Pyrimethamine

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  • Identifiers

    CAS number
    58-14-0

    Molecular formula
    C12H13ClN4

    SMILES
    CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Animal 40.96%
    Burnt 27.54%
    Roasted 25.75%
    Floral 25.33%
    Musty 25.2%
    Meaty 24.88%
    Grape 24.56%
    Odorless 23.45%
    Phenolic 22.96%
    Fatty 22.94%

     

    Flavor
    Bitter 64.21%
    Mild 27.53%
    Odorless 26.38%
    Roasted 25.47%
    Very strong 21.38%
    Indole 21.24%
    Scallion 21.0%
    Nitrile 20.87%
    Soybean 20.65%
    Bread crust 20.59%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.7

    pKa est.
    6.62 (neutral)

    Molecular weight
    248.71 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    589°C

    Melting point expt.

    • 451 to 453 °F (capillary) (NTP, 1992)
    • 233.5 °C
    • 233-234 °C (capillary); 240-242 °C (copper block)

    Flash point

    • 249.69 ˚C est.

    Solubility expt.

    • >37.3 [ug/mL] (The mean of the results at pH 7.4)
    • less than 0.1 mg/mL at 70 °F (NTP, 1992)
    • 121 mg/L
    • In water, 10 mg/L (temperature not specified)
    • Practically insoluble in water; slightly soluble in ethanol (about 9 g/L), in dilute HCl (about 5 g/L); soluble in boiling ethanol (about 25 g/L); Very sparingly soluble in propylene glycol and dimethylacetamide at 70 °C
    • 1.79e-01 g/L

  • Synonyms

    • pyrimethamine
    • 58-14-0
    • Daraprim
    • Chloridine
    • 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
    • Diaminopyritamin
    • Ethylpyrimidine
    • Pirimecidan
    • Pirimetamin
    • Pirimetamina
    • Chloridin
    • Chloridyn
    • Darachlor
    • Erbaprelina
    • Khloridin
    • Primethamine
    • Pyrimethamin
    • Malocid
    • Malocide
    • Tindurin
    • Pyrimethaminum
    • Darapram
    • Daraprime
    • Malacid
    • 5-(4-CHLOROPHENYL)-6-ETHYL-2,4-PYRIMIDINEDIAMINE
    • Pyremethamine
    • 2,4-Pyrimidinediamine, 5-(4-chlorophenyl)-6-ethyl-
    • Daraclor
    • Maloprim
    • 2,4-Diamino-5-(p-chlorophenyl)-6-ethylpyrimidine
    • TCMDC-125860
    • 2,4-Diamino-5-chlorophenyl-6-ethylpyrimidine
    • BW 50-63
    • 2,4-Diamino-5-(4-chlorophenyl)-6-ethylpyrimidine
    • RP 4753
    • NCI-C01683
    • 5-(4'-Chlorophenyl)-2,4-diamino-6-ethylpyrimidine
    • GNF-Pf-5586
    • WR 2978
    • Pirimetamina [INN-Spanish]
    • Pyrimethaminum [INN-Latin]
    • NSC-3061
    • 5-(4-Chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
    • CCRIS 546
    • 4753 R.P.
    • NSC 3061
    • EINECS 200-364-2
    • UNII-Z3614QOX8W
    • BRN 0219864
    • CHEBI:8673
    • Z3614QOX8W
    • DTXSID9021217
    • 2,4-Pyrimidinediamine, 5-(p-chlorophenyl)-6-ethyl-
    • AI3-25005
    • HSDB 8042
    • NSC3061
    • Pyrimidine, 2,4-diamino-5-(p-chlorophenyl)-6-ethyl-
    • TCMDC-123831
    • CHEMBL36
    • 5-(4-CHLORO-PHENYL)-6-ETHYL-PYRIMIDINE-2,4-DIAMINE
    • RP-4753
    • WR-2978
    • MLS000028606
    • MLS002701881
    • DTXCID601217
    • Pyrimethamine [USP:INN:BAN:JAN]
    • FANSIDAR COMPONENT PYRIMETHAMINE
    • CAS-58-14-0
    • NCGC00016256-08
    • SMR000058714
    • Tinduring
    • Pirimetamina [Spanish]
    • Pirimetamina (INN-Spanish)
    • Pyrimethaminum (INN-Latin)
    • PYRIMETHAMINE (IARC)
    • PYRIMETHAMINE [IARC]
    • CP6
    • PYRIMETHAMINE (MART.)
    • PYRIMETHAMINE [MART.]
    • 5-(4-chlorophenyl)-6-ethyl-pyrimidine-2,4-diamine
    • PYRIMETHAMINE (USP-RS)
    • PYRIMETHAMINE [USP-RS]
    • BRD9204
    • BRD-9204
    • Pyrimethamine (USP:INN:BAN:JAN)
    • PYRIMETHAMINE (EP MONOGRAPH)
    • PYRIMETHAMINE [EP MONOGRAPH]
    • PYRIMETHAMINE (USP MONOGRAPH)
    • PYRIMETHAMINE [USP MONOGRAPH]
    • Daraprim (TN)
    • Pyrimethamine (Pyr)
    • SR-01000003150
    • MFCD00057350
    • CRL-8131 & Pyrimethamine
    • CRL-8142 & Pyrimethamine
    • Lactoferrin B & Pyrimethamine
    • Lactoferrin H & Pyrimethamine
    • Pyrimethamine (JAN/USP/INN)
    • AZT + Pyrimethamine combination
    • EXR-101
    • 5-(p-chlorophenyl)-6-ethyl-2,4-diaminopyrimidine
    • Prestwick_504
    • 5-(4-chlorophenyl)-2,4-diamino-6-ethylpyrimidine
    • BW 5063
    • Daraclor (Salt/Mix)
    • Spectrum_000906
    • 4km0
    • CPD000058714
    • Pyrimethamine (Standard)
    • Opera_ID_1437
    • Prestwick0_000037
    • Prestwick1_000037
    • Prestwick2_000037
    • Prestwick3_000037
    • Spectrum2_000886
    • Spectrum3_001701
    • Spectrum4_000494
    • Spectrum5_001447
    • PYRIMETHAMINE [MI]
    • PYRIMETHAMINE [INN]
    • PYRIMETHAMINE [JAN]
    • cid_4993
    • NCIOpen2_008313
    • BIDD:PXR0173
    • SCHEMBL25129
    • BSPBio_000133
    • BSPBio_003282
    • KBioGR_001007

  • Applications

    Pyrimethamine (CAS 58-14-0) is primarily used in the pharmaceutical industry as an active pharmaceutical ingredient in antiparasitic drugs, and it also serves as a lead scaffold for antifolate drug design while acting as a reference standard in analytical method development. In pharmaceutical R&D, it is employed to study dihydrofolate reductase inhibition mechanisms and to support structure-activity relationship (SAR) optimization of related antifolate derivatives.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 5.08
    methanol 9.25
    isopropanol 2.21
    water 0.1
    ethyl acetate 5.1
    n-propanol 4.96
    acetone 6.76
    n-butanol 4.55
    acetonitrile 1.23
    DMF 57.67
    toluene 1.23
    isobutanol 3.67
    1,4-dioxane 6.25
    methyl acetate 3.16
    THF 38.83
    2-butanone 7.5
    n-pentanol 3.88
    sec-butanol 2.67
    n-hexane 0.04
    ethylene glycol 5.75
    NMP 50.1
    cyclohexane 0.03
    DMSO 105.33
    n-butyl acetate 6.63
    n-octanol 1.45
    chloroform 8.84
    n-propyl acetate 3.58
    acetic acid 11.85
    dichloromethane 8.47
    cyclohexanone 14.22
    propylene glycol 6.88
    isopropyl acetate 2.76
    DMAc 46.14
    2-ethoxyethanol 15.36
    isopentanol 4.13
    n-heptane 0.07
    ethyl formate 7.8
    1,2-dichloroethane 6.31
    n-hexanol 4.5
    2-methoxyethanol 38.1
    isobutyl acetate 2.92
    tetrachloromethane 1.27
    n-pentyl acetate 5.87
    transcutol 14.79
    n-heptanol 3.24
    ethylbenzene 0.66
    MIBK 4.91
    2-propoxyethanol 24.36
    tert-butanol 3.18
    MTBE 1.3
    2-butoxyethanol 14.11
    propionic acid 6.21
    o-xylene 0.93
    formic acid 13.03
    diethyl ether 1.32
    m-xylene 1.11
    p-xylene 0.94
    chlorobenzene 3.86
    dimethyl carbonate 8.87
    n-octane 0.04
    formamide 15.05
    cyclopentanone 33.55
    2-pentanone 6.97
    anisole 3.75
    cyclopentyl methyl ether 5.73
    gamma-butyrolactone 34.69
    1-methoxy-2-propanol 21.7
    pyridine 10.01
    3-pentanone 4.78
    furfural 42.74
    n-dodecane 0.04
    diethylene glycol 27.01
    diisopropyl ether 0.36
    tert-amyl alcohol 3.12
    acetylacetone 11.45
    n-hexadecane 0.05
    acetophenone 6.66
    methyl propionate 7.55
    isopentyl acetate 6.8
    trichloroethylene 17.43
    n-nonanol 1.69
    cyclohexanol 2.48
    benzyl alcohol 7.04
    2-ethylhexanol 2.88
    isooctanol 2.69
    dipropyl ether 1.83
    1,2-dichlorobenzene 4.61
    ethyl lactate 6.68
    propylene carbonate 17.63
    n-methylformamide 18.2
    2-pentanol 1.75
    n-pentane 0.03
    1-propoxy-2-propanol 13.68
    1-methoxy-2-propyl acetate 12.66
    2-(2-methoxypropoxy) propanol 11.18
    mesitylene 0.63
    ε-caprolactone 13.55
    p-cymene 1.21
    epichlorohydrin 40.09
    1,1,1-trichloroethane 4.19
    2-aminoethanol 9.76
    morpholine-4-carbaldehyde 36.03
    sulfolane 70.75
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 9.43
    n-hexyl acetate 4.81
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 12.63
    sec-butyl acetate 2.28
    tert-butyl acetate 3.89
    decalin 0.07
    glycerin 19.92
    diglyme 21.8
    acrylic acid 8.67
    isopropyl myristate 2.05
    n-butyric acid 10.86
    acetyl acetate 3.94
    di(2-ethylhexyl) phthalate 5.73
    ethyl propionate 3.77
    nitromethane 20.11
    1,2-diethoxyethane 4.23
    benzonitrile 6.08
    trioctyl phosphate 3.95
    1-bromopropane 1.81
    gamma-valerolactone 49.29
    n-decanol 1.31
    triethyl phosphate 4.96
    4-methyl-2-pentanol 1.5
    propionitrile 2.47
    vinylene carbonate 17.12
    1,1,2-trichlorotrifluoroethane 44.84
    DMS 6.26
    cumene 0.7
    2-octanol 1.65
    2-hexanone 5.1
    octyl acetate 3.24
    limonene 1.36
    1,2-dimethoxyethane 17.58
    ethyl orthosilicate 4.09
    tributyl phosphate 4.08
    diacetone alcohol 11.37
    N,N-dimethylaniline 3.04
    acrylonitrile 4.97
    aniline 5.27
    1,3-propanediol 13.39
    bromobenzene 2.94
    dibromomethane 4.27
    1,1,2,2-tetrachloroethane 14.1
    2-methyl-cyclohexyl acetate 5.94
    tetrabutyl urea 6.1
    diisobutyl methanol 1.47
    2-phenylethanol 8.38
    styrene 0.78
    dioctyl adipate 4.39
    dimethyl sulfate 26.5
    ethyl butyrate 4.66
    methyl lactate 14.18
    butyl lactate 9.02
    diethyl carbonate 4.2
    propanediol butyl ether 9.99
    triethyl orthoformate 4.54
    p-tert-butyltoluene 1.1
    methyl 4-tert-butylbenzoate 10.17
    morpholine 11.78
    tert-butylamine 0.99
    n-dodecanol 0.96
    dimethoxymethane 28.78
    ethylene carbonate 12.02
    cyrene 17.81
    2-ethoxyethyl acetate 9.75
    2-ethylhexyl acetate 5.15
    1,2,4-trichlorobenzene 7.47
    4-methylpyridine 8.81
    dibutyl ether 1.0
    2,6-dimethyl-4-heptanol 1.47
    DEF 10.2
    dimethyl isosorbide 22.04
    tetrachloroethylene 8.25
    eugenol 13.36
    triacetin 5.9
    span 80 9.31
    1,4-butanediol 5.53
    1,1-dichloroethane 3.33
    2-methyl-1-pentanol 3.96
    methyl formate 15.64
    2-methyl-1-butanol 4.1
    n-decane 0.06
    butyronitrile 3.35
    3,7-dimethyl-1-octanol 1.63
    1-chlorooctane 0.52
    1-chlorotetradecane 0.27
    n-nonane 0.05
    undecane 0.05
    tert-butylcyclohexane 0.08
    cyclooctane 0.02
    cyclopentanol 5.5
    tetrahydropyran 3.59
    tert-amyl methyl ether 1.78
    2,5,8-trioxanonane 16.14
    1-hexene 0.3
    2-isopropoxyethanol 7.97
    2,2,2-trifluoroethanol 8.65
    methyl butyrate 5.63

    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