N-methyl-L-tryptophan

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  • Identifiers

    CAS number
    526-31-8

    Molecular formula
    C12H14N2O2

    SMILES
    CN[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 60.85%
    Savory 35.22%
    Meaty 28.24%
    Cooked 27.42%
    Grape 25.8%
    Bitter 23.2%
    Milky 22.71%
    Fruity 21.91%
    Cheesy 19.48%
    Roasted 19.41%

     

    Flavor
    Bitter 72.72%
    Odorless 60.21%
    Mild 31.64%
    Bland 30.72%
    Sweet-like 22.75%
    Nitrile 20.55%
    Very mild 20.31%
    Yeast 19.98%
    Orange flower 19.23%
    Cedarleaf 18.98%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -0.5

    pKa est.
    6.62 (neutral)

    Molecular weight
    218.25 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    446°C

    Flash point

    • 231.93 ˚C est.

  • Synonyms

    • Abrine
    • N-Methyl-L-tryptophan
    • 526-31-8
    • (2S)-3-(1H-indol-3-yl)-2-(methylamino)propanoic acid
    • N-Methyl-L-tryptophane
    • P57TWL22IX
    • (2S)-3-(1H-indol-3-yl)-2-(methylazaniumyl)propanoate
    • RefChem:551401
    • 208-388-5
    • L-Abrine
    • Nalpha-Methyl-L-tryptophan
    • MFCD00005645
    • L-(+)-Abrine
    • methyl-l-tryptophan
    • N-Me-Trp-OH
    • N(alpha)-methyl-L-tryptophan
    • N-methyltryptophan
    • (S)-3-(1H-indol-3-yl)-2-methylaminopropionic acid
    • L-Tryptophan, N-methyl-
    • (2S)-3-indol-3-yl-2-(methylamino)propanoic acid
    • H-MeTrp-OH
    • N-Metil-L-triptofano
    • UNII-P57TWL22IX
    • N-methyl tryptophan
    • EINECS 208-388-5
    • L-Abrine, 99%
    • ABRINE [MI]
    • SCHEMBL18778
    • BIDD:ER0516
    • BIDD:GT0591
    • CHEMBL552941
    • orb1301555
    • SCHEMBL27819744
    • CHEBI:15334
    • HY-N1436
    • MFCD00064902
    • MSK159347
    • s5828
    • SBB012419
    • AKOS015853699
    • CCG-214812
    • EBC-617654
    • FM52417
    • NCGC00142581-01
    • AC-34880
    • AS-35305
    • ST066888
    • SY057298
    • A1489
    • CS-0016868
    • NS00043410
    • C02983
    • Nalpha-Methyl-L-tryptophan, analytical standard
    • Nalpha-Methyl-L-tryptophan, purum, >=98.0% (TLC)
    • Q23804375
    • E9M
    • 526-31-8

  • Applications

    N-methyl-L-tryptophan is primarily used as a non-natural amino acid building block in pharmaceutical and medicinal chemistry, providing a chiral starting material for the synthesis of peptide-based drugs and enzyme inhibitors. It is employed in peptide synthesis as an unusual tryptophan derivative to explore structure–activity relationships. In analytical and research settings, it can serve as a reference standard for methods profiling tryptophan-related compounds. It also functions as a substrate analogue in biocatalysis studies and as an intermediate for preparing protected or modified tryptophan derivatives in specialty chemical syntheses. Its use is typically subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.84
    methanol 15.31
    isopropanol 1.3
    water 10.7
    ethyl acetate 1.1
    n-propanol 2.23
    acetone 1.16
    n-butanol 1.98
    acetonitrile 0.26
    DMF 52.08
    toluene 0.1
    isobutanol 2.02
    1,4-dioxane 1.07
    methyl acetate 1.03
    THF 5.77
    2-butanone 2.03
    n-pentanol 2.49
    sec-butanol 2.25
    n-hexane 0.07
    ethylene glycol 29.14
    NMP 71.81
    cyclohexane 0.03
    DMSO 23.33
    n-butyl acetate 1.5
    n-octanol 0.32
    chloroform 0.29
    n-propyl acetate 1.27
    acetic acid 18.68
    dichloromethane 0.37
    cyclohexanone 4.5
    propylene glycol 18.47
    isopropyl acetate 1.05
    DMAc 110.08
    2-ethoxyethanol 29.61
    isopentanol 2.85
    n-heptane 0.08
    ethyl formate 1.67
    1,2-dichloroethane 0.4
    n-hexanol 2.58
    2-methoxyethanol 52.85
    isobutyl acetate 1.03
    tetrachloromethane 0.18
    n-pentyl acetate 1.18
    transcutol 29.73
    n-heptanol 1.51
    ethylbenzene 0.19
    MIBK 1.97
    2-propoxyethanol 19.04
    tert-butanol 2.6
    MTBE 0.65
    2-butoxyethanol 10.35
    propionic acid 7.83
    o-xylene 0.23
    formic acid 119.12
    diethyl ether 0.4
    m-xylene 0.21
    p-xylene 0.36
    chlorobenzene 0.18
    dimethyl carbonate 2.89
    n-octane 0.04
    formamide 128.84
    cyclopentanone 8.37
    2-pentanone 1.93
    anisole 0.78
    cyclopentyl methyl ether 1.69
    gamma-butyrolactone 12.42
    1-methoxy-2-propanol 24.76
    pyridine 1.29
    3-pentanone 1.76
    furfural 15.2
    n-dodecane 0.03
    diethylene glycol 45.62
    diisopropyl ether 0.31
    tert-amyl alcohol 4.16
    acetylacetone 3.47
    n-hexadecane 0.03
    acetophenone 2.44
    methyl propionate 2.56
    isopentyl acetate 2.46
    trichloroethylene 0.96
    n-nonanol 0.47
    cyclohexanol 1.75
    benzyl alcohol 2.83
    2-ethylhexanol 1.47
    isooctanol 1.56
    dipropyl ether 0.77
    1,2-dichlorobenzene 0.37
    ethyl lactate 6.24
    propylene carbonate 6.38
    n-methylformamide 21.09
    2-pentanol 1.47
    n-pentane 0.04
    1-propoxy-2-propanol 9.23
    1-methoxy-2-propyl acetate 5.07
    2-(2-methoxypropoxy) propanol 11.67
    mesitylene 0.21
    ε-caprolactone 6.17
    p-cymene 0.35
    epichlorohydrin 5.83
    1,1,1-trichloroethane 0.22
    2-aminoethanol 30.65
    morpholine-4-carbaldehyde 34.23
    sulfolane 32.87
    2,2,4-trimethylpentane 0.07
    2-methyltetrahydrofuran 2.42
    n-hexyl acetate 0.98
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 13.34
    sec-butyl acetate 1.1
    tert-butyl acetate 1.95
    decalin 0.06
    glycerin 78.97
    diglyme 18.2
    acrylic acid 13.0
    isopropyl myristate 0.55
    n-butyric acid 7.39
    acetyl acetate 0.89
    di(2-ethylhexyl) phthalate 2.42
    ethyl propionate 1.5
    nitromethane 12.8
    1,2-diethoxyethane 1.65
    benzonitrile 0.79
    trioctyl phosphate 1.37
    1-bromopropane 0.16
    gamma-valerolactone 19.34
    n-decanol 0.42
    triethyl phosphate 2.39
    4-methyl-2-pentanol 1.62
    propionitrile 0.38
    vinylene carbonate 4.18
    1,1,2-trichlorotrifluoroethane 23.44
    DMS 3.19
    cumene 0.27
    2-octanol 0.61
    2-hexanone 1.67
    octyl acetate 0.79
    limonene 0.44
    1,2-dimethoxyethane 11.78
    ethyl orthosilicate 2.24
    tributyl phosphate 1.58
    diacetone alcohol 10.05
    N,N-dimethylaniline 1.25
    acrylonitrile 0.91
    aniline 0.69
    1,3-propanediol 25.22
    bromobenzene 0.12
    dibromomethane 0.2
    1,1,2,2-tetrachloroethane 1.07
    2-methyl-cyclohexyl acetate 2.49
    tetrabutyl urea 2.81
    diisobutyl methanol 0.97
    2-phenylethanol 2.87
    styrene 0.16
    dioctyl adipate 1.38
    dimethyl sulfate 10.87
    ethyl butyrate 1.54
    methyl lactate 12.98
    butyl lactate 5.31
    diethyl carbonate 1.38
    propanediol butyl ether 9.27
    triethyl orthoformate 2.15
    p-tert-butyltoluene 0.32
    methyl 4-tert-butylbenzoate 4.81
    morpholine 3.08
    tert-butylamine 0.78
    n-dodecanol 0.37
    dimethoxymethane 8.46
    ethylene carbonate 2.88
    cyrene 20.34
    2-ethoxyethyl acetate 3.28
    2-ethylhexyl acetate 1.72
    1,2,4-trichlorobenzene 0.63
    4-methylpyridine 0.85
    dibutyl ether 0.3
    2,6-dimethyl-4-heptanol 0.97
    DEF 7.25
    dimethyl isosorbide 15.99
    tetrachloroethylene 1.22
    eugenol 8.38
    triacetin 3.94
    span 80 8.18
    1,4-butanediol 16.13
    1,1-dichloroethane 0.16
    2-methyl-1-pentanol 3.38
    methyl formate 8.08
    2-methyl-1-butanol 3.21
    n-decane 0.04
    butyronitrile 0.53
    3,7-dimethyl-1-octanol 0.7
    1-chlorooctane 0.09
    1-chlorotetradecane 0.07
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.06
    cyclooctane 0.02
    cyclopentanol 3.77
    tetrahydropyran 0.65
    tert-amyl methyl ether 1.26
    2,5,8-trioxanonane 16.82
    1-hexene 0.24
    2-isopropoxyethanol 12.76
    2,2,2-trifluoroethanol 15.81
    methyl butyrate 2.49

    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