Harmaline

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  • Identifiers

    CAS number
    304-21-2

    Molecular formula
    C13H14N2O

    SMILES
    CC1=NCCC2=C1NC3=C2C=CC(=C3)OC

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Roasted 44.14%
    Nutty 35.45%
    Burnt 31.92%
    Sweet 31.12%
    Earthy 29.99%
    Animal 27.33%
    Powdery 26.67%
    Musty 26.58%
    Fruity 23.53%
    Vanilla 22.62%

     

    Flavor
    Bitter 84.19%
    Cereal 21.72%
    Very strong 21.42%
    Indole 20.99%
    Roasted 20.75%
    Taco 19.97%
    Cedarleaf 19.82%
    Bread crust 19.79%
    Soybean 19.51%
    Parsley 19.5%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    8.72 (weak base)

    Molecular weight
    214.26 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    442°C

    Melting point expt.

    • 229-231 °C
    • 250 - 251 °C

    Flash point

    • 214.87 ˚C est.

    Solubility expt.

    • Slightly soluble in water, alcohol, ether; quite soluble in hot alcohol, dilute acids
    • Soluble in chloroform, pyridine
    • 30.6 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • harmaline
    • 304-21-2
    • Dihydroharmine
    • Harmidine
    • Armalin
    • 3,4-Dihydroharmine
    • O-Methylharmalol
    • Harmalol methyl ether
    • 7-methoxy-1-methyl-4,9-dihydro-3H-pyrido[3,4-b]indole
    • 3H-Pyrido[3,4-b]indole, 4,9-dihydro-7-methoxy-1-methyl-
    • 1-Methyl-7-methoxy-3,4-dihydro-beta-carboline
    • 3H-Pyrido(3,4-b)indole, 4,9-dihydro-7-methoxy-1-methyl-
    • CN58I4TOET
    • 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido(3,4-b)indole
    • DTXSID8041038
    • 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid(3,4-b)indole
    • 3,4-Dihydro-7-methoxy-1-methyl-9-pyrido(3,4-b)indole
    • NSC-407285
    • 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
    • CHEBI:28172
    • 7-METHOXY-1-METHYL-4,9-DIHYDRO-3H-PYRIDO(3,4-B)INDOLE
    • 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid[3,4-b]indole
    • RefChem:145263
    • DTXCID6021038
    • 206-152-6
    • Harmine, dihydro-
    • harmalin
    • MFCD00004955
    • NSC 407285
    • 7-Methoxy-1-methyl-4,9-dihydro-3H-beta-carboline
    • 7-methoxy-1-methyl-3,4-dihydro-2H-pyrido[3,4-b]indole
    • MLS000028746
    • CHEMBL340807
    • TNP00101
    • s4776
    • 3,4-Dihydro-7-methoxy-1-methyl-9H-pyrido[3,4-b]indole
    • SMR000058221
    • 7-methoxy-1-methyl-3,4-dihydrobeta-carboline
    • 1-Methyl-7-methoxy-3,4-dihydro-.beta.-carboline
    • SR-01000721899
    • EINECS 206-152-6
    • UNII-CN58I4TOET
    • BRN 0207310
    • Dihydroharmine;
    • Dihydro-Harmine
    • HSDB 7645
    • 3,4-b]indole
    • 3, 4-Dihydroharmine
    • Spectrum_000301
    • Opera_ID_665
    • HARMALINE [MI]
    • HARMALINE [HSDB]
    • Prestwick0_000610
    • Prestwick1_000610
    • Prestwick2_000610
    • Prestwick3_000610
    • Spectrum2_000411
    • Spectrum3_000720
    • Spectrum4_000824
    • Spectrum5_001452
    • HARMALINE [MART.]
    • 1-Methyl-7-methoxy-3,4-dihydro- beta-carboline
    • Oprea1_112644
    • BSPBio_000520
    • BSPBio_002539
    • KBioGR_001367
    • KBioSS_000781
    • MLS001148231
    • BIDD:ER0444
    • DivK1c_000950
    • SCHEMBL199260
    • SPECTRUM1500864
    • 7-methoxy-1-methyl-2H,3H,4H-pyrido[3,4-b]indole
    • SPBio_000362
    • SPBio_002739
    • BPBio1_000572
    • MEGxp0_001874
    • orb1700013
    • SCHEMBL3862598
    • SCHEMBL29626541
    • ACon1_000019
    • CHEBI:95328
    • GTPL13140
    • HMS502P12
    • KBio1_000950
    • KBio2_000781
    • KBio2_003349
    • KBio2_005917
    • KBio3_001759
    • NINDS_000950
    • HMS1921K22
    • HMS2233L23
    • HMS3371G17
    • HMS3885P22
    • HMS5083L06
    • MSK11050
    • BDBM50029799
    • CCG-38677
    • NSC407285
    • NSC789037
    • SBB003407
    • STL570451
    • AKOS015904564
    • AKOS026750619
    • DB13875
    • EBC-442045
    • FH52430
    • KS-5325
    • NSC-789037
    • SDCCGMLS-0066716.P001
    • IDI1_000950
    • NCGC00017221-01
    • NCGC00017221-02
    • NCGC00017221-03
    • NCGC00017221-04
    • NCGC00017221-05
    • NCGC00017221-06
    • NCGC00017221-07
    • NCGC00017221-10
    • NCGC00094867-01
    • NCGC00094867-02
    • NCGC00094867-03
    • NCGC00094867-04
    • NCGC00094867-05
    • NCGC00094867-06
    • AC-34436
    • LS-14204
    • 304-21-2

  • Applications

    Harmaline (CAS 304-21-2) is a beta-carboline alkaloid that is evaluated in pharmaceutical research and chemical synthesis as a pharmacological tool to assess biological activity and interactions related to MAO and receptors in experimental settings; it also serves as a precursor or intermediate for the synthesis of beta-carboline derivatives used in medicinal chemistry; in analytical science and method development, harmaline can be used as an analytical standard for LC-MS/GC methods to quantify beta-carbolines or related compounds, and thanks to its chemical properties it is considered part of synthetic libraries for exploring new compounds in research, with use governed by applicable regulations.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 17.31
    methanol 23.93
    isopropanol 11.56
    water 0.13
    ethyl acetate 32.59
    n-propanol 17.15
    acetone 45.96
    n-butanol 16.79
    acetonitrile 17.01
    DMF 123.19
    toluene 13.13
    isobutanol 14.65
    1,4-dioxane 84.35
    methyl acetate 43.59
    THF 120.36
    2-butanone 48.5
    n-pentanol 15.28
    sec-butanol 12.39
    n-hexane 0.89
    ethylene glycol 16.21
    NMP 99.19
    cyclohexane 1.47
    DMSO 139.91
    n-butyl acetate 41.38
    n-octanol 5.44
    chloroform 127.44
    n-propyl acetate 33.66
    acetic acid 49.37
    dichloromethane 126.18
    cyclohexanone 63.4
    propylene glycol 10.3
    isopropyl acetate 26.18
    DMAc 140.71
    2-ethoxyethanol 65.15
    isopentanol 20.37
    n-heptane 0.8
    ethyl formate 31.1
    1,2-dichloroethane 79.41
    n-hexanol 16.58
    2-methoxyethanol 81.83
    isobutyl acetate 30.5
    tetrachloromethane 16.67
    n-pentyl acetate 25.63
    transcutol 231.5
    n-heptanol 9.62
    ethylbenzene 10.36
    MIBK 27.18
    2-propoxyethanol 66.92
    tert-butanol 18.65
    MTBE 20.21
    2-butoxyethanol 40.0
    propionic acid 27.08
    o-xylene 12.52
    formic acid 39.25
    diethyl ether 19.62
    m-xylene 10.95
    p-xylene 16.97
    chlorobenzene 38.26
    dimethyl carbonate 38.03
    n-octane 0.42
    formamide 61.32
    cyclopentanone 90.72
    2-pentanone 31.51
    anisole 42.72
    cyclopentyl methyl ether 35.24
    gamma-butyrolactone 114.42
    1-methoxy-2-propanol 48.22
    pyridine 67.31
    3-pentanone 31.36
    furfural 149.81
    n-dodecane 0.52
    diethylene glycol 78.31
    diisopropyl ether 7.72
    tert-amyl alcohol 17.89
    acetylacetone 57.41
    n-hexadecane 0.62
    acetophenone 44.85
    methyl propionate 34.99
    isopentyl acetate 46.49
    trichloroethylene 177.19
    n-nonanol 6.54
    cyclohexanol 17.19
    benzyl alcohol 36.03
    2-ethylhexanol 14.13
    isooctanol 9.99
    dipropyl ether 14.02
    1,2-dichlorobenzene 44.66
    ethyl lactate 26.35
    propylene carbonate 61.07
    n-methylformamide 48.33
    2-pentanol 10.3
    n-pentane 0.79
    1-propoxy-2-propanol 39.72
    1-methoxy-2-propyl acetate 59.9
    2-(2-methoxypropoxy) propanol 55.93
    mesitylene 7.94
    ε-caprolactone 60.83
    p-cymene 10.92
    epichlorohydrin 159.08
    1,1,1-trichloroethane 58.88
    2-aminoethanol 20.25
    morpholine-4-carbaldehyde 147.52
    sulfolane 138.08
    2,2,4-trimethylpentane 1.22
    2-methyltetrahydrofuran 56.11
    n-hexyl acetate 26.0
    isooctane 0.83
    2-(2-butoxyethoxy)ethanol 64.83
    sec-butyl acetate 26.13
    tert-butyl acetate 32.83
    decalin 1.87
    glycerin 32.89
    diglyme 134.99
    acrylic acid 38.24
    isopropyl myristate 13.64
    n-butyric acid 33.92
    acetyl acetate 34.66
    di(2-ethylhexyl) phthalate 24.17
    ethyl propionate 30.69
    nitromethane 107.84
    1,2-diethoxyethane 55.5
    benzonitrile 39.54
    trioctyl phosphate 13.47
    1-bromopropane 23.65
    gamma-valerolactone 146.66
    n-decanol 5.42
    triethyl phosphate 29.11
    4-methyl-2-pentanol 10.55
    propionitrile 20.31
    vinylene carbonate 68.15
    1,1,2-trichlorotrifluoroethane 136.2
    DMS 53.6
    cumene 10.42
    2-octanol 5.51
    2-hexanone 32.57
    octyl acetate 17.04
    limonene 12.21
    1,2-dimethoxyethane 107.07
    ethyl orthosilicate 26.73
    tributyl phosphate 19.63
    diacetone alcohol 40.81
    N,N-dimethylaniline 29.32
    acrylonitrile 33.13
    aniline 31.05
    1,3-propanediol 30.43
    bromobenzene 37.38
    dibromomethane 60.48
    1,1,2,2-tetrachloroethane 125.22
    2-methyl-cyclohexyl acetate 35.63
    tetrabutyl urea 24.37
    diisobutyl methanol 9.88
    2-phenylethanol 35.38
    styrene 13.41
    dioctyl adipate 25.78
    dimethyl sulfate 79.28
    ethyl butyrate 30.83
    methyl lactate 32.07
    butyl lactate 27.35
    diethyl carbonate 30.9
    propanediol butyl ether 27.38
    triethyl orthoformate 30.57
    p-tert-butyltoluene 10.46
    methyl 4-tert-butylbenzoate 40.91
    morpholine 81.84
    tert-butylamine 10.13
    n-dodecanol 4.66
    dimethoxymethane 76.55
    ethylene carbonate 54.27
    cyrene 59.76
    2-ethoxyethyl acetate 57.46
    2-ethylhexyl acetate 39.05
    1,2,4-trichlorobenzene 60.56
    4-methylpyridine 56.07
    dibutyl ether 10.5
    2,6-dimethyl-4-heptanol 9.88
    DEF 45.08
    dimethyl isosorbide 87.9
    tetrachloroethylene 81.0
    eugenol 49.13
    triacetin 44.88
    span 80 33.69
    1,4-butanediol 15.91
    1,1-dichloroethane 47.18
    2-methyl-1-pentanol 20.83
    methyl formate 51.4
    2-methyl-1-butanol 18.6
    n-decane 0.69
    butyronitrile 19.02
    3,7-dimethyl-1-octanol 9.49
    1-chlorooctane 4.43
    1-chlorotetradecane 2.61
    n-nonane 0.53
    undecane 0.58
    tert-butylcyclohexane 1.81
    cyclooctane 0.62
    cyclopentanol 19.13
    tetrahydropyran 44.26
    tert-amyl methyl ether 18.67
    2,5,8-trioxanonane 98.24
    1-hexene 4.51
    2-isopropoxyethanol 43.07
    2,2,2-trifluoroethanol 38.76
    methyl butyrate 37.43

    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