Doxylamine

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  • Identifiers

    CAS number
    469-21-6

    Molecular formula
    C17H22N2O

    SMILES
    CC(C1=CC=CC=C1)(C2=CC=CC=N2)OCCN(C)C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 43.01%
    Sweet 36.08%
    Fruity 33.08%
    Fresh 27.39%
    Green 27.0%
    Animal 26.43%
    Earthy 26.2%
    Grapefruit 25.47%
    Woody 25.18%
    Grape 22.97%

     

    Flavor
    Green 49.26%
    Fruity 39.33%
    Earthy 34.73%
    Bitter 27.51%
    Pepper 22.27%
    Herbal 21.62%
    Mild 21.55%
    Floral 21.13%
    Musty 20.89%
    Green pepper 20.48%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.5

    pKa est.
    6.12 (neutral)

    Molecular weight
    270.37 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • < 25 °C
    • CRYSTALS; MP: 100-104 °C; 1% AQ SOLN HAS PH BETWEEN 4.9 & 5.1 /SUCCINATE/

    Boiling point

    • 279 to 286 °F at 0.5 mmHg (NTP, 1992)
    • 139 °C at 5.00E-01 mm Hg
    • 137-141 °C @ 0.5 MM HG

    Flash point

    • 160.91 ˚C est.

    Solubility expt.

    • 1 g/ml (succinate salt)
    • 1 G DISSOLVES IN 1 ML WATER; 1 G DISSOLVES IN 2 ML ALCOHOL; SLIGHTLY SOL IN BENZENE & ETHER; 1 G DISSOLVES IN 2 ML CHLOROFORM /SUCCINATE/
    • Soluble in acids.

  • Synonyms

    • doxylamine
    • 469-21-6
    • Dossilamina
    • Doxylaminum
    • Doxilminio
    • doxilamina
    • 2-Dimethylaminoethoxyphenylmethyl-2-picoline
    • dimethyl({2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethyl})amine
    • N,N-Dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)ethanamine
    • Phenyl-2-pyridylmethyl-beta-N,N-dimethylaminoethyl ether
    • 2-(alpha-(2-(Dimethylamino)ethoxy)-alpha-methylbenzyl)pyridine
    • 95QB77JKPL
    • Ethanamine, N,N-dimethyl-2-(1-phenyl-1-(2-pyridinyl)ethoxy)-
    • DTXSID1022970
    • CHEBI:51380
    • Ethanamine, N,N-dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]-
    • Pyridine, 2-(alpha-(2-(dimethylamino)ethoxy)-alpha-methylbenzyl)-
    • dimethyl((2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethyl))amine
    • (+-)-Doxylamine
    • RefChem:55070
    • DTXCID102970
    • R06AA09
    • 207-414-2
    • R-Doxylamine
    • (+/-)-Doxylamine
    • N,N-dimethyl-2-(1-phenyl-1-pyridin-2-ylethoxy)ethanamine
    • NCI C60684
    • Doxylamine (INN)
    • Doxylaminephenyl-d5
    • S-Doxylamine
    • Dossilamina [DCIT]
    • Alsadorm
    • Doxylaminum [INN-Latin]
    • Doxilminio [INN-Spanish]
    • Decapryn (TN)
    • DOXYLAMINE [INN]
    • Doxylamine [INN:BAN]
    • Pyridine, 2-[.alpha.-[2-(dimethylamino)ethoxy]-.alpha.-methylbenzyl]-
    • HSDB 5184
    • EINECS 207-414-2
    • UNII-95QB77JKPL
    • BRN 0230379
    • ()-Doxylamine
    • PYRIDINE, 2-(.ALPHA.-(2-(DIMETHYLAMINO)ETHOXY)-.ALPHA.-METHYLBENZYL)-
    • N,N-Dimethyl-2-[(1S)-1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine; (S)-N,N-Dimethyl-2-(1-phenyl-1-(pyridin-2-yl)ethoxy)ethanamine
    • Spectrum_001014
    • N,N-dimethyl-2-[1-phenyl-1-(pyridin-2-yl)ethoxy]ethanamine
    • DOXYLAMINE [MI]
    • Prestwick0_000027
    • Prestwick1_000027
    • Prestwick2_000027
    • Prestwick3_000027
    • Spectrum2_000115
    • Spectrum3_000409
    • Spectrum4_000528
    • Spectrum5_000949
    • DOXYLAMINE [HSDB]
    • DOXYLAMINE [VANDF]
    • EC 207-414-2
    • SCHEMBL4709
    • CHEMBL1004
    • DOXYLAMINE [WHO-DD]
    • Lopac0_000348
    • BSPBio_000093
    • BSPBio_001938
    • KBioGR_001135
    • KBioSS_001494
    • 5-21-03-00508 (Beilstein Handbook Reference)
    • DivK1c_000841
    • SPBio_000130
    • SPBio_002014
    • BPBio1_000103
    • GTPL7171
    • SCHEMBL30702275
    • KBio1_000841
    • KBio2_001494
    • KBio2_004062
    • KBio2_006630
    • KBio3_001158
    • MSK2841
    • NINDS_000841
    • HMS3604L05
    • N,N-dimethyl-2-[(1-phenyl-1-pyridin-2-ylethyl)oxy]ethanamine
    • RFC84933
    • EBC-06825
    • MFCD00599469
    • STL018676
    • AKOS005657227
    • CCG-204443
    • DB00366
    • SDCCGSBI-0050336.P005
    • IDI1_000841
    • ( inverted exclamation markA)-Doxylamine
    • NCGC00021147-02
    • NCGC00021147-03
    • NCGC00021147-04
    • NCGC00021147-05
    • NCGC00021147-06
    • NCGC00021147-08
    • NCGC00021147-09
    • NCGC00021147-13
    • NCGC00021147-21
    • NCGC00089789-02
    • NCGC00089789-04
    • NCGC00089789-05
    • AC-15949
    • SBI-0050336.P004
    • DB-051407
    • AB00053466
    • NS00000474
    • D07878
    • EN300-123421
    • AB00053466-18
    • AB00053466_19
    • AB00053466_20
    • .alpha.-Dimethylaminoethoxyphenylmethyl-2-picoline
    • 469D216
    • L001076
    • Q423390
    • BRD-A44008656-036-05-0
    • BRD-A44008656-036-15-9
    • BRD-A44008656-036-24-1
    • BRD-A44008656-036-25-8
    • Z2242151271
    • N,N-dimethyl-2-[1-phenyl-1-(2-pyridyl)ethoxy]ethanamine
    • Phenyl-2-pyridylmethyl-.beta.-N,N-dimethylaminoethyl ether
    • N,N-Dimethyl-2-[1-phenyl-1-(2-pyridinyl)ethoxy]ethanamine #
    • 469-21-6

  • Applications

    Doxylamine (CAS 469-21-6) is used primarily in pharmaceuticals: as the active ingredient in over-the-counter sleep aids and in antihistamine formulations for allergy and cold symptom relief; it is also employed in prescription antiemetic regimens for nausea in pregnancy (often as doxylamine succinate in combination with pyridoxine).

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 583.73
    methanol 866.98
    isopropanol 216.79
    water 17.31
    ethyl acetate 277.44
    n-propanol 479.88
    acetone 243.51
    n-butanol 392.23
    acetonitrile 229.55
    DMF 427.43
    toluene 207.58
    isobutanol 364.37
    1,4-dioxane 462.31
    methyl acetate 262.24
    THF 310.04
    2-butanone 237.61
    n-pentanol 267.78
    sec-butanol 254.93
    n-hexane 25.81
    ethylene glycol 241.43
    NMP 375.8
    cyclohexane 100.9
    DMSO 502.9
    n-butyl acetate 201.04
    n-octanol 70.14
    chloroform 1948.76
    n-propyl acetate 177.53
    acetic acid 906.16
    dichloromethane 1830.19
    cyclohexanone 463.35
    propylene glycol 232.39
    isopropyl acetate 122.49
    DMAc 431.04
    2-ethoxyethanol 392.98
    isopentanol 269.48
    n-heptane 24.42
    ethyl formate 357.44
    1,2-dichloroethane 976.06
    n-hexanol 271.01
    2-methoxyethanol 609.15
    isobutyl acetate 123.16
    tetrachloromethane 227.09
    n-pentyl acetate 112.92
    transcutol 650.97
    n-heptanol 127.96
    ethylbenzene 90.92
    MIBK 97.83
    2-propoxyethanol 345.62
    tert-butanol 212.73
    MTBE 136.4
    2-butoxyethanol 225.62
    propionic acid 450.89
    o-xylene 132.51
    formic acid 540.27
    diethyl ether 211.28
    m-xylene 116.51
    p-xylene 124.45
    chlorobenzene 408.51
    dimethyl carbonate 115.26
    n-octane 9.45
    formamide 508.67
    cyclopentanone 335.9
    2-pentanone 161.51
    anisole 147.1
    cyclopentyl methyl ether 207.44
    gamma-butyrolactone 447.13
    1-methoxy-2-propanol 279.7
    pyridine 546.08
    3-pentanone 174.04
    furfural 571.8
    n-dodecane 6.58
    diethylene glycol 335.77
    diisopropyl ether 44.19
    tert-amyl alcohol 226.58
    acetylacetone 170.93
    n-hexadecane 7.4
    acetophenone 176.49
    methyl propionate 222.02
    isopentyl acetate 176.97
    trichloroethylene 1697.96
    n-nonanol 63.8
    cyclohexanol 377.54
    benzyl alcohol 243.98
    2-ethylhexanol 141.25
    isooctanol 100.11
    dipropyl ether 112.78
    1,2-dichlorobenzene 333.29
    ethyl lactate 126.18
    propylene carbonate 331.37
    n-methylformamide 360.7
    2-pentanol 171.74
    n-pentane 33.17
    1-propoxy-2-propanol 197.63
    1-methoxy-2-propyl acetate 164.9
    2-(2-methoxypropoxy) propanol 134.95
    mesitylene 65.77
    ε-caprolactone 392.86
    p-cymene 72.95
    epichlorohydrin 615.19
    1,1,1-trichloroethane 570.21
    2-aminoethanol 405.38
    morpholine-4-carbaldehyde 390.45
    sulfolane 474.94
    2,2,4-trimethylpentane 21.94
    2-methyltetrahydrofuran 274.25
    n-hexyl acetate 129.08
    isooctane 10.62
    2-(2-butoxyethoxy)ethanol 207.51
    sec-butyl acetate 105.16
    tert-butyl acetate 99.48
    decalin 30.95
    glycerin 343.4
    diglyme 395.42
    acrylic acid 462.17
    isopropyl myristate 47.44
    n-butyric acid 511.71
    acetyl acetate 198.89
    di(2-ethylhexyl) phthalate 82.85
    ethyl propionate 132.23
    nitromethane 682.04
    1,2-diethoxyethane 187.57
    benzonitrile 240.65
    trioctyl phosphate 52.36
    1-bromopropane 398.99
    gamma-valerolactone 484.1
    n-decanol 47.66
    triethyl phosphate 93.15
    4-methyl-2-pentanol 87.03
    propionitrile 241.19
    vinylene carbonate 401.92
    1,1,2-trichlorotrifluoroethane 699.78
    DMS 132.94
    cumene 68.98
    2-octanol 58.59
    2-hexanone 137.59
    octyl acetate 67.05
    limonene 104.43
    1,2-dimethoxyethane 371.27
    ethyl orthosilicate 93.1
    tributyl phosphate 65.98
    diacetone alcohol 134.35
    N,N-dimethylaniline 110.5
    acrylonitrile 303.7
    aniline 320.41
    1,3-propanediol 444.18
    bromobenzene 391.66
    dibromomethane 1131.27
    1,1,2,2-tetrachloroethane 1324.03
    2-methyl-cyclohexyl acetate 142.17
    tetrabutyl urea 78.09
    diisobutyl methanol 58.77
    2-phenylethanol 213.13
    styrene 118.55
    dioctyl adipate 90.62
    dimethyl sulfate 161.47
    ethyl butyrate 155.61
    methyl lactate 156.02
    butyl lactate 118.65
    diethyl carbonate 128.51
    propanediol butyl ether 151.02
    triethyl orthoformate 125.29
    p-tert-butyltoluene 60.9
    methyl 4-tert-butylbenzoate 130.59
    morpholine 543.73
    tert-butylamine 135.99
    n-dodecanol 38.68
    dimethoxymethane 231.9
    ethylene carbonate 334.44
    cyrene 172.55
    2-ethoxyethyl acetate 159.97
    2-ethylhexyl acetate 146.39
    1,2,4-trichlorobenzene 377.59
    4-methylpyridine 391.2
    dibutyl ether 73.94
    2,6-dimethyl-4-heptanol 58.77
    DEF 258.43
    dimethyl isosorbide 207.23
    tetrachloroethylene 967.74
    eugenol 146.0
    triacetin 142.08
    span 80 128.22
    1,4-butanediol 235.58
    1,1-dichloroethane 695.36
    2-methyl-1-pentanol 234.18
    methyl formate 339.01
    2-methyl-1-butanol 323.85
    n-decane 11.02
    butyronitrile 262.06
    3,7-dimethyl-1-octanol 68.09
    1-chlorooctane 53.42
    1-chlorotetradecane 21.55
    n-nonane 10.45
    undecane 8.05
    tert-butylcyclohexane 21.74
    cyclooctane 23.71
    cyclopentanol 253.91
    tetrahydropyran 444.27
    tert-amyl methyl ether 125.56
    2,5,8-trioxanonane 241.24
    1-hexene 92.6
    2-isopropoxyethanol 226.06
    2,2,2-trifluoroethanol 360.22
    methyl butyrate 201.65

    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