Secobarbital

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  • Identifiers

    CAS number
    76-73-3

    Molecular formula
    C12H18N2O3

    SMILES
    CCCC(C)C1(C(=O)NC(=O)NC1=O)CC=C

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Spicy 38.01%
    Herbal 36.1%
    Odorless 32.21%
    Mint 30.47%
    Cooling 25.11%
    Green 24.64%
    Woody 19.82%
    Fruity 18.05%
    Warm 17.1%
    Citrus 16.29%

     

    Flavor
    Bitter 60.94%
    Cedarleaf 21.37%
    Odorless 20.36%
    Lovage 19.63%
    Basil 19.5%
    Nitrile 19.49%
    Leaves 19.03%
    Broom 18.99%
    Heather 18.79%
    Herbal 18.62%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.0

    pKa est.
    7.43 (neutral)

    Molecular weight
    238.28 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    388°C

    Melting point expt.

    • 100 °C

    Flash point

    • 170.51 ˚C est.

    Solubility expt.

    • 550 mg/L
    • Very slightly sol in water; freely sol in alc, ether, in soln of /fixed/ alkali hydroxides and carbonates; sol in chloroform
    • Very lipid sol
    • Very slightly soluble in solvent hexane; 1 gram dissolves in approximately 8.5 ml of 0.5 N sodium hydroxide.
    • 1.21e+00 g/L

  • Synonyms

    • secobarbital
    • Quinalbarbitone
    • Secobarbitone
    • Seconal
    • Meballymal
    • Quinalbarbital
    • Evronal
    • Hypotrol
    • 76-73-3
    • Immenox
    • Meballymalum
    • Secobarbitalum
    • Somosal
    • (+-)-Secobarbital
    • Somatarax
    • Barbosec
    • Secobarbitale [DCIT]
    • Secobarbitalum [INN-Latin]
    • 5-ALLYL-5-(1-METHYLBUTYL)BARBITURIC ACID
    • Secobarbital cii
    • (RS)-Secobarbital
    • Seconal (TN)
    • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-
    • 5-Allyl-5-(1-methylbutyl)barbiturate
    • 5-Allyl-5-(1-methylbutyl)malonylurea
    • Barbituric acid, 5-allyl-5-(1-methylbutyl)-
    • HSDB 3182
    • Secobarbital [USP:INN]
    • 5-pentan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
    • EINECS 200-982-2
    • BRN 0225330
    • CHEBI:9073
    • (+/-)-Secobarbital
    • 1P7H87IN75
    • SECOBARBITAL [INN]
    • 5-Allyl-5-(1-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
    • SECOBARBITAL [HSDB]
    • SECOBARBITAL [VANDF]
    • Secobarbital sodium free acid
    • SECOBARBITAL [MART.]
    • SECOBARBITAL [USP-RS]
    • SECOBARBITAL [WHO-DD]
    • DTXSID6044145
    • 5-allyl-5-(1-methylbutyl)pyrimidine-2,4,6(1H,3H,5H)-trione
    • SECOBARBITAL [USP IMPURITY]
    • 5-(1-methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione
    • 5-24-09-00235 (Beilstein Handbook Reference)
    • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propen-1-yl)-
    • DEA No. 2315
    • Secobarbitale
    • Hyptran
    • SECOBARBITAL SODIUM FREE ACID [MI]
    • Secobarbital (USP:INN)
    • 5-(1-Methylbutyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione
    • 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-pyrimidine-2,4,6(1H,3H,5H)-trione
    • Sodium quinalbarbitone
    • Secobarbitalum (INN-Latin)
    • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-, (+-)-
    • SECOBARBITAL (MART.)
    • SECOBARBITAL (USP-RS)
    • SECOBARBITAL (USP IMPURITY)
    • 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-1,3-diazinane-2,4,6-trione
    • Secobarbital (1.0mg/ml in Methanol)
    • Secobarbital (1mg/ml in Acetonitrile)
    • (+/-)-Quinalbarbitone
    • Secobarbital suppository dosage form
    • Secobarbital (USP/INN)
    • (+-)-5-Allyl-5-(1-methylbutyl)-barbituric acid
    • UNII-1P7H87IN75
    • NCGC00247712-01
    • secobarbital-natrium
    • Hyptran (Salt/Mix)
    • Imesonal (Salt/Mix)
    • Trisomnin (Salt/Mix)
    • Immenoctal (Salt/Mix)
    • BARBITURIC ACID, 5-ALLYL-5-(1-METHYLBUTYL)-, (+-)-
    • CHEMBL447
    • (.+/-.))-Secobarbital
    • SCHEMBL80734
    • GTPL7615
    • DTXCID4024145
    • SCHEMBL11110602
    • Secobarbital, analytical standard
    • N05CA06
    • Secobarbital, 1mg/ml in Methanol
    • VFA24397
    • Secobarbital 0.1 mg/ml in Methanol
    • Secobarbital 1.0 mg/ml in Methanol
    • DB00418
    • 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-(1-methylbutyl)-5-(2-propenyl)-, (+-)-(9CI)
    • NS00010411
    • S0223
    • D00430
    • Q414788
    • Secobarbital suppository dosage form [DEA No. 2316]
    • pyrimidine-2,4,6(1H,3H,5H)-trione, 5-allyl-5-(1-methylbutyl)-
    • Secobarbital, United States Pharmacopeia (USP) Reference Standard
    • 2,4,6(1H,3H,5H)-Pyrimidinitrione, 5-(1-methylbutyl)-5-(2-propenyl)-
    • 5-(1-Methylbutyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinitrione
    • 200-982-2

  • Applications

    Secobarbital is primarily used as an active pharmaceutical ingredient in prescription sedative-hypnotic formulations and is a controlled short-to-intermediate-acting barbiturate; typical real-world applications include its use as a sedative-hypnotic component in medications, as a preanesthetic medication for certain procedures, support for pharmaceutical research and development (formulation development, pharmacology studies), use in analytical chemistry and quality control in the pharmaceutical sector (reference material for assay and stability testing), and regulated management of supply chains under local regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 30.4
    methanol 46.19
    isopropanol 23.95
    water 0.12
    ethyl acetate 26.01
    n-propanol 30.41
    acetone 55.54
    n-butanol 30.52
    acetonitrile 15.28
    DMF 241.1
    toluene 10.52
    isobutanol 22.6
    1,4-dioxane 41.75
    methyl acetate 32.86
    THF 236.91
    2-butanone 59.63
    n-pentanol 21.4
    sec-butanol 23.77
    n-hexane 0.34
    ethylene glycol 12.04
    NMP 326.4
    cyclohexane 0.47
    DMSO 250.04
    n-butyl acetate 23.58
    n-octanol 3.59
    chloroform 58.48
    n-propyl acetate 16.42
    acetic acid 42.74
    dichloromethane 57.91
    cyclohexanone 114.67
    propylene glycol 28.2
    isopropyl acetate 19.49
    DMAc 224.94
    2-ethoxyethanol 34.93
    isopentanol 26.66
    n-heptane 0.16
    ethyl formate 27.32
    1,2-dichloroethane 41.91
    n-hexanol 19.56
    2-methoxyethanol 88.62
    isobutyl acetate 12.71
    tetrachloromethane 5.23
    n-pentyl acetate 13.61
    transcutol 25.2
    n-heptanol 7.61
    ethylbenzene 5.23
    MIBK 29.06
    2-propoxyethanol 62.77
    tert-butanol 26.03
    MTBE 9.66
    2-butoxyethanol 23.75
    propionic acid 39.54
    o-xylene 7.79
    formic acid 24.95
    diethyl ether 7.87
    m-xylene 9.11
    p-xylene 7.81
    chlorobenzene 21.51
    dimethyl carbonate 22.4
    n-octane 0.1
    formamide 35.06
    cyclopentanone 221.67
    2-pentanone 47.69
    anisole 14.8
    cyclopentyl methyl ether 37.59
    gamma-butyrolactone 216.74
    1-methoxy-2-propanol 73.62
    pyridine 58.56
    3-pentanone 28.72
    furfural 125.8
    n-dodecane 0.12
    diethylene glycol 48.07
    diisopropyl ether 2.31
    tert-amyl alcohol 24.56
    acetylacetone 54.79
    n-hexadecane 0.14
    acetophenone 27.02
    methyl propionate 37.23
    isopentyl acetate 25.26
    trichloroethylene 102.53
    n-nonanol 3.89
    cyclohexanol 25.0
    benzyl alcohol 26.09
    2-ethylhexanol 8.85
    isooctanol 6.36
    dipropyl ether 3.86
    1,2-dichlorobenzene 22.08
    ethyl lactate 18.41
    propylene carbonate 86.45
    n-methylformamide 77.18
    2-pentanol 14.28
    n-pentane 0.29
    1-propoxy-2-propanol 31.82
    1-methoxy-2-propyl acetate 39.32
    2-(2-methoxypropoxy) propanol 25.49
    mesitylene 5.02
    ε-caprolactone 86.62
    p-cymene 4.33
    epichlorohydrin 180.91
    1,1,1-trichloroethane 29.24
    2-aminoethanol 27.58
    morpholine-4-carbaldehyde 133.06
    sulfolane 285.11
    2,2,4-trimethylpentane 0.43
    2-methyltetrahydrofuran 85.87
    n-hexyl acetate 14.91
    isooctane 0.32
    2-(2-butoxyethoxy)ethanol 22.43
    sec-butyl acetate 12.89
    tert-butyl acetate 25.49
    decalin 0.65
    glycerin 43.34
    diglyme 36.28
    acrylic acid 40.05
    isopropyl myristate 5.24
    n-butyric acid 52.42
    acetyl acetate 17.22
    di(2-ethylhexyl) phthalate 14.81
    ethyl propionate 17.45
    nitromethane 68.97
    1,2-diethoxyethane 7.9
    benzonitrile 27.54
    trioctyl phosphate 8.57
    1-bromopropane 13.4
    gamma-valerolactone 201.59
    n-decanol 2.92
    triethyl phosphate 12.64
    4-methyl-2-pentanol 10.2
    propionitrile 20.08
    vinylene carbonate 61.51
    1,1,2-trichlorotrifluoroethane 92.78
    DMS 21.89
    cumene 4.48
    2-octanol 4.18
    2-hexanone 25.0
    octyl acetate 8.06
    limonene 5.41
    1,2-dimethoxyethane 47.81
    ethyl orthosilicate 10.15
    tributyl phosphate 9.99
    diacetone alcohol 58.07
    N,N-dimethylaniline 12.75
    acrylonitrile 34.14
    aniline 25.22
    1,3-propanediol 45.58
    bromobenzene 18.1
    dibromomethane 30.6
    1,1,2,2-tetrachloroethane 77.12
    2-methyl-cyclohexyl acetate 20.6
    tetrabutyl urea 16.01
    diisobutyl methanol 4.68
    2-phenylethanol 26.86
    styrene 5.43
    dioctyl adipate 11.78
    dimethyl sulfate 62.78
    ethyl butyrate 15.08
    methyl lactate 38.52
    butyl lactate 17.45
    diethyl carbonate 11.38
    propanediol butyl ether 17.51
    triethyl orthoformate 11.1
    p-tert-butyltoluene 3.88
    methyl 4-tert-butylbenzoate 27.05
    morpholine 74.72
    tert-butylamine 7.57
    n-dodecanol 2.06
    dimethoxymethane 66.6
    ethylene carbonate 47.38
    cyrene 58.45
    2-ethoxyethyl acetate 19.66
    2-ethylhexyl acetate 18.65
    1,2,4-trichlorobenzene 32.48
    4-methylpyridine 63.75
    dibutyl ether 2.24
    2,6-dimethyl-4-heptanol 4.68
    DEF 57.24
    dimethyl isosorbide 63.13
    tetrachloroethylene 36.93
    eugenol 30.07
    triacetin 17.81
    span 80 21.29
    1,4-butanediol 17.12
    1,1-dichloroethane 31.29
    2-methyl-1-pentanol 23.12
    methyl formate 53.15
    2-methyl-1-butanol 25.93
    n-decane 0.17
    butyronitrile 24.56
    3,7-dimethyl-1-octanol 5.31
    1-chlorooctane 1.63
    1-chlorotetradecane 0.72
    n-nonane 0.12
    undecane 0.14
    tert-butylcyclohexane 0.59
    cyclooctane 0.18
    cyclopentanol 50.5
    tetrahydropyran 38.57
    tert-amyl methyl ether 11.77
    2,5,8-trioxanonane 30.15
    1-hexene 2.57
    2-isopropoxyethanol 23.73
    2,2,2-trifluoroethanol 19.58
    methyl butyrate 26.02

    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