Doxepin

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  • Identifiers

    CAS number
    1668-19-5

    Molecular formula
    C19H21NO

    SMILES
    CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31

    Safety labels

    Acute Toxic
    Acute Toxic

    Health Hazard
    Health

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Floral 35.28%
    Animal 34.4%
    Sweet 33.83%
    Fruity 27.23%
    Fresh 25.98%
    Spicy 25.31%
    Citrus 22.53%
    Grape 21.51%
    Fishy 20.88%
    Grapefruit 20.46%

     

    Flavor
    Bitter 40.57%
    Herbal 34.15%
    Woody 20.89%
    Cedarleaf 19.99%
    Herb 19.79%
    Lovage 19.77%
    Fruity 19.62%
    Nitrile 19.5%
    Heather 19.41%
    Outdoor 19.33%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    4.3

    pKa est.
    7.47 (neutral)

    Molecular weight
    279.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 185-191 ºC
    • Crystals, melting point 184 to 186 °C, 188 to 189 °C (a cis-trans mixture of approx 1:5) /HYDROCHLORIDE/
    • Crystals, melting point 161 to 164 °C, 168 to 169 °C /MALEATE/
    • Melting point 192 to 193 °C /trans-HYDROCHLORIDE/
    • Crystals, melting point 209 to 210.5 °C /cis-HYDROCHLORIDE/

    Boiling point

    • 154-157 ºC at 0.03 mmHg
    • 154-157 °C @ 0.03 MM HG

    Flash point

    • 182.29 ˚C est.

    Solubility expt.

    • 31.6 mg/L (at 25 °C)
    • WHITE CRYSTALLINE SUBSTANCE; 1 G SOL IN 1 ML WATER, 2 ML ALCOHOL, 10 ML CHLOROFORM /HYDROCHLORIDE/
    • In water, 31.57 mg/l at 25 °C.

  • Synonyms

    • doxepin
    • Doxepine
    • 1668-19-5
    • (e)-doxepin
    • Doxepina
    • Doxepinum
    • Doxepinum [INN-Latin]
    • Doxepina [INN-Spanish]
    • trans-doxepin
    • MF 10
    • Doxepin, (E)-
    • CCRIS 9176
    • HSDB 3069
    • UNII-5ASJ6HUZ7D
    • Sinequan
    • 11-(3-(Dimethylamino)propylidene)-6H-dibenz(b,e)oxepine
    • Sinequan (TN)
    • 5ASJ6HUZ7D
    • 3607-34-9
    • 11-(3-Dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin
    • 11-(3-Dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin
    • N,N-Dimethyldibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine
    • (3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
    • 851NLB57HQ
    • Doxepin [USAN]
    • Doxepinum (INN-Latin)
    • Doxepina (INN-Spanish)
    • Dibenz(b,e)oxepin-delta(sup 11(6H)),gamma-propylamine, N,N-dimethyl-
    • 1-Propanamine, 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-
    • Deptran
    • 1-Propanamine, 3-dibenz[b,e]oxepin-11(6H)-ylidene-N,N-dimethyl-
    • (3e)-3-(Dibenzo[b,E]oxepin-11(6h)-Ylidene)-N,N-Dimethylpropan-1-Amine
    • Doxepin (INN)
    • [11C]doxepin
    • 3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine
    • [11C]-doxepin
    • Doxepin [INN:BAN]
    • NCGC00015344-03
    • CAS-1229-29-4
    • CHEBI:4710
    • DTXSID7022966
    • UNII-851NLB57HQ
    • NSC 108160
    • E-DOXEPIN
    • Tocris-0508
    • Prestwick2_000263
    • Prestwick3_000263
    • DOXEPIN, E-ISOMER
    • Lopac-D-4526
    • CHEMBL860
    • Doxepin [USAN:INN:BAN]
    • Lopac0_000339
    • BSPBio_000106
    • SCHEMBL116895
    • 3-dibenz(b,e)oxepin-11(6H)-ylidene-N,N-dimethyl-1-propanamine
    • BPBio1_000118
    • DTXCID202966
    • GTPL1225
    • GTPL3958
    • (E)-3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N,N-dimethylpropan-1-amine
    • 3-DIBENZO(B,E)OXEPIN-11(6H)-YLIDENE-N,N-DIMETHYLPROPAN-1-AMINE
    • HY-B0725A
    • D04AX01
    • DTXSID90859605
    • N06AA12
    • (3E)-3-DIBENZO(B,E)OXEPIN-11(6H)-YLIDENE-N,N-DIMETHYLPROPAN-1-AMINE
    • ODQWQRRAPPTVAG-GZTJUZNOSA-N
    • BDBM112780
    • Dibenz(b,e)oxepin-delta(11(6H),gamma)-propylamine, N,N-dimethyl-
    • CCG-204434
    • SDCCGSBI-0050327.P002
    • NCGC00015344-01
    • NCGC00015344-02
    • NCGC00015344-04
    • NCGC00015344-12
    • NCGC00015344-16
    • NCGC00024623-01
    • NCGC00162127-01
    • DA-52672
    • US8629135, SW-07
    • CS-0013584
    • NS00098752
    • C06971
    • D07875
    • L000699
    • BRD-K36616567-003-01-5
    • BRD-K54462405-003-03-3
    • BRD-K54462405-003-16-5
    • Q27077103
    • DOXEPIN IS A CIS-TRANS (APPROXIMATELY 1:5) MIXTURE
    • 11-(3-(DIMETHYLAMINO)PROPYLIDENE)-6H-DIBENZ(B,E)0XEPINE
    • 1-PROPANAMINE, 3-DIBENZ(B,E)OXEPIN-11(6H)-YLIDENE-N,N-DIMETHYL-, (3E)-
    • 5EH

  • Applications

    Doxepin, CAS 1668-19-5, is primarily used as an active pharmaceutical ingredient (API) in prescription medications within the class of tricyclic antidepressants. In the chemical industry it can serve as an intermediate or building block in the synthesis of related tricyclic amines for medicinal chemistry development. It is also used as a reference standard or analytical material in laboratories for method development and quality control. In medicinal chemistry research, it is commonly used as a model compound to study properties of tricyclic amine scaffolds.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 264.27
    methanol 310.33
    isopropanol 124.49
    water 1.33
    ethyl acetate 270.64
    n-propanol 248.0
    acetone 353.14
    n-butanol 228.97
    acetonitrile 209.68
    DMF 802.59
    toluene 180.38
    isobutanol 203.44
    1,4-dioxane 598.39
    methyl acetate 285.7
    THF 496.56
    2-butanone 303.19
    n-pentanol 212.64
    sec-butanol 146.98
    n-hexane 23.84
    ethylene glycol 154.3
    NMP 570.0
    cyclohexane 60.36
    DMSO 582.57
    n-butyl acetate 202.89
    n-octanol 66.17
    chloroform 1747.48
    n-propyl acetate 222.79
    acetic acid 481.59
    dichloromethane 1617.16
    cyclohexanone 428.43
    propylene glycol 143.1
    isopropyl acetate 147.54
    DMAc 657.51
    2-ethoxyethanol 434.16
    isopentanol 191.97
    n-heptane 21.14
    ethyl formate 315.51
    1,2-dichloroethane 937.45
    n-hexanol 179.27
    2-methoxyethanol 501.84
    isobutyl acetate 175.8
    tetrachloromethane 197.18
    n-pentyl acetate 148.45
    transcutol 755.86
    n-heptanol 105.83
    ethylbenzene 97.83
    MIBK 143.73
    2-propoxyethanol 358.21
    tert-butanol 128.75
    MTBE 136.13
    2-butoxyethanol 247.94
    propionic acid 266.73
    o-xylene 111.72
    formic acid 221.61
    diethyl ether 239.58
    m-xylene 99.78
    p-xylene 126.49
    chlorobenzene 365.05
    dimethyl carbonate 202.23
    n-octane 11.57
    formamide 303.11
    cyclopentanone 484.66
    2-pentanone 226.59
    anisole 214.06
    cyclopentyl methyl ether 239.81
    gamma-butyrolactone 559.03
    1-methoxy-2-propanol 259.6
    pyridine 574.07
    3-pentanone 231.31
    furfural 617.18
    n-dodecane 9.86
    diethylene glycol 354.92
    diisopropyl ether 62.89
    tert-amyl alcohol 126.3
    acetylacetone 254.38
    n-hexadecane 11.35
    acetophenone 216.97
    methyl propionate 266.2
    isopentyl acetate 186.26
    trichloroethylene 1634.98
    n-nonanol 67.62
    cyclohexanol 207.05
    benzyl alcohol 248.03
    2-ethylhexanol 117.81
    isooctanol 93.01
    dipropyl ether 127.8
    1,2-dichlorobenzene 326.59
    ethyl lactate 149.54
    propylene carbonate 353.51
    n-methylformamide 380.28
    2-pentanol 113.45
    n-pentane 24.85
    1-propoxy-2-propanol 193.76
    1-methoxy-2-propyl acetate 210.73
    2-(2-methoxypropoxy) propanol 175.69
    mesitylene 61.65
    ε-caprolactone 379.88
    p-cymene 67.65
    epichlorohydrin 836.33
    1,1,1-trichloroethane 613.17
    2-aminoethanol 216.86
    morpholine-4-carbaldehyde 622.4
    sulfolane 587.15
    2,2,4-trimethylpentane 17.63
    2-methyltetrahydrofuran 325.78
    n-hexyl acetate 162.57
    isooctane 11.91
    2-(2-butoxyethoxy)ethanol 256.24
    sec-butyl acetate 141.99
    tert-butyl acetate 132.4
    decalin 29.57
    glycerin 229.12
    diglyme 523.13
    acrylic acid 306.33
    isopropyl myristate 70.72
    n-butyric acid 328.23
    acetyl acetate 209.98
    di(2-ethylhexyl) phthalate 100.26
    ethyl propionate 167.35
    nitromethane 578.75
    1,2-diethoxyethane 266.84
    benzonitrile 267.51
    trioctyl phosphate 68.01
    1-bromopropane 369.61
    gamma-valerolactone 632.59
    n-decanol 55.98
    triethyl phosphate 111.96
    4-methyl-2-pentanol 78.2
    propionitrile 194.29
    vinylene carbonate 401.64
    1,1,2-trichlorotrifluoroethane 791.28
    DMS 201.25
    cumene 71.16
    2-octanol 56.94
    2-hexanone 194.73
    octyl acetate 96.12
    limonene 92.72
    1,2-dimethoxyethane 494.92
    ethyl orthosilicate 113.13
    tributyl phosphate 84.5
    diacetone alcohol 153.49
    N,N-dimethylaniline 137.51
    acrylonitrile 264.42
    aniline 276.04
    1,3-propanediol 257.18
    bromobenzene 378.89
    dibromomethane 928.91
    1,1,2,2-tetrachloroethane 1240.26
    2-methyl-cyclohexyl acetate 152.67
    tetrabutyl urea 101.1
    diisobutyl methanol 59.2
    2-phenylethanol 201.99
    styrene 146.57
    dioctyl adipate 124.05
    dimethyl sulfate 290.12
    ethyl butyrate 168.51
    methyl lactate 190.22
    butyl lactate 138.74
    diethyl carbonate 143.52
    propanediol butyl ether 166.86
    triethyl orthoformate 142.59
    p-tert-butyltoluene 59.36
    methyl 4-tert-butylbenzoate 153.97
    morpholine 619.53
    tert-butylamine 84.55
    n-dodecanol 46.96
    dimethoxymethane 394.9
    ethylene carbonate 332.64
    cyrene 219.33
    2-ethoxyethyl acetate 245.47
    2-ethylhexyl acetate 165.08
    1,2,4-trichlorobenzene 396.41
    4-methylpyridine 409.64
    dibutyl ether 91.21
    2,6-dimethyl-4-heptanol 59.2
    DEF 353.92
    dimethyl isosorbide 253.26
    tetrachloroethylene 840.54
    eugenol 183.64
    triacetin 189.62
    span 80 143.43
    1,4-butanediol 176.36
    1,1-dichloroethane 616.29
    2-methyl-1-pentanol 192.48
    methyl formate 359.66
    2-methyl-1-butanol 202.49
    n-decane 14.97
    butyronitrile 206.74
    3,7-dimethyl-1-octanol 71.68
    1-chlorooctane 64.38
    1-chlorotetradecane 31.01
    n-nonane 13.72
    undecane 11.66
    tert-butylcyclohexane 22.9
    cyclooctane 19.43
    cyclopentanol 184.79
    tetrahydropyran 423.21
    tert-amyl methyl ether 115.43
    2,5,8-trioxanonane 326.17
    1-hexene 92.02
    2-isopropoxyethanol 275.72
    2,2,2-trifluoroethanol 235.27
    methyl butyrate 236.28

    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