Thioguanine

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  • Identifiers

    CAS number
    154-42-7

    Molecular formula
    C5H5N5S

    SMILES
    C1=NC2=C(N1)C(=S)N=C(N2)N

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Odorless 63.01%
    Burnt 29.53%
    Meaty 26.1%
    Cooked 25.16%
    Roasted 24.67%
    Nutty 21.89%
    Sulfurous 21.88%
    Bitter 19.96%
    Savory 19.93%
    Musty 17.01%

     

    Flavor
    Bitter 86.37%
    Odorless 35.11%
    Nutty 21.14%
    Bread crust 20.38%
    Very strong 19.6%
    Scallion 19.34%
    Nitrile 19.34%
    Cereal 19.27%
    Rotten 19.13%
    Indole 19.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    -0.1

    pKa est.
    9.12 (weak base)

    Molecular weight
    167.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    692°C

    Melting point expt.

    • greater than 680 °F (NTP, 1992)
    • >360 °C
    • GREATER THAN 360 °C
    • > 360 °C

    Flash point

    • 276.4 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 73 °F (NTP, 1992)
    • 36.3 mg/mL
    • INSOL IN WATER, ALCOHOL, CHLOROFORM; FREELY SOL IN DIL SOLUTIONS OF ALKALI HYDROXIDES
    • 8.34e-01 g/L
    • Readily soluble in dilute aqueous alkali. Insoluble in water, alcohol, or chloroform.

  • Synonyms

    • 6-Thioguanine
    • thioguanine
    • 154-42-7
    • Tioguanine
    • 2-Amino-6-mercaptopurine
    • 6-Mercaptoguanine
    • Tabloid
    • Lanvis
    • 2-Amino-6-purinethiol
    • Tioguanin
    • 2-Amino 6MP
    • 2-Aminopurin-6-thiol
    • 2-Aminopurine-6-thiol
    • 2-Aminopurine-6(1H)-thione
    • 2-Amino-9H-purine-6-thiol
    • Wellcome U3B
    • 6-Mercapto-2-aminopurine
    • 2-Amino-6-merkaptopurin
    • Tioguanina
    • Tioguaninum
    • 6-TG
    • 2-Thioguanine
    • Guanine, thio-
    • Thioguanine Anhydrous
    • 6H-Purine-6-thione, 2-amino-1,7-dihydro-
    • 2-amino-3,7-dihydropurine-6-thione
    • 2-Amino-1,7-dihydro-6H-purine-6-thione
    • Tioguaninum [INN-Latin]
    • 2-Amino-1,9-Dihydro-6h-Purine-6-Thione
    • NSC-752
    • BW 5071
    • Purine-6-thiol, 2-amino-
    • Thioguanine Hemihydrate
    • Purine-6(1H)-thione, 2-amino-
    • 6-Tioguanine
    • Tioguanina [INN-Spanish]
    • Tioguanine (INN)
    • Tioguanine [INN]
    • Lanvis (TN)
    • TG
    • Thioguanine, anhydrous
    • CCRIS 8997
    • THG
    • HSDB 2504
    • NSC 752
    • 2-Amino-1,7-dihydro-6H-purin-6-thion
    • X 27
    • Thioguanine [USAN:USP]
    • 2-amino-3,7-dihydro-6H-purine-6-thione
    • 2-amino-6,7-dihydro-3H-purine-6-thione
    • UNII-WIX31ZPX66
    • EINECS 205-827-2
    • CHEBI:9555
    • Tioguanine hemihydrate
    • DTXSID6023652
    • AI3-26078
    • THIOGUANINE [MI]
    • 2-amino-1,9-dihydropurine-6-thione
    • MFCD00233553
    • THIOGUANINE [HSDB]
    • CHEMBL727
    • TIOGUANINE [WHO-DD]
    • WIX31ZPX66
    • UNII-FTK8U1GZNX
    • DTXCID803652
    • NSC752
    • Thioguanine2-Amino-6-purinethiol
    • 2-amino-1H-purine-6(9H)-thione
    • NSC-76504
    • NCGC00094792-01
    • 2-Aminopurine-6-thiol hemihydrate
    • Tioguaninum (INN-Latin)
    • Tabloid (TN)
    • Thioguanine (USAN:USP)
    • 6 Thioguanine
    • Tioguanina (INN-Spanish)
    • 2-Amino-6-MP
    • 157646-93-0
    • THIOGUANINE [VANDF]
    • TIOGUANINE (MART.)
    • TIOGUANINE [MART.]
    • 2-Aminopurin-6-thiol [Czech]
    • 2 Amino 6 Purinethiol
    • THIOGUANINE (USP-RS)
    • THIOGUANINE [USP-RS]
    • Guanine, thio- (VAN)
    • 2-Amino-6-merkaptopurin [Czech]
    • THIOGUANINE [ORANGE BOOK]
    • CAS-154-42-7
    • DX4
    • SMR000857244
    • 2-Amino-6-mercaptopurine-13C2,15N
    • THIOGUANINE (USP IMPURITY)
    • THIOGUANINE [USP IMPURITY]
    • THIOGUANINE (USP MONOGRAPH)
    • THIOGUANINE [USP MONOGRAPH]
    • 1330266-29-9
    • 9H-Purine-6-thiol, 2-amino-
    • TIOGUANINE HEMIHYDRATE [WHO-DD]
    • SR-05000002077
    • 5580-03-0
    • 2-Amino-1,7-dihydro-6H-purin-6-thion [Czech]
    • Thioquanine
    • Wellcome Brand of Thioguanine
    • Tioguanine GlaxoSmithKline Brand
    • 6-thioguano-sine
    • Glaxo Wellcome Brand of Tioguanine
    • 6-TG/Thioguanine
    • Glaxo Wellcome Brand of Thioguanine
    • GlaxoSmithKline Brand of Tioguanine
    • GlaxoSmithKline Brand of Thioguanine
    • 6-TG/Thioguanine?
    • 6H-PURINE-6-THIONE, 2-AMINO-1,9-DIHYDRO-, HYDRATE (2:1)
    • Spectrum_000235
    • Spectrum2_000695
    • Spectrum3_000577
    • Spectrum4_000926
    • Spectrum5_001455
    • 6-Thioguanine (Standard)
    • purine antimetabolite: antimetabolite: inhibits nucleic acid replication
    • 2-Amino-6-mercapto-purin
    • 6-Thioguanine, >=98%
    • SCHEMBL3701
    • SCHEMBL5898
    • NCIOpen2_004153
    • BSPBio_001994
    • KBioGR_001452
    • KBioGR_002476

  • Applications

    Thioguanine, also known as 6-thioguanine, is primarily used as a pharmaceutical active ingredient in cancer chemotherapy regimens, especially for hematologic malignancies, reflecting its cytotoxic activity as a purine analog. It has also been used as an immunosuppressive agent in autoimmune treatment contexts. In research and development, it serves as a purine nucleobase analogue and a tool in medicinal chemistry and biochemistry studies of purine metabolism and enzyme interactions. It can function as a chemical precursor or intermediate in the synthesis of nucleotide analogs and related thiopurine compounds, and may be employed as a reference material for analytical method development in pharmaceutical laboratories, subject to regulatory and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.09
    methanol 0.14
    isopropanol 0.08
    water 0.09
    ethyl acetate 0.07
    n-propanol 0.13
    acetone 0.11
    n-butanol 0.13
    acetonitrile 0.05
    DMF 4.32
    toluene 0.01
    isobutanol 0.1
    1,4-dioxane 0.09
    methyl acetate 0.13
    THF 0.81
    2-butanone 0.19
    n-pentanol 0.13
    sec-butanol 0.11
    n-hexane 0.0
    ethylene glycol 1.26
    NMP 6.64
    cyclohexane 0.0
    DMSO 15.01
    n-butyl acetate 0.41
    n-octanol 0.15
    chloroform 0.05
    n-propyl acetate 0.17
    acetic acid 0.35
    dichloromethane 0.05
    cyclohexanone 0.28
    propylene glycol 1.05
    isopropyl acetate 0.07
    DMAc 5.06
    2-ethoxyethanol 1.29
    isopentanol 0.13
    n-heptane 0.01
    ethyl formate 0.29
    1,2-dichloroethane 0.04
    n-hexanol 0.22
    2-methoxyethanol 2.66
    isobutyl acetate 0.12
    tetrachloromethane 0.02
    n-pentyl acetate 0.33
    transcutol 1.1
    n-heptanol 0.25
    ethylbenzene 0.01
    MIBK 0.14
    2-propoxyethanol 2.57
    tert-butanol 0.12
    MTBE 0.03
    2-butoxyethanol 1.87
    propionic acid 0.33
    o-xylene 0.01
    formic acid 1.38
    diethyl ether 0.02
    m-xylene 0.01
    p-xylene 0.02
    chlorobenzene 0.02
    dimethyl carbonate 0.34
    n-octane 0.0
    formamide 1.42
    cyclopentanone 1.11
    2-pentanone 0.14
    anisole 0.07
    cyclopentyl methyl ether 0.12
    gamma-butyrolactone 1.96
    1-methoxy-2-propanol 1.87
    pyridine 0.12
    3-pentanone 0.1
    furfural 3.25
    n-dodecane 0.0
    diethylene glycol 4.68
    diisopropyl ether 0.01
    tert-amyl alcohol 0.15
    acetylacetone 0.26
    n-hexadecane 0.01
    acetophenone 0.25
    methyl propionate 0.21
    isopentyl acetate 0.44
    trichloroethylene 0.12
    n-nonanol 0.17
    cyclohexanol 0.06
    benzyl alcohol 0.17
    2-ethylhexanol 0.18
    isooctanol 0.22
    dipropyl ether 0.12
    1,2-dichlorobenzene 0.04
    ethyl lactate 0.9
    propylene carbonate 0.95
    n-methylformamide 1.31
    2-pentanol 0.06
    n-pentane 0.0
    1-propoxy-2-propanol 1.76
    1-methoxy-2-propyl acetate 0.77
    2-(2-methoxypropoxy) propanol 1.85
    mesitylene 0.01
    ε-caprolactone 0.52
    p-cymene 0.05
    epichlorohydrin 1.05
    1,1,1-trichloroethane 0.03
    2-aminoethanol 0.97
    morpholine-4-carbaldehyde 4.11
    sulfolane 8.11
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.21
    n-hexyl acetate 0.29
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 1.79
    sec-butyl acetate 0.09
    tert-butyl acetate 0.13
    decalin 0.0
    glycerin 5.15
    diglyme 2.74
    acrylic acid 0.57
    isopropyl myristate 0.15
    n-butyric acid 0.38
    acetyl acetate 0.06
    di(2-ethylhexyl) phthalate 0.51
    ethyl propionate 0.18
    nitromethane 0.98
    1,2-diethoxyethane 0.16
    benzonitrile 0.16
    trioctyl phosphate 0.45
    1-bromopropane 0.02
    gamma-valerolactone 2.84
    n-decanol 0.13
    triethyl phosphate 0.48
    4-methyl-2-pentanol 0.06
    propionitrile 0.09
    vinylene carbonate 0.69
    1,1,2-trichlorotrifluoroethane 3.78
    DMS 0.31
    cumene 0.02
    2-octanol 0.15
    2-hexanone 0.23
    octyl acetate 0.24
    limonene 0.05
    1,2-dimethoxyethane 1.29
    ethyl orthosilicate 0.34
    tributyl phosphate 0.43
    diacetone alcohol 0.78
    N,N-dimethylaniline 0.11
    acrylonitrile 0.21
    aniline 0.05
    1,3-propanediol 0.98
    bromobenzene 0.01
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.15
    2-methyl-cyclohexyl acetate 0.33
    tetrabutyl urea 0.76
    diisobutyl methanol 0.11
    2-phenylethanol 0.3
    styrene 0.01
    dioctyl adipate 0.33
    dimethyl sulfate 2.04
    ethyl butyrate 0.3
    methyl lactate 1.52
    butyl lactate 1.15
    diethyl carbonate 0.28
    propanediol butyl ether 1.62
    triethyl orthoformate 0.39
    p-tert-butyltoluene 0.05
    methyl 4-tert-butylbenzoate 0.93
    morpholine 0.26
    tert-butylamine 0.03
    n-dodecanol 0.1
    dimethoxymethane 0.77
    ethylene carbonate 0.42
    cyrene 3.29
    2-ethoxyethyl acetate 0.47
    2-ethylhexyl acetate 0.32
    1,2,4-trichlorobenzene 0.08
    4-methylpyridine 0.12
    dibutyl ether 0.08
    2,6-dimethyl-4-heptanol 0.11
    DEF 0.5
    dimethyl isosorbide 3.68
    tetrachloroethylene 0.09
    eugenol 1.79
    triacetin 0.52
    span 80 1.22
    1,4-butanediol 0.6
    1,1-dichloroethane 0.02
    2-methyl-1-pentanol 0.13
    methyl formate 0.92
    2-methyl-1-butanol 0.13
    n-decane 0.01
    butyronitrile 0.1
    3,7-dimethyl-1-octanol 0.14
    1-chlorooctane 0.03
    1-chlorotetradecane 0.02
    n-nonane 0.0
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.0
    cyclopentanol 0.22
    tetrahydropyran 0.04
    tert-amyl methyl ether 0.06
    2,5,8-trioxanonane 2.54
    1-hexene 0.01
    2-isopropoxyethanol 0.6
    2,2,2-trifluoroethanol 0.65
    methyl butyrate 0.33

    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