-phenyl-2,3-dimethylpyrazolone
    • Aminofenazona [INN-Spanish]
    • Aminophenazonum [INN-Latin]
    • 3H-Pyrazol-3-one, 4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    • Aminophenazone [INN]
    • 1,5-Dimethyl-4-dimethylamino-2-phenyl-3-pyrazolone
    • 1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazol-5-one
    • 2,3-Dimethyl-4-dimethylamino-1-phenyl-5-pyrazolone
    • 4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone
    • CCRIS 2907
    • Aminopyrine [JAN:NF]
    • HSDB 2135
    • Mamallet a
    • Dimethylaminophenyldimethylpyrazolin
    • NSC 4993
    • EINECS 200-365-8
    • Aminopyrine (JAN)
    • UNII-01704YP3MO
    • Aminophenazone (INN)
    • DTXSID7020504
    • 3-Keto-1,5-dimethyl-4-dimethylamino-2-phenyl-2,3-dihydropyrazole
    • Dimethylaminophenyldimethylpyrazone
    • 1-Phenyl-2,3-dimethyl-4-(dimethylamino)-5-pyrazolone
    • NSC-4993
    • AMINOPYRINE [MI]
    • MFCD00003142
    • 4-Dimethylamino Antipyrine
    • AMINOPYRINE [HSDB]
    • 4-(Dimethylamino)phenazone
    • 3H-Pyrazol-3-one,4-(dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-
    • 4-(Dimethylamino)-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
    • 4-(dimethylamino)-1,5-dimethyl-2-phenylpyrazol-3-one
    • DTXCID70504
    • AMINOPHENAZONE [MART.]
    • MLS002154195
    • AMINOPHENAZONE [WHO-DD]
    • 3-Pyrazolin-5-one, 4-(dimethylamino)-2,3-dimethyl-1-phenyl-
    • CHEBI:160246
    • 01704YP3MO
    • CAS-58-15-1
    • NCGC00016257-04
    • Amidophenazon
    • Amidopyrinum
    • SMR001216566
    • 4-(dimethylamino)-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
    • Aminofenazona (INN-Spanish)
    • Aminophenazonum (INN-Latin)
    • 1-Phenyl-2,3-dimethyl-4-dimethylaminopyrazolone-5
    • 1,5-Dimethyl-2-phenyl-4-dimethylamino-3-pyrazolone
    • AMINOPHENAZONE (MART.)
    • Aminophenazon [German]
    • METAMIZOLE SODIUM MONOHYDRATE IMPURITY D [EP IMPURITY]
    • Aminofenazone [Italian]
    • Dimethyl-N-aminoantipyrine
    • 4-DIMETHYLAMINO-1,5-DIMETHYL-2-PHENYL-1,2-DIHYDRO-3H-PYRAZOL-3-ONE
    • Dimethylaminophenazon [German]
    • dimethylaminoanalgesine
    • SR-05000001741
    • Dimethyl N aminoantipyrine
    • Piramidone
    • METAMIZOLE SODIUM MONOHYDRATE IMPURITY D (EP IMPURITY)
    • Prestwick_14
    • Prestwick0_000088
    • Prestwick1_000088
    • Prestwick2_000088
    • Prestwick3_000088
    • cid_6009
    • TimTec1_000737
    • 3-keto-1,3-dihydropyrazole
    • Oprea1_080671
    • SCHEMBL26293

  • Applications

    Aminopyrine (CAS 58-15-1), also known as antipyrine, is primarily used in the pharmaceutical industry as an analgesic and antipyretic in historical or limited modern formulations, often appearing as a component in multi-ingredient preparations. In medicinal chemistry and drug development, aminopyrine is considered a chemical intermediate and building block for the synthesis of pyrazolone derivatives and related analgesic drugs. In laboratory and quality-control settings, it may serve as a reference compound for certain analyses involving pyrazolone medicines and as an analytical standard for measurement methods. In industrial chemical research, aminopyrine may be used as a starting material for synthesis routes related to pyrazolone chemistries. Its use is subject to local regulations and formulation limits due to safety concerns.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 597.32
    methanol 960.66
    isopropanol 363.96
    water 377.86
    ethyl acetate 280.76
    n-propanol 490.47
    acetone 485.72
    n-butanol 370.77
    acetonitrile 515.82
    DMF 595.04
    toluene 131.33
    isobutanol 347.93
    1,4-dioxane 606.6
    methyl acetate 345.82
    THF 580.56
    2-butanone 324.99
    n-pentanol 230.19
    sec-butanol 329.54
    n-hexane 10.85
    ethylene glycol 381.02
    NMP 428.1
    cyclohexane 36.71
    DMSO 383.18
    n-butyl acetate 144.87
    n-octanol 67.88
    chloroform 1717.59
    n-propyl acetate 139.84
    acetic acid 944.26
    dichloromethane 1575.99
    cyclohexanone 547.7
    propylene glycol 237.8
    isopropyl acetate 128.85
    DMAc 371.96
    2-ethoxyethanol 403.2
    isopentanol 247.4
    n-heptane 8.61
    ethyl formate 462.43
    1,2-dichloroethane 771.83
    n-hexanol 181.7
    2-methoxyethanol 884.71
    isobutyl acetate 90.82
    tetrachloromethane 275.04
    n-pentyl acetate 107.58
    transcutol 268.91
    n-heptanol 98.96
    ethylbenzene 69.47
    MIBK 113.62
    2-propoxyethanol 310.85
    tert-butanol 282.36
    MTBE 123.08
    2-butoxyethanol 180.32
    propionic acid 425.05
    o-xylene 85.54
    formic acid 932.56
    diethyl ether 187.39
    m-xylene 78.21
    p-xylene 108.12
    chlorobenzene 356.12
    dimethyl carbonate 166.42
    n-octane 5.73
    formamide 1193.4
    cyclopentanone 538.12
    2-pentanone 218.71
    anisole 120.68
    cyclopentyl methyl ether 221.24
    gamma-butyrolactone 721.01
    1-methoxy-2-propanol 400.86
    pyridine 553.8
    3-pentanone 194.78
    furfural 738.45
    n-dodecane 4.8
    diethylene glycol 348.5
    diisopropyl ether 36.54
    tert-amyl alcohol 240.55
    acetylacetone 227.77
    n-hexadecane 5.56
    acetophenone 151.59
    methyl propionate 256.53
    isopentyl acetate 118.43
    trichloroethylene 1482.02
    n-nonanol 58.95
    cyclohexanol 356.88
    benzyl alcohol 226.05
    2-ethylhexanol 83.99
    isooctanol 75.16
    dipropyl ether 56.02
    1,2-dichlorobenzene 309.43
    ethyl lactate 102.42
    propylene carbonate 425.95
    n-methylformamide 696.81
    2-pentanol 188.92
    n-pentane 14.84
    1-propoxy-2-propanol 148.13
    1-methoxy-2-propyl acetate 125.42
    2-(2-methoxypropoxy) propanol 83.12
    mesitylene 43.6
    ε-caprolactone 415.68
    p-cymene 41.73
    epichlorohydrin 838.77
    1,1,1-trichloroethane 603.58
    2-aminoethanol 510.28
    morpholine-4-carbaldehyde 459.18
    sulfolane 531.59
    2,2,4-trimethylpentane 9.58
    2-methyltetrahydrofuran 397.05
    n-hexyl acetate 118.36
    isooctane 5.5
    2-(2-butoxyethoxy)ethanol 124.74
    sec-butyl acetate 78.14
    tert-butyl acetate 104.23
    decalin 13.68
    glycerin 383.82
    diglyme 267.1
    acrylic acid 513.11
    isopropyl myristate 36.44
    n-butyric acid 521.26
    acetyl acetate 205.58
    di(2-ethylhexyl) phthalate 60.46
    ethyl propionate 128.08
    nitromethane 1012.53
    1,2-diethoxyethane 100.43
    benzonitrile 274.27
    trioctyl phosphate 43.96
    1-bromopropane 275.22
    gamma-valerolactone 723.96
    n-decanol 42.05
    triethyl phosphate 57.11
    4-methyl-2-pentanol 87.89
    propionitrile 344.78
    vinylene carbonate 511.11
    1,1,2-trichlorotrifluoroethane 602.7
    DMS 146.49
    cumene 48.73
    2-octanol 63.06
    2-hexanone 120.96
    octyl acetate 57.05
    limonene 54.34
    1,2-dimethoxyethane 382.16
    ethyl orthosilicate 52.9
    tributyl phosphate 52.22
    diacetone alcohol 155.51
    N,N-dimethylaniline 79.87
    acrylonitrile 490.77
    aniline 285.4
    1,3-propanediol 631.9
    bromobenzene 324.19
    dibromomethane 850.39
    1,1,2,2-tetrachloroethane 974.61
    2-methyl-cyclohexyl acetate 87.0
    tetrabutyl urea 63.04
    diisobutyl methanol 40.45
    2-phenylethanol 168.04
    styrene 84.32
    dioctyl adipate 57.09
    dimethyl sulfate 218.69
    ethyl butyrate 92.38
    methyl lactate 159.37
    butyl lactate 93.97
    diethyl carbonate 77.89
    propanediol butyl ether 121.95
    triethyl orthoformate 66.11
    p-tert-butyltoluene 35.3
    methyl 4-tert-butylbenzoate 105.37
    morpholine 629.37
    tert-butylamine 145.81
    n-dodecanol 31.1
    dimethoxymethane 404.84
    ethylene carbonate 427.71
    cyrene 150.46
    2-ethoxyethyl acetate 136.68
    2-ethylhexyl acetate 95.68
    1,2,4-trichlorobenzene 330.5
    4-methylpyridine 413.2
    dibutyl ether 46.56
    2,6-dimethyl-4-heptanol 40.45
    DEF 240.78
    dimethyl isosorbide 161.74
    tetrachloroethylene 871.79
    eugenol 122.53
    triacetin 102.8
    span 80 85.03
    1,4-butanediol 266.17
    1,1-dichloroethane 642.33
    2-methyl-1-pentanol 172.1
    methyl formate 651.11
    2-methyl-1-butanol 267.99
    n-decane 7.86
    butyronitrile 366.21
    3,7-dimethyl-1-octanol 54.28
    1-chlorooctane 40.05
    1-chlorotetradecane 16.22
    n-nonane 7.18
    undecane 6.05
    tert-butylcyclohexane 10.49
    cyclooctane 8.72
    cyclopentanol 416.08
    tetrahydropyran 423.87
    tert-amyl methyl ether 92.79
    2,5,8-trioxanonane 148.38
    1-hexene 46.64
    2-isopropoxyethanol 203.0
    2,2,2-trifluoroethanol 637.56
    methyl butyrate 192.71

    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