Meprobamate

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  • Identifiers

    CAS number
    57-53-4

    Molecular formula
    C9H18N2O4

    SMILES
    CCCC(C)(COC(=O)N)COC(=O)N

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 45.11%
    Fruity 25.19%
    Savory 24.85%
    Sulfurous 24.57%
    Cooling 24.4%
    Cheesy 24.24%
    Sour 24.01%
    Mint 22.96%
    Tropical 22.43%
    Milky 20.56%

     

    Flavor
    Fruity 58.3%
    Green 33.56%
    Sweet 31.71%
    Tropical 28.25%
    Cheese 26.95%
    Berry 26.4%
    Pineapple 21.88%
    Fatty 21.64%
    Sour 21.19%
    Woody 21.02%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.7

    pKa est.
    6.29 (neutral)

    Molecular weight
    218.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    333°C

    Melting point expt.

    • 219 to 223 °F (NTP, 1992)
    • 105 °C

    Flash point

    • 176.19 ˚C est.

    Solubility expt.

    • less than 1 mg/mL at 68 °F (NTP, 1992)
    • 4700 mg/L (at 25 °C)
    • Very soluble in benzene, ethyl ether, ethanol
    • Easily forms supersaturated solution with hot water; freely soluble in most org solvents
    • Solubility in water: 0.34% (w/w) at 20 °C; 0.79% at 37 °C (w/w)
    • Slightly sol in ether; sol in alcohol and acetone.
    • In water, 3.3X10+3 mg/L at 25 °C
    • 2.47e+00 g/L

  • Synonyms

    • meprobamate
    • Equanil
    • Meprospan
    • Miltown
    • Meprocompren
    • Amepromat
    • Meprobam
    • Meprobamat
    • Meproban
    • Neuramate
    • Amosene
    • Mepriam
    • Tranmep
    • 57-53-4
    • Anastress
    • Anathylmon
    • Ayeramate
    • Biobamate
    • Crestanil
    • Despasmol
    • Dicandiol
    • Equatrate
    • Holbamate
    • Mepiosine
    • Meprindon
    • Meproleaf
    • Meprotabs
    • Metractyl
    • Metranquil
    • Miltamato
    • Anatimon
    • Andaksin
    • Andaxin
    • Aneural
    • Ansiatan
    • Ansiowas
    • Anxietil
    • Apascil
    • Arcoban
    • Artolon
    • Auxietil
    • Biobamat
    • Calmadin
    • Calmiren
    • Carbaxin
    • Cirponyl
    • Ecuanil
    • Enorden
    • Equitar
    • Estasil
    • Gadexyl
    • Harmonin
    • Ipsotian
    • Lepenil
    • Lepetown
    • Libiolan
    • Margonil
    • Mepantin
    • Mepavlon
    • Meposed
    • Mepranil
    • Meprocon
    • Meprodil
    • Meprosa
    • Meprosan
    • Meprosin
    • Meprotan
    • Meprotil
    • Meptran
    • Milprem
    • Miltaun
    • Ansil
    • Anural
    • Anzil
    • Arpon
    • Calmax
    • Cirpon
    • Cyrpon
    • Dapaz
    • Diron
    • Edenal
    • Epicur
    • Epikur
    • Erina
    • Hartol
    • Klort
    • Larten
    • Letyl
    • Mendel
    • Meprol
    • Kesso-Bamate
    • Mar-Bate
    • Meprocon CMC
    • Dormabrol
    • Equilium
    • Meprodiol
    • Atraxin
    • Bamate
    • Deprol
    • Diurnal
    • Diveron
    • Milpath
    • 3P Bamate
    • Meprovanmeprozine
    • Canquil-400
    • Equanil suspension
    • Meptranactylmilprem
    • Meprobamato
    • Meprotanum
    • Micrainin
    • Procalmidol
    • Procarbamide
    • Meprin
    • Mepro-analgesic
    • Cap-O-Tran
    • Fas-Cile 200
    • Equazine-M
    • Bamo 400
    • Diurnaldiverondormabrol
    • Nephentine
    • Pathibamate
    • Perequietil
    • Perquietil
    • Pertranquil
    • Procalmadiol
    • Procalmadol
    • Sedabamate
    • Sedoselecta

  • Applications

    Meprobamate (CAS 57-53-4) is primarily employed as an active pharmaceutical ingredient in anxiolytic and sedative formulations, administered orally as tablets or capsules. It is widely used as a reference standard and analytical material for quality control and toxicology testing (e.g., HPLC/GC). In academic research and pharmaceutical development, it is treated as a model carbamate compound to study CNS pharmacology and structure-activity relationships. Depending on local regulations, its use is subject to control and it may be evaluated for roles in organic synthesis contexts or as a reference in analytical method development.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 9.35
    methanol 27.0
    isopropanol 3.94
    water 10.09
    ethyl acetate 3.84
    n-propanol 4.35
    acetone 8.7
    n-butanol 2.64
    acetonitrile 2.92
    DMF 57.85
    toluene 1.12
    isobutanol 3.12
    1,4-dioxane 4.21
    methyl acetate 4.22
    THF 20.41
    2-butanone 4.93
    n-pentanol 2.51
    sec-butanol 2.68
    n-hexane 0.22
    ethylene glycol 16.39
    NMP 95.07
    cyclohexane 0.14
    DMSO 93.37
    n-butyl acetate 4.95
    n-octanol 1.82
    chloroform 4.94
    n-propyl acetate 3.27
    acetic acid 31.84
    dichloromethane 4.27
    cyclohexanone 12.84
    propylene glycol 20.81
    isopropyl acetate 3.66
    DMAc 91.5
    2-ethoxyethanol 15.9
    isopentanol 3.26
    n-heptane 0.17
    ethyl formate 8.77
    1,2-dichloroethane 2.89
    n-hexanol 3.39
    2-methoxyethanol 29.76
    isobutyl acetate 2.68
    tetrachloromethane 1.38
    n-pentyl acetate 3.06
    transcutol 15.76
    n-heptanol 2.75
    ethylbenzene 1.14
    MIBK 5.19
    2-propoxyethanol 19.17
    tert-butanol 7.39
    MTBE 2.41
    2-butoxyethanol 10.64
    propionic acid 14.04
    o-xylene 2.02
    formic acid 70.2
    diethyl ether 1.09
    m-xylene 1.8
    p-xylene 1.96
    chlorobenzene 1.82
    dimethyl carbonate 6.3
    n-octane 0.13
    formamide 37.05
    cyclopentanone 24.99
    2-pentanone 4.32
    anisole 3.25
    cyclopentyl methyl ether 4.9
    gamma-butyrolactone 36.05
    1-methoxy-2-propanol 18.11
    pyridine 4.94
    3-pentanone 3.39
    furfural 38.72
    n-dodecane 0.1
    diethylene glycol 28.05
    diisopropyl ether 0.77
    tert-amyl alcohol 5.87
    acetylacetone 12.76
    n-hexadecane 0.11
    acetophenone 7.95
    methyl propionate 5.58
    isopentyl acetate 6.2
    trichloroethylene 8.14
    n-nonanol 1.76
    cyclohexanol 2.72
    benzyl alcohol 6.19
    2-ethylhexanol 2.34
    isooctanol 2.42
    dipropyl ether 1.55
    1,2-dichlorobenzene 2.97
    ethyl lactate 8.64
    propylene carbonate 23.22
    n-methylformamide 26.22
    2-pentanol 1.49
    n-pentane 0.13
    1-propoxy-2-propanol 11.05
    1-methoxy-2-propyl acetate 11.3
    2-(2-methoxypropoxy) propanol 14.65
    mesitylene 1.48
    ε-caprolactone 15.25
    p-cymene 1.76
    epichlorohydrin 17.57
    1,1,1-trichloroethane 3.08
    2-aminoethanol 18.85
    morpholine-4-carbaldehyde 45.57
    sulfolane 78.32
    2,2,4-trimethylpentane 0.19
    2-methyltetrahydrofuran 6.58
    n-hexyl acetate 3.77
    isooctane 0.15
    2-(2-butoxyethoxy)ethanol 12.99
    sec-butyl acetate 2.37
    tert-butyl acetate 6.32
    decalin 0.23
    glycerin 44.62
    diglyme 18.77
    acrylic acid 19.0
    isopropyl myristate 1.54
    n-butyric acid 12.05
    acetyl acetate 5.69
    di(2-ethylhexyl) phthalate 5.91
    ethyl propionate 3.65
    nitromethane 33.25
    1,2-diethoxyethane 2.52
    benzonitrile 4.8
    trioctyl phosphate 3.64
    1-bromopropane 1.09
    gamma-valerolactone 43.67
    n-decanol 1.32
    triethyl phosphate 5.46
    4-methyl-2-pentanol 1.95
    propionitrile 2.21
    vinylene carbonate 19.24
    1,1,2-trichlorotrifluoroethane 41.51
    DMS 6.57
    cumene 1.36
    2-octanol 1.49
    2-hexanone 3.53
    octyl acetate 2.35
    limonene 1.78
    1,2-dimethoxyethane 15.37
    ethyl orthosilicate 4.25
    tributyl phosphate 4.13
    diacetone alcohol 16.74
    N,N-dimethylaniline 4.18
    acrylonitrile 4.97
    aniline 2.78
    1,3-propanediol 16.58
    bromobenzene 1.62
    dibromomethane 2.45
    1,1,2,2-tetrachloroethane 8.4
    2-methyl-cyclohexyl acetate 6.41
    tetrabutyl urea 6.62
    diisobutyl methanol 1.72
    2-phenylethanol 6.7
    styrene 1.02
    dioctyl adipate 3.83
    dimethyl sulfate 26.12
    ethyl butyrate 4.03
    methyl lactate 16.87
    butyl lactate 7.67
    diethyl carbonate 4.03
    propanediol butyl ether 13.04
    triethyl orthoformate 4.17
    p-tert-butyltoluene 1.75
    methyl 4-tert-butylbenzoate 12.88
    morpholine 6.89
    tert-butylamine 2.16
    n-dodecanol 0.97
    dimethoxymethane 12.44
    ethylene carbonate 12.75
    cyrene 29.71
    2-ethoxyethyl acetate 5.17
    2-ethylhexyl acetate 4.4
    1,2,4-trichlorobenzene 4.46
    4-methylpyridine 5.85
    dibutyl ether 0.84
    2,6-dimethyl-4-heptanol 1.72
    DEF 9.5
    dimethyl isosorbide 27.59
    tetrachloroethylene 6.18
    eugenol 12.64
    triacetin 8.17
    span 80 11.17
    1,4-butanediol 8.71
    1,1-dichloroethane 2.12
    2-methyl-1-pentanol 3.08
    methyl formate 24.13
    2-methyl-1-butanol 2.95
    n-decane 0.15
    butyronitrile 2.31
    3,7-dimethyl-1-octanol 2.18
    1-chlorooctane 0.58
    1-chlorotetradecane 0.28
    n-nonane 0.14
    undecane 0.12
    tert-butylcyclohexane 0.23
    cyclooctane 0.12
    cyclopentanol 5.57
    tetrahydropyran 1.93
    tert-amyl methyl ether 2.77
    2,5,8-trioxanonane 18.47
    1-hexene 0.58
    2-isopropoxyethanol 9.07
    2,2,2-trifluoroethanol 23.35
    methyl butyrate 5.78

    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