Mercaptopurine

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  • Identifiers

    CAS number
    50-44-2

    Molecular formula
    C5H4N4S

    SMILES
    C1=NC2=C(N1)C(=S)N=CN2

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 53.68%
    Burnt 39.21%
    Nutty 35.55%
    Sulfurous 28.35%
    Roasted 27.96%
    Cooked 25.38%
    Meaty 23.26%
    Pungent 23.0%
    Musty 20.11%
    Popcorn 20.11%

     

    Flavor
    Bitter 89.11%
    Odorless 29.16%
    Nutty 22.03%
    Bread crust 19.66%
    Cereal 19.01%
    Very strong 18.92%
    Indole 18.4%
    Rotten 18.17%
    Scallion 18.12%
    Nitrile 18.11%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.0

    pKa est.
    8.68 (weak base)

    Molecular weight
    152.18 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    606°C

    Melting point expt.

    • 313 dec °C
    • 308 °C (decomposes)
    • 313 °C

    Flash point

    • 235.07 ˚C est.

    Solubility expt.

    • 22.5 [ug/mL] (The mean of the results at pH 7.4)
    • 68500 mg/L
    • In water, 6848 mg/L at 30 °C
    • Insoluble in water
    • Soluble in boiling water (1 in 100)
    • Soluble in hot alcohol and dilute alkali solutions; slightly soluble in dilute sulfuric acid
    • Soluble in alkaline solutions (with decomposition), hot ethanol and ethanol (1 in 950); slightly soluble in dilute sulphuric acid; almost insoluble in water, acetone, chloroform and diethyl ether.
    • 7.35e-01 g/L

  • Synonyms

    • 6-Mercaptopurine
    • mercaptopurine
    • 50-44-2
    • Purinethol
    • Mercapurin
    • 6-Thiopurine
    • 7H-purine-6-thiol
    • Mercaleukin
    • Leukerin
    • Leupurin
    • 6-Thioxopurine
    • Ismipur
    • Mern
    • 6-Thiohypoxanthine
    • 6-Mercaptopurin
    • Puri-Nethol
    • 6-Purinethiol
    • Purinethiol
    • 6-MP
    • Purimethol
    • Purine-6-thiol
    • 3H-Purine-6-thiol
    • 9H-Purine-6-thiol
    • 6 MP
    • 1,9-dihydro-6H-purine-6-thione
    • Mercaleukim
    • Hypoxanthine, thio-
    • 1,7-Dihydro-6H-purine-6-thione
    • Mercaptopurine (6-MP)
    • Mercaptopurin
    • Mercaptopurina
    • Mercaptopurinum
    • Merkaptopuryna
    • Mercaptopurine anhydrous
    • Purine-6(1H)-thione
    • 1H-Purine-6(9H)-thione
    • 3,7-dihydropurine-6-thione
    • 6-Merkaptopurin
    • 6H-Purine-6-thione, 1,7-dihydro-
    • Purine, 6-mercapto-
    • 9H-Purine-6(1H)-thione
    • Xaluprine
    • 7-Mercapto-1,3,4,6-tetrazaindene
    • Mercaptopurine (anhydrous)
    • 1H-Purine, 6-mercapto-
    • NSC 755
    • NCI-C04886
    • NSC-755
    • U-4748
    • CCRIS 2761
    • HSDB 3235
    • UNII-PKK6MUZ20G
    • 3,7-dihydro-6H-purine-6-thione
    • PKK6MUZ20G
    • EINECS 200-037-4
    • 1,9-dihydropurine-6-thione
    • Purixan
    • CHEBI:2208
    • Mercaptopurine;6-MP
    • NSC755
    • DTXSID0020810
    • Mercaptopurine (INN)
    • Purinethol (TN)
    • 1H-purine-6(7H)-thione.
    • DTXCID00810
    • CHEBI:50667
    • 157930-11-5
    • Mercaptopurine (VAN)
    • Mercaptopurin [German]
    • 6 Mercaptopurine
    • 6 Thiopurine
    • Merkaptopuryna [Polish]
    • NSC-759614
    • 6 Thiohypoxanthine
    • 6-Merkaptopurin [Czech]
    • MERCAPTOPURINE [INN]
    • Mercaptopurinum [INN-Latin]
    • 6-MERCAPTOPURINE (IARC)
    • 6-MERCAPTOPURINE [IARC]
    • Mercaptopurina [INN-Spanish]
    • Purin-6-thiol, monohydrat
    • 6-Merkaptopurin, monohydrat
    • thiohypoxanthine
    • Purine-6-thiol, monohydrate
    • UNII-E7WED276I5
    • 1194-62-3
    • 6H-Purin-6-thion, monohydrat
    • MERCAPTOPURINE (MART.)
    • CCRIS 5819
    • MERCAPTOPURINE (USP-RS)
    • CAS-50-44-2
    • 6 Mercaptopurine Monohydrate
    • SMR000544948
    • Mercaptopurine, 6-
    • AZATHIOPRINE IMPURITY B (EP IMPURITY)
    • AZATHIOPRINE IMPURITY B [EP IMPURITY]
    • MERCAPTOPURINE (EP IMPURITY)
    • MERCAPTOPURINE (USP MONOGRAPH)
    • 7H-PURINE-6-THIOL MONOHYDRATE
    • SR-05000001925
    • 1,7-Dihydro-6H-purin-6-thion, monohydrat
    • AI3-25013
    • NCIMech_000025
    • 9H-Purin-6-yl hydrosulfide
    • EC 612-090-4
    • a thiopurine
    • MERCAPTOPURINE MONOHYDRATE (EP MONOGRAPH)
    • 1,7-dihydro-6H-purine-6-thione hydrate (1:1)
    • 157930-13-7
    • Mercaptopurine [USAN:USP:INN]
    • 6H-Purine-6-thione, 1,2,3,9-tetrahydro-, hydrate (1:1)
    • MFCD00233552
    • Azathioprine impurity B
    • Spectrum_000921
    • Mercaptopurinum (Latin)
    • Spectrum2_000060
    • Spectrum3_000491
    • Spectrum4_000857
    • Spectrum5_000950
    • M0063
    • H-Purine-6(1H)-thione
    • SCHEMBL3893
    • CHEMBL1425
    • 6-Mercaptopurine (Standard)
    • BSPBio_001981
    • KBioGR_001493
    • KBioGR_002363
    • KBioSS_001401

  • Applications

    Mercaptopurine (CAS 50-44-2) is an active pharmaceutical ingredient used in chemotherapy regimens and immunosuppressive applications; it is also employed in biochemical and biomedical research as a purine analog to study nucleotide metabolism and cell proliferation; it may serve as an analytical reference compound in method development and validation; it can function as an intermediate or building block in the synthesis of related purine derivatives in pharmaceutical research; all use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 14.12
    methanol 22.04
    isopropanol 10.69
    water 1.96
    ethyl acetate 6.53
    n-propanol 13.03
    acetone 16.49
    n-butanol 10.52
    acetonitrile 5.24
    DMF 75.34
    toluene 0.58
    isobutanol 8.45
    1,4-dioxane 5.73
    methyl acetate 6.91
    THF 37.69
    2-butanone 13.48
    n-pentanol 8.36
    sec-butanol 9.98
    n-hexane 0.2
    ethylene glycol 19.7
    NMP 50.37
    cyclohexane 0.11
    DMSO 87.61
    n-butyl acetate 4.76
    n-octanol 1.91
    chloroform 1.61
    n-propyl acetate 5.24
    acetic acid 19.68
    dichloromethane 2.5
    cyclohexanone 11.15
    propylene glycol 17.94
    isopropyl acetate 3.99
    DMAc 32.69
    2-ethoxyethanol 32.2
    isopentanol 7.96
    n-heptane 0.46
    ethyl formate 9.47
    1,2-dichloroethane 2.5
    n-hexanol 4.43
    2-methoxyethanol 56.8
    isobutyl acetate 2.67
    tetrachloromethane 0.44
    n-pentyl acetate 4.8
    transcutol 27.9
    n-heptanol 3.27
    ethylbenzene 0.38
    MIBK 5.78
    2-propoxyethanol 20.77
    tert-butanol 8.28
    MTBE 3.11
    2-butoxyethanol 13.37
    propionic acid 11.49
    o-xylene 0.53
    formic acid 29.45
    diethyl ether 4.3
    m-xylene 0.6
    p-xylene 0.59
    chlorobenzene 1.02
    dimethyl carbonate 6.65
    n-octane 0.19
    formamide 42.68
    cyclopentanone 25.95
    2-pentanone 11.86
    anisole 2.18
    cyclopentyl methyl ether 7.38
    gamma-butyrolactone 27.16
    1-methoxy-2-propanol 37.86
    pyridine 7.17
    3-pentanone 6.67
    furfural 26.82
    n-dodecane 0.14
    diethylene glycol 28.58
    diisopropyl ether 1.13
    tert-amyl alcohol 7.31
    acetylacetone 10.79
    n-hexadecane 0.15
    acetophenone 4.25
    methyl propionate 9.2
    isopentyl acetate 3.8
    trichloroethylene 3.79
    n-nonanol 2.06
    cyclohexanol 4.83
    benzyl alcohol 5.21
    2-ethylhexanol 2.69
    isooctanol 2.69
    dipropyl ether 3.99
    1,2-dichlorobenzene 1.02
    ethyl lactate 7.83
    propylene carbonate 10.42
    n-methylformamide 36.81
    2-pentanol 6.36
    n-pentane 0.24
    1-propoxy-2-propanol 13.72
    1-methoxy-2-propyl acetate 7.52
    2-(2-methoxypropoxy) propanol 10.65
    mesitylene 0.43
    ε-caprolactone 11.21
    p-cymene 0.74
    epichlorohydrin 21.3
    1,1,1-trichloroethane 1.23
    2-aminoethanol 22.52
    morpholine-4-carbaldehyde 34.17
    sulfolane 39.54
    2,2,4-trimethylpentane 0.15
    2-methyltetrahydrofuran 13.24
    n-hexyl acetate 3.9
    isooctane 0.11
    2-(2-butoxyethoxy)ethanol 14.37
    sec-butyl acetate 3.0
    tert-butyl acetate 3.78
    decalin 0.11
    glycerin 34.57
    diglyme 22.81
    acrylic acid 13.83
    isopropyl myristate 1.85
    n-butyric acid 13.7
    acetyl acetate 2.82
    di(2-ethylhexyl) phthalate 3.23
    ethyl propionate 4.87
    nitromethane 31.05
    1,2-diethoxyethane 6.77
    benzonitrile 3.73
    trioctyl phosphate 2.63
    1-bromopropane 1.66
    gamma-valerolactone 34.49
    n-decanol 1.69
    triethyl phosphate 3.12
    4-methyl-2-pentanol 3.21
    propionitrile 5.43
    vinylene carbonate 7.73
    1,1,2-trichlorotrifluoroethane 19.03
    DMS 3.77
    cumene 0.4
    2-octanol 2.11
    2-hexanone 6.62
    octyl acetate 2.7
    limonene 1.18
    1,2-dimethoxyethane 24.15
    ethyl orthosilicate 2.78
    tributyl phosphate 2.85
    diacetone alcohol 11.67
    N,N-dimethylaniline 2.21
    acrylonitrile 8.32
    aniline 3.39
    1,3-propanediol 27.8
    bromobenzene 0.6
    dibromomethane 1.46
    1,1,2,2-tetrachloroethane 3.14
    2-methyl-cyclohexyl acetate 3.29
    tetrabutyl urea 4.47
    diisobutyl methanol 1.85
    2-phenylethanol 3.95
    styrene 0.46
    dioctyl adipate 3.62
    dimethyl sulfate 14.02
    ethyl butyrate 5.24
    methyl lactate 15.3
    butyl lactate 7.33
    diethyl carbonate 3.44
    propanediol butyl ether 10.96
    triethyl orthoformate 4.19
    p-tert-butyltoluene 0.71
    methyl 4-tert-butylbenzoate 6.18
    morpholine 13.38
    tert-butylamine 3.03
    n-dodecanol 1.31
    dimethoxymethane 29.57
    ethylene carbonate 6.2
    cyrene 15.75
    2-ethoxyethyl acetate 8.38
    2-ethylhexyl acetate 2.84
    1,2,4-trichlorobenzene 1.59
    4-methylpyridine 5.4
    dibutyl ether 2.12
    2,6-dimethyl-4-heptanol 1.85
    DEF 14.23
    dimethyl isosorbide 15.4
    tetrachloroethylene 2.15
    eugenol 9.45
    triacetin 5.69
    span 80 7.61
    1,4-butanediol 15.12
    1,1-dichloroethane 1.76
    2-methyl-1-pentanol 5.9
    methyl formate 22.96
    2-methyl-1-butanol 8.12
    n-decane 0.2
    butyronitrile 6.0
    3,7-dimethyl-1-octanol 1.92
    1-chlorooctane 0.64
    1-chlorotetradecane 0.35
    n-nonane 0.17
    undecane 0.16
    tert-butylcyclohexane 0.12
    cyclooctane 0.07
    cyclopentanol 11.57
    tetrahydropyran 4.95
    tert-amyl methyl ether 3.27
    2,5,8-trioxanonane 18.21
    1-hexene 0.81
    2-isopropoxyethanol 16.29
    2,2,2-trifluoroethanol 11.81
    methyl butyrate 7.23

    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