Primidone

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  • Identifiers

    CAS number
    125-33-7

    Molecular formula
    C12H14N2O2

    SMILES
    CCC1(C(=O)NCNC1=O)C2=CC=CC=C2

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Spicy 34.47%
    Odorless 33.04%
    Sweet 25.36%
    Herbal 24.59%
    Bitter 23.19%
    Nutty 23.01%
    Mint 22.93%
    Burnt 22.37%
    Cooling 21.36%
    Fruity 19.75%

     

    Flavor
    Bitter 84.03%
    Cedarleaf 20.51%
    Lovage 20.16%
    Odorless 19.54%
    Nitrile 19.37%
    Basil 18.68%
    Broom 18.65%
    Sweet-like 18.62%
    Genet 18.58%
    Heather 18.51%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.9

    pKa est.
    7.38 (neutral)

    Molecular weight
    218.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    489°C

    Melting point expt.

    • 538 to 540 °F (NTP, 1992)
    • 281.5 °C
    • MP: 281-282 °C

    Flash point

    • 186.9 ˚C est.

    Solubility expt.

    • >32.7 [ug/mL] (The mean of the results at pH 7.4)
    • less than 1 mg/mL at 66 °F (NTP, 1992)
    • 500 mg/L (at 22 °C)
    • In water, 480 mg/L at 30 °C
    • Very slightly soluble in water
    • Very slightly soluble in most organic solvents
    • 1.04e+00 g/L

  • Synonyms

    • primidone
    • 125-33-7
    • Primaclone
    • Mysoline
    • Lepimidin
    • 2-Deoxyphenobarbital
    • Neurosyn
    • Liskantin
    • Mylepsinum
    • Lepsiral
    • Misodine
    • Mizodin
    • Mylepsin
    • Mysedon
    • Primidon
    • Sertan
    • 2-Desoxyphenobarbital
    • Hexadiona
    • Majsolin
    • Milepsin
    • Misolyne
    • Prilepsin
    • Primacone
    • Primakton
    • Primoline
    • Prysoline
    • Resimatil
    • Midone
    • Mizolin
    • Cyral
    • Medi-Pets
    • Primidona
    • Desoxyphenobarbitone
    • Pyrimidone Medi-pets
    • Primacione
    • Primidonum
    • 5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
    • 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione
    • 4,6(1H,5H)-Pyrimidinedione, 5-ethyldihydro-5-phenyl-
    • Roe 101
    • 5-Ethyldihydro-5-phenyl-4,6(1H,5H)-pyrimidinedione
    • Primidone (primaclone)
    • 5-Ethyl-5-phenylhexahydropyrimidine-4,6-dione
    • 5-ethyl-5-phenyldihydropyrimidine-4,6(1H,5H)-dione
    • NCI-C56360
    • CHEBI:8412
    • 5-Ethylhexahydro-4,6-dioxo-5-phenylpyrimidine
    • 5-Ethylhexahydro-5-phenylpyrimidine-4,6-dione
    • NSC 41701
    • NSC-41701
    • Primidone(Mysoline)
    • 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion
    • DTXSID7023510
    • 13AFD7670Q
    • 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6)
    • MFCD00038662
    • MLS000028593
    • DTXCID603510
    • Myidone
    • NSC41701
    • NCGC00015834-11
    • CAS-125-33-7
    • SMR000058501
    • PRIMIDONE (IARC)
    • PRIMIDONE [IARC]
    • PRIMIDONE (MART.)
    • PRIMIDONE [MART.]
    • PRIMIDONE (USP-RS)
    • PRIMIDONE [USP-RS]
    • Primidonum [INN-Latin]
    • Primidona [INN-Spanish]
    • PRIMIDONE (EP IMPURITY)
    • PRIMIDONE [EP IMPURITY]
    • PRIMIDONE (EP MONOGRAPH)
    • PRIMIDONE [EP MONOGRAPH]
    • PRIMIDONE (USP MONOGRAPH)
    • PRIMIDONE [USP MONOGRAPH]
    • Hexamidine (the antispasmodic)
    • CCRIS 54
    • Mysoline (TN)
    • HSDB 3169
    • SR-01000003162
    • EINECS 204-737-0
    • BRN 0218034
    • Hexamidine(the antispasmodic)
    • Primadon
    • 5-Aethyl-5-phenyl-hexahydropyrimidin-4,6-dion [German]
    • 5-Phenyl-5-aethylhexahydropyrimidindion-(4,6) [German]
    • UNII-13AFD7670Q
    • Mylepsin Tablets
    • Neurosyn Tablets
    • Primidone [USP:INN:BAN:JAN]
    • Primidonum (Latin)
    • HEXAMYDIN
    • Primidone (Mysoline)
    • Primidone (Standard)
    • Spectrum_000832
    • Tocris-0830
    • Pyrimidone 'Medi-pets'
    • A1AIA
    • Mysoline, Apo-Primidone
    • PRIMIDONE [INN]
    • PRIMIDONE [JAN]
    • PRIMIDONE [MI]
    • PRIMIDONE [HSDB]
    • Opera_ID_1083
    • Prestwick0_000933
    • Prestwick1_000933
    • Prestwick2_000933
    • Prestwick3_000933
    • Spectrum2_001293
    • Spectrum3_000553
    • Spectrum4_000485
    • Spectrum5_001144
    • Lopac-P-7295
    • PRIMIDONE [VANDF]
    • Biomol-NT_000261
    • CHEMBL856
    • P 7295
    • Pyrimidone ''Medi-pets''
    • PRIMIDONE [WHO-DD]
    • Lopac0_001021
    • SCHEMBL34221
    • BSPBio_000866
    • BSPBio_002225
    • KBioGR_000969
    • KBioSS_001312
    • 5-24-08-00102 (Beilstein Handbook Reference)

  • Applications

    Primidone (CAS 125-33-7) serves as an anticonvulsant active pharmaceutical ingredient (API) used in the treatment of epilepsy and is a prodrug that is metabolized to phenobarbital and other active metabolites. In pharmaceutical development, it is encountered as an API in formulations and as a reference compound for pharmacokinetic and analytical studies. It may be used as an intermediate in the synthesis of other barbiturate derivatives in chemical manufacturing. In research and laboratory settings, primidone is used for pharmacology investigations and method development for analytical assays. Its use is subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 24.55
    methanol 49.99
    isopropanol 17.66
    water 1.27
    ethyl acetate 18.0
    n-propanol 20.76
    acetone 32.06
    n-butanol 18.79
    acetonitrile 17.65
    DMF 199.11
    toluene 6.78
    isobutanol 14.4
    1,4-dioxane 44.81
    methyl acetate 20.08
    THF 63.96
    2-butanone 27.94
    n-pentanol 16.73
    sec-butanol 13.72
    n-hexane 0.31
    ethylene glycol 22.57
    NMP 141.47
    cyclohexane 0.45
    DMSO 167.62
    n-butyl acetate 14.63
    n-octanol 8.17
    chloroform 73.7
    n-propyl acetate 12.23
    acetic acid 38.49
    dichloromethane 73.07
    cyclohexanone 66.43
    propylene glycol 17.17
    isopropyl acetate 11.72
    DMAc 123.85
    2-ethoxyethanol 33.49
    isopentanol 15.56
    n-heptane 0.36
    ethyl formate 27.0
    1,2-dichloroethane 47.9
    n-hexanol 16.31
    2-methoxyethanol 69.84
    isobutyl acetate 8.47
    tetrachloromethane 6.41
    n-pentyl acetate 12.81
    transcutol 18.99
    n-heptanol 11.54
    ethylbenzene 4.86
    MIBK 16.52
    2-propoxyethanol 40.52
    tert-butanol 16.99
    MTBE 5.42
    2-butoxyethanol 23.19
    propionic acid 28.84
    o-xylene 6.53
    formic acid 35.38
    diethyl ether 7.16
    m-xylene 6.58
    p-xylene 6.74
    chlorobenzene 20.96
    dimethyl carbonate 22.84
    n-octane 0.32
    formamide 58.46
    cyclopentanone 90.07
    2-pentanone 24.13
    anisole 12.36
    cyclopentyl methyl ether 17.32
    gamma-butyrolactone 106.83
    1-methoxy-2-propanol 44.49
    pyridine 47.26
    3-pentanone 18.9
    furfural 90.08
    n-dodecane 0.49
    diethylene glycol 51.99
    diisopropyl ether 2.23
    tert-amyl alcohol 12.35
    acetylacetone 33.51
    n-hexadecane 0.57
    acetophenone 21.18
    methyl propionate 24.85
    isopentyl acetate 14.12
    trichloroethylene 94.31
    n-nonanol 8.12
    cyclohexanol 16.29
    benzyl alcohol 22.67
    2-ethylhexanol 8.7
    isooctanol 9.1
    dipropyl ether 5.04
    1,2-dichlorobenzene 21.78
    ethyl lactate 16.66
    propylene carbonate 49.7
    n-methylformamide 78.11
    2-pentanol 9.51
    n-pentane 0.29
    1-propoxy-2-propanol 20.55
    1-methoxy-2-propyl acetate 23.2
    2-(2-methoxypropoxy) propanol 18.88
    mesitylene 4.32
    ε-caprolactone 48.97
    p-cymene 5.16
    epichlorohydrin 85.07
    1,1,1-trichloroethane 22.37
    2-aminoethanol 30.47
    morpholine-4-carbaldehyde 92.57
    sulfolane 145.93
    2,2,4-trimethylpentane 0.39
    2-methyltetrahydrofuran 27.7
    n-hexyl acetate 15.87
    isooctane 0.35
    2-(2-butoxyethoxy)ethanol 19.63
    sec-butyl acetate 7.8
    tert-butyl acetate 12.41
    decalin 0.7
    glycerin 41.39
    diglyme 34.98
    acrylic acid 35.96
    isopropyl myristate 6.99
    n-butyric acid 34.38
    acetyl acetate 15.51
    di(2-ethylhexyl) phthalate 13.7
    ethyl propionate 13.13
    nitromethane 65.4
    1,2-diethoxyethane 9.25
    benzonitrile 29.81
    trioctyl phosphate 10.12
    1-bromopropane 12.25
    gamma-valerolactone 103.39
    n-decanol 6.51
    triethyl phosphate 11.02
    4-methyl-2-pentanol 7.21
    propionitrile 21.5
    vinylene carbonate 53.55
    1,1,2-trichlorotrifluoroethane 69.19
    DMS 19.85
    cumene 4.35
    2-octanol 6.92
    2-hexanone 16.63
    octyl acetate 9.82
    limonene 6.29
    1,2-dimethoxyethane 42.76
    ethyl orthosilicate 8.94
    tributyl phosphate 9.8
    diacetone alcohol 27.82
    N,N-dimethylaniline 11.58
    acrylonitrile 38.07
    aniline 18.52
    1,3-propanediol 40.2
    bromobenzene 16.25
    dibromomethane 37.19
    1,1,2,2-tetrachloroethane 66.82
    2-methyl-cyclohexyl acetate 14.63
    tetrabutyl urea 15.35
    diisobutyl methanol 5.41
    2-phenylethanol 22.82
    styrene 5.43
    dioctyl adipate 11.51
    dimethyl sulfate 48.13
    ethyl butyrate 11.13
    methyl lactate 31.82
    butyl lactate 15.0
    diethyl carbonate 10.06
    propanediol butyl ether 17.12
    triethyl orthoformate 9.83
    p-tert-butyltoluene 4.61
    methyl 4-tert-butylbenzoate 24.46
    morpholine 46.5
    tert-butylamine 7.11
    n-dodecanol 5.0
    dimethoxymethane 60.26
    ethylene carbonate 41.92
    cyrene 37.49
    2-ethoxyethyl acetate 17.23
    2-ethylhexyl acetate 11.43
    1,2,4-trichlorobenzene 27.35
    4-methylpyridine 37.7
    dibutyl ether 4.3
    2,6-dimethyl-4-heptanol 5.41
    DEF 39.33
    dimethyl isosorbide 34.9
    tetrachloroethylene 42.46
    eugenol 27.88
    triacetin 17.82
    span 80 18.68
    1,4-butanediol 19.65
    1,1-dichloroethane 27.68
    2-methyl-1-pentanol 14.73
    methyl formate 57.26
    2-methyl-1-butanol 14.23
    n-decane 0.67
    butyronitrile 21.8
    3,7-dimethyl-1-octanol 7.21
    1-chlorooctane 4.31
    1-chlorotetradecane 2.04
    n-nonane 0.5
    undecane 0.57
    tert-butylcyclohexane 0.64
    cyclooctane 0.23
    cyclopentanol 25.41
    tetrahydropyran 22.26
    tert-amyl methyl ether 6.13
    2,5,8-trioxanonane 28.58
    1-hexene 2.05
    2-isopropoxyethanol 20.0
    2,2,2-trifluoroethanol 27.13
    methyl butyrate 19.57

    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