Gramine

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  • Identifiers

    CAS number
    87-52-5

    Molecular formula
    C11H14N2

    SMILES
    CN(C)CC1=CNC2=CC=CC=C21

    Safety labels

    Corrosive
    Corrosive

  • Odor profile

    Fragrance
    Animal 38.79%
    Fruity 34.96%
    Cheesy 30.6%
    Grape 29.37%
    Fishy 28.95%
    Sweet 28.35%
    Ripe 27.61%
    Burnt 26.6%
    Roasted 23.18%
    Meaty 22.17%

     

    Flavor
    Bitter 46.64%
    Fruity 26.35%
    Mild 24.03%
    Green pepper 20.66%
    Syrup 20.58%
    Very strong 20.21%
    Tomato leaf 20.05%
    Carrot 20.01%
    Cedarleaf 19.83%
    Indole 19.82%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    1.8

    pKa est.
    7.35 (neutral)

    Molecular weight
    174.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    309°C

    Melting point expt.

    • 138 - 139 °C

    Flash point

    • 149.6 ˚C est.

  • Synonyms

    • Gramine
    • 87-52-5
    • 3-(Dimethylaminomethyl)indole
    • Donaxine
    • Donaxin
    • Gramin
    • 1-(1H-indol-3-yl)-N,N-dimethylmethanamine
    • 1H-Indole-3-methanamine, N,N-dimethyl-
    • beta-Dimethylaminomethylindole
    • N,N-Dimethyl-1H-indole-3-methanamine
    • 3-(N,N-Dimethylaminomethyl)indole
    • (1H-indol-3-ylmethyl)dimethylamine
    • 3-[(Dimethylamino)methyl]indole
    • FGQ8A78L14
    • DTXSID3058955
    • NSC-16892
    • N,N-Dimethyl-1H-indole-3-methylamine
    • CHEBI:28948
    • 3-((DIMETHYLAMINO)METHYL)INDOLE
    • 3-[Dimethylaminomethyl]indole
    • RefChem:144278
    • DTXCID5048552
    • 201-749-8
    • MFCD00005629
    • Indol-3-ylmethyldimethylamine
    • (1H-Indol-3-ylmethyl)-dimethyl-amine
    • (Indol-3-ylmethyl)dimethylamine
    • NSC 16892
    • 1-(1H-indol-3-yl)-N,N-dimethyl-methanamine
    • Indole, 3-[(dimethylamino)methyl]-
    • [(1H-indol-3-yl)methyl]dimethylamine
    • .beta.-Dimethylaminomethylindole
    • INDOLE, 3-((DIMETHYLAMINO)METHYL)-
    • 3-((Dimethylamino)methyl)-Indole
    • 3-[(Dimethylamino)methyl]-Indole
    • EINECS 201-749-8
    • UNII-FGQ8A78L14
    • AI3-52146
    • Prestwick_245
    • Gramine (Standard)
    • Gramine, 99%
    • Enamine_005691
    • GRAMINE [MI]
    • Prestwick0_000629
    • Prestwick1_000629
    • Prestwick2_000629
    • Prestwick3_000629
    • Oprea1_150946
    • SCHEMBL63578
    • b-(Dimethylaminomethyl)indole
    • BSPBio_000598
    • MLS002153919
    • beta -dimethylaminomethylindole
    • SCHEMBL928608
    • SPBio_002817
    • indole, 3-dimethylaminomethyl-
    • BPBio1_000658
    • CHEMBL254348
    • orb1300698
    • SCHEMBL6015904
    • SCHEMBL9754870
    • beta-(Dimethylaminomethyl)indole
    • SCHEMBL29351803
    • HY-N0166R
    • HMS1410C15
    • HMS1569N20
    • HMS2096N20
    • HMS2268O03
    • HMS3651E18
    • HMS5080F08
    • 3-Dimethylaminomethylindol (gramin)
    • HY-N0166
    • MSK40307
    • NSC16892
    • TNP00029
    • WLN: T56 BMJ D1N1&1
    • CCG-46378
    • EBC-44342
    • HB0305
    • s2304
    • SBB003799
    • STL146344
    • (1H-Indol-3-ylmethyl)-dimethylamine
    • AKOS001055234
    • FG39390
    • 1H-Indol-3-yl-N,N-dimethylmethanamine
    • CAS-87-52-5
    • IDI1_007926
    • NCGC00016343-01
    • NCGC00016343-02
    • NCGC00016343-03
    • NCGC00016343-04
    • NCGC00016343-05
    • NCGC00016343-13
    • NCGC00142364-01
    • NCGC00142364-02
    • NCGC00142364-03
    • (1H-indol-3-yl)-N,N-dimethylmethanamine
    • .BETA.-(DIMETHYLAMINOMETHYL)INDOLE
    • AC-15584
    • AS-11847
    • SMR000112262
    • ST023280
    • SY005107
    • 1H-Indol-3-yl-N,N-dimethylmethanamine #
    • DB-057006
    • CS-0007885
    • D0653
    • N,N-Dimethyl-1H-indole-3-methanamine, 9CI
    • NS00039200
    • SW196552-2
    • EN300-05999
    • C08304
    • AE-508/21133004
    • AE-641/04280037
    • F093159
    • Q420118
    • SR-01000636080
    • SR-01000636080-1
    • SR-01000636080-4
    • BRD-K26005076-001-03-7
    • BRD-K26005076-001-06-0
    • BRD-K26005076-001-12-8
    • Z56917380
    • InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H
    • 87-52-5

  • Applications

    Gramine (CAS 87-52-5) is an indole-based alkaloid bearing a dimethylaminomethyl group, commonly regarded as an intermediate and building block for the synthesis of indole-containing compounds in pharmaceutical research and specialty chemicals; in the fragrance industry, the compound or its derivatives may be explored as an odorant precursor or as a contributor to indole-type aroma notes; in cosmetics and personal care, it may be considered as a fragrance component or synthesis precursor for formulations of scented products; in industrial manufacturing, gramine is studied as a starting material for indole-based molecules and related specialty chemicals.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 98.09
    methanol 140.82
    isopropanol 52.8
    water 2.45
    ethyl acetate 51.84
    n-propanol 92.86
    acetone 76.78
    n-butanol 84.96
    acetonitrile 26.96
    DMF 212.56
    toluene 10.39
    isobutanol 76.67
    1,4-dioxane 97.46
    methyl acetate 64.24
    THF 155.94
    2-butanone 67.89
    n-pentanol 64.52
    sec-butanol 57.97
    n-hexane 2.79
    ethylene glycol 80.49
    NMP 114.38
    cyclohexane 3.3
    DMSO 86.49
    n-butyl acetate 46.81
    n-octanol 25.07
    chloroform 89.04
    n-propyl acetate 42.18
    acetic acid 114.17
    dichloromethane 61.83
    cyclohexanone 78.7
    propylene glycol 79.35
    isopropyl acetate 29.03
    DMAc 151.11
    2-ethoxyethanol 133.52
    isopentanol 64.4
    n-heptane 3.68
    ethyl formate 61.9
    1,2-dichloroethane 40.92
    n-hexanol 80.89
    2-methoxyethanol 209.99
    isobutyl acetate 43.73
    tetrachloromethane 16.54
    n-pentyl acetate 28.23
    transcutol 135.71
    n-heptanol 37.99
    ethylbenzene 9.27
    MIBK 30.09
    2-propoxyethanol 142.98
    tert-butanol 57.14
    MTBE 31.79
    2-butoxyethanol 75.48
    propionic acid 74.96
    o-xylene 10.2
    formic acid 83.63
    diethyl ether 27.57
    m-xylene 10.84
    p-xylene 14.57
    chlorobenzene 23.05
    dimethyl carbonate 34.87
    n-octane 2.09
    formamide 71.23
    cyclopentanone 115.3
    2-pentanone 48.71
    anisole 28.31
    cyclopentyl methyl ether 55.83
    gamma-butyrolactone 128.08
    1-methoxy-2-propanol 119.45
    pyridine 60.98
    3-pentanone 40.25
    furfural 122.6
    n-dodecane 1.64
    diethylene glycol 149.13
    diisopropyl ether 8.19
    tert-amyl alcohol 53.38
    acetylacetone 46.37
    n-hexadecane 1.78
    acetophenone 38.69
    methyl propionate 59.24
    isopentyl acetate 47.33
    trichloroethylene 88.39
    n-nonanol 23.62
    cyclohexanol 49.68
    benzyl alcohol 47.7
    2-ethylhexanol 43.29
    isooctanol 31.02
    dipropyl ether 26.85
    1,2-dichlorobenzene 24.3
    ethyl lactate 41.21
    propylene carbonate 82.76
    n-methylformamide 105.01
    2-pentanol 41.88
    n-pentane 2.77
    1-propoxy-2-propanol 77.46
    1-methoxy-2-propyl acetate 56.34
    2-(2-methoxypropoxy) propanol 54.64
    mesitylene 6.81
    ε-caprolactone 76.61
    p-cymene 11.84
    epichlorohydrin 117.48
    1,1,1-trichloroethane 34.36
    2-aminoethanol 107.59
    morpholine-4-carbaldehyde 130.78
    sulfolane 106.15
    2,2,4-trimethylpentane 3.14
    2-methyltetrahydrofuran 90.58
    n-hexyl acetate 35.02
    isooctane 1.88
    2-(2-butoxyethoxy)ethanol 72.26
    sec-butyl acetate 30.15
    tert-butyl acetate 27.38
    decalin 3.11
    glycerin 117.76
    diglyme 113.6
    acrylic acid 78.17
    isopropyl myristate 14.55
    n-butyric acid 96.05
    acetyl acetate 29.24
    di(2-ethylhexyl) phthalate 26.52
    ethyl propionate 36.45
    nitromethane 107.31
    1,2-diethoxyethane 40.68
    benzonitrile 32.4
    trioctyl phosphate 19.61
    1-bromopropane 22.51
    gamma-valerolactone 139.4
    n-decanol 18.46
    triethyl phosphate 26.08
    4-methyl-2-pentanol 26.9
    propionitrile 37.2
    vinylene carbonate 76.22
    1,1,2-trichlorotrifluoroethane 120.81
    DMS 35.14
    cumene 10.54
    2-octanol 21.29
    2-hexanone 41.61
    octyl acetate 21.76
    limonene 15.73
    1,2-dimethoxyethane 130.12
    ethyl orthosilicate 25.21
    tributyl phosphate 21.62
    diacetone alcohol 49.64
    N,N-dimethylaniline 25.21
    acrylonitrile 45.71
    aniline 33.55
    1,3-propanediol 114.79
    bromobenzene 17.76
    dibromomethane 35.58
    1,1,2,2-tetrachloroethane 77.0
    2-methyl-cyclohexyl acetate 39.59
    tetrabutyl urea 28.1
    diisobutyl methanol 17.58
    2-phenylethanol 52.45
    styrene 9.87
    dioctyl adipate 23.81
    dimethyl sulfate 46.57
    ethyl butyrate 36.27
    methyl lactate 52.93
    butyl lactate 37.42
    diethyl carbonate 28.67
    propanediol butyl ether 58.39
    triethyl orthoformate 30.27
    p-tert-butyltoluene 11.07
    methyl 4-tert-butylbenzoate 38.79
    morpholine 122.5
    tert-butylamine 30.73
    n-dodecanol 14.57
    dimethoxymethane 92.39
    ethylene carbonate 60.46
    cyrene 70.29
    2-ethoxyethyl acetate 43.0
    2-ethylhexyl acetate 38.15
    1,2,4-trichlorobenzene 33.78
    4-methylpyridine 47.1
    dibutyl ether 16.01
    2,6-dimethyl-4-heptanol 17.58
    DEF 66.28
    dimethyl isosorbide 74.78
    tetrachloroethylene 59.11
    eugenol 50.06
    triacetin 36.77
    span 80 47.87
    1,4-butanediol 69.46
    1,1-dichloroethane 37.66
    2-methyl-1-pentanol 57.8
    methyl formate 94.72
    2-methyl-1-butanol 70.8
    n-decane 2.47
    butyronitrile 39.42
    3,7-dimethyl-1-octanol 24.49
    1-chlorooctane 10.57
    1-chlorotetradecane 4.71
    n-nonane 2.33
    undecane 1.95
    tert-butylcyclohexane 3.3
    cyclooctane 1.5
    cyclopentanol 67.4
    tetrahydropyran 71.56
    tert-amyl methyl ether 29.68
    2,5,8-trioxanonane 81.53
    1-hexene 11.58
    2-isopropoxyethanol 85.8
    2,2,2-trifluoroethanol 56.27
    methyl butyrate 54.67

    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