Norethindrone

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  • Identifiers

    CAS number
    68-22-4

    Molecular formula
    C20H26O2

    SMILES
    C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Woody 74.05%
    Spicy 37.55%
    Cedar 37.41%
    Amber 37.23%
    Dry 35.05%
    Fresh 30.25%
    Earthy 29.53%
    Balsamic 28.81%
    Camphoreous 27.75%
    Herbal 26.91%

     

    Flavor
    Bitter 73.12%
    Cedarleaf 21.84%
    Alkaline 20.67%
    Lovage 20.18%
    Ripe apricot 20.0%
    Sweet-like 19.84%
    Cereal 19.79%
    Shrimp 19.78%
    Beet 19.77%
    Soil 19.71%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.0

    pKa est.
    8.3 (weak base)

    Molecular weight
    298.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderate

    Boiling point est.
    381°C

    Melting point expt.

    • 202-208C
    • 204 °C
    • Crystals from methylene chloride and hexane; max absorption: 240 nm (e = 18,690); MP: 161-162 °C /Norethindrone acetate/
    • 203.5 °C
    • 397.4 °F

    Flash point

    • 184.55 ˚C est.

    Solubility expt.

    • PRACTICALLY INSOL IN WATER; SOL IN CHLOROFORM, ETHER, DIOXANE; SOL @ 25 °C: 1 IN 12.5 PARTS 95% ETHANOL, 1 IN 4 PARTS ACETONE /ACETATE/
    • Solubility in double-distilled water, 0.98 mg/L /Norethindrone acetate/
    • SLIGHTLY SOL IN VEGETABLE OIL; SOL @ 25 °C: 1 IN 150 PARTS 95% ETHANOL, 1 IN 5 PARTS PYRIDINE, 1 IN 80 PARTS ACETONE, 1 IN 30 PARTS CHLOROFORM
    • Sparingly soluble in alcohol; soluble in chloroform and dioxane; slightly soluble in ether.
    • In double-distilled water, 1.44 mg/L
    • In water, 7.04 mg/L water at 25 °C
    • 6.68e-03 g/L

  • Synonyms

    • norethindrone
    • Norethisterone
    • 68-22-4
    • Norethisteron
    • Micronor
    • 19-Norethisterone
    • Norlutin
    • Anovule
    • Camila
    • Gestest
    • Noriday
    • Utovlan
    • Primolut-N
    • Micronovum
    • Norethynodrone
    • Conludag
    • Norcolut
    • Norluten
    • Triella
    • Mini-pill
    • Noresthisterone
    • Norethisteronum
    • Norethyndron
    • Noretisterona
    • Conludaf
    • Micronett
    • Mini-Pe
    • Noralutin
    • Norgestin
    • Norluton
    • Proluteasi
    • Norfor
    • Utovlar
    • Norpregneninlone
    • Norpregneninolone
    • 19-Nor-ethindrone
    • Nor-QD
    • Ethinylnortestosterone
    • Norethynodron
    • Anovulatorio
    • Ciclovulan
    • Estrinor
    • Microneth
    • Norethadrone
    • Synphase
    • Genora
    • Nelova
    • Nodiol
    • Milli
    • Noraethisteronum
    • Norpregneninotone
    • Ethynylnortestosterone
    • 17alpha-Ethynyl-19-nortestosterone
    • Synphasic 28
    • Brevinor 21
    • Brevinor 28
    • Trinovum 21
    • Errin
    • Menzol
    • Noriday 28
    • 19-Nor-17alpha-ethynyltestosterone
    • Jenest-28
    • Ethynylmortestosterone
    • Brevinor-1 21
    • Brevinor-1 28
    • Ovysmen 1 35
    • Ortho-Novum 1 35
    • Ortho-Novum 1 50
    • Anhydrohydroxynorprogesterone
    • Noretisterone
    • Ortho-Novum 7 7 7
    • Ovysmen 0.5 35
    • Ortho 1 35
    • 19-Norethinyltestosterone
    • Ortho 7 7 7
    • 17alpha-Ethinyl-19-nortestosterone
    • Primolut N
    • Minovlar
    • 17alpha-Ethynyl-4-estren-17-ol-3-one
    • 19-Nor-17-ethinyltestosterone
    • 17-alpha-Ethynyl-19-nortestosterone
    • 19-Nor-17-alpha-ethynyltestosterone
    • Ethinyl-19-nortestosterone
    • Normapause
    • 17alpha-Ethinylestra-4-en-17beta-ol-3-one
    • Norethisteronum [INN-Latin]
    • Noretisterona [INN-Spanish]
    • NSC-9564
    • 17-Hydroxy-19-nor-17alpha-pregn-4-en-20-yn-3-one
    • 17beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
    • 17-alpha-Ethynyl-4-estren-17-ol-3-one
    • 19-Norethindrone
    • 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
    • 17alpha-Ethynyl-17-hydroxy-4-estren-3-one
    • 19-Nor-17alpa-ethynyltestosterone
    • Norethindrone (USP)
    • 19-nor-17alpha-Ethynylandrosten-17beta-ol-3-one
    • CCRIS 484
    • 4-Estren-17alpha-ethynyl-17beta-ol-3-one
    • 17alpha-Ethynyl-19-norandrost-4-en-17beta-ol-3-one
    • Activella
    • N.E.E.
    • 17-alpha-Ethynyl-17-hydroxy-4-estren-3-one
    • SC 4640
    • HSDB 3370
    • 17alpha-Ethynyl-17beta-hydroxy-19-norandrost-4-en-3-one
    • 17-beta-Hydroxy-19-norpregn-4-en-20-yn-3-one
    • 19-Nortestosterone, 17-ethynyl-
    • Nor-Q.D.
    • 17-ethynyl-17beta-hydroxyestr-4-en-3-one
    • 19-Nor-17-alpha-ethynylandrosten-17-beta-ol-3-one
    • EINECS 200-681-6
    • 17-alpha-Ethynyl-19-norandrost-4-en-17-beta-ol-3-one
    • 17-Hydroxy-19-nor-17-alpha-pregn-4-en-20-yn-3-one
    • UNII-T18F433X4S
    • 19-Nor-17-alpha-ethynyl-17-beta-hydroxy-4-androsten-3-one
    • BRN 1915671
    • CHEBI:7627
    • Norethindrone [USP]
    • DTXSID9023380
    • Norethisterone [INN]
    • AI3-26422
    • 17alpha-Ethynyl-19-nor-4-androsten-17beta-ol-3-one
    • T18F433X4S
    • (17-alpha)-17-Hydroxy-19-norpregn-4-en-20-yn-3-one
    • Norethindrone (Standard)
    • 17-alpha-Ethinylestra-4-en-17-beta-ol-3-one
    • Gencept

  • Applications

    Norethindrone (CAS 68-22-4) is a synthetic progestin used primarily as an active pharmaceutical ingredient in hormonal contraception (both combined oral contraceptives and progestin-only formulations) and in hormone replacement therapy formulations for women. It is also involved in the research and development of progestin drugs and can serve as a lead scaffold or starting material for the synthesis of related progestins; its handling and manufacture follow pharmaceutical regulations and standard production practices.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 41.1
    methanol 96.22
    isopropanol 30.56
    water 0.64
    ethyl acetate 90.68
    n-propanol 39.4
    acetone 87.3
    n-butanol 34.66
    acetonitrile 44.18
    DMF 285.44
    toluene 80.86
    isobutanol 22.31
    1,4-dioxane 184.53
    methyl acetate 57.14
    THF 396.06
    2-butanone 64.63
    n-pentanol 15.5
    sec-butanol 10.89
    n-hexane 0.91
    ethylene glycol 23.43
    NMP 72.3
    cyclohexane 3.66
    DMSO 141.73
    n-butyl acetate 51.18
    n-octanol 10.59
    chloroform 203.13
    n-propyl acetate 46.86
    acetic acid 55.13
    dichloromethane 139.83
    cyclohexanone 121.85
    propylene glycol 15.98
    isopropyl acetate 103.08
    DMAc 125.36
    2-ethoxyethanol 62.67
    isopentanol 30.54
    n-heptane 1.4
    ethyl formate 48.41
    1,2-dichloroethane 84.37
    n-hexanol 27.24
    2-methoxyethanol 158.44
    isobutyl acetate 38.86
    tetrachloromethane 23.1
    n-pentyl acetate 39.01
    transcutol 286.47
    n-heptanol 18.93
    ethylbenzene 22.89
    MIBK 73.43
    2-propoxyethanol 113.75
    tert-butanol 28.39
    MTBE 14.82
    2-butoxyethanol 64.19
    propionic acid 37.11
    o-xylene 31.59
    formic acid 45.65
    diethyl ether 41.69
    m-xylene 50.34
    p-xylene 26.0
    chlorobenzene 74.36
    dimethyl carbonate 93.34
    n-octane 0.76
    formamide 84.94
    cyclopentanone 170.98
    2-pentanone 81.2
    anisole 72.91
    cyclopentyl methyl ether 78.26
    gamma-butyrolactone 172.31
    1-methoxy-2-propanol 134.18
    pyridine 138.81
    3-pentanone 59.3
    furfural 169.86
    n-dodecane 0.77
    diethylene glycol 119.67
    diisopropyl ether 16.1
    tert-amyl alcohol 10.0
    acetylacetone 196.81
    n-hexadecane 0.94
    acetophenone 69.26
    methyl propionate 79.07
    isopentyl acetate 54.91
    trichloroethylene 191.87
    n-nonanol 13.17
    cyclohexanol 27.02
    benzyl alcohol 51.27
    2-ethylhexanol 17.02
    isooctanol 17.02
    dipropyl ether 25.96
    1,2-dichlorobenzene 71.12
    ethyl lactate 39.84
    propylene carbonate 92.03
    n-methylformamide 113.45
    2-pentanol 17.41
    n-pentane 1.44
    1-propoxy-2-propanol 69.22
    1-methoxy-2-propyl acetate 122.96
    2-(2-methoxypropoxy) propanol 63.25
    mesitylene 29.16
    ε-caprolactone 92.22
    p-cymene 15.98
    epichlorohydrin 215.51
    1,1,1-trichloroethane 69.22
    2-aminoethanol 37.91
    morpholine-4-carbaldehyde 174.09
    sulfolane 153.11
    2,2,4-trimethylpentane 0.87
    2-methyltetrahydrofuran 62.92
    n-hexyl acetate 41.55
    isooctane 1.46
    2-(2-butoxyethoxy)ethanol 89.02
    sec-butyl acetate 41.61
    tert-butyl acetate 97.53
    decalin 2.4
    glycerin 50.39
    diglyme 197.67
    acrylic acid 45.15
    isopropyl myristate 21.42
    n-butyric acid 73.56
    acetyl acetate 109.36
    di(2-ethylhexyl) phthalate 28.85
    ethyl propionate 54.83
    nitromethane 148.74
    1,2-diethoxyethane 67.86
    benzonitrile 73.91
    trioctyl phosphate 19.61
    1-bromopropane 28.21
    gamma-valerolactone 253.21
    n-decanol 9.87
    triethyl phosphate 31.95
    4-methyl-2-pentanol 19.47
    propionitrile 60.21
    vinylene carbonate 117.27
    1,1,2-trichlorotrifluoroethane 127.71
    DMS 76.89
    cumene 15.42
    2-octanol 9.67
    2-hexanone 35.65
    octyl acetate 24.49
    limonene 16.09
    1,2-dimethoxyethane 135.37
    ethyl orthosilicate 28.73
    tributyl phosphate 22.7
    diacetone alcohol 84.36
    N,N-dimethylaniline 39.61
    acrylonitrile 92.83
    aniline 74.13
    1,3-propanediol 64.22
    bromobenzene 77.15
    dibromomethane 71.84
    1,1,2,2-tetrachloroethane 134.92
    2-methyl-cyclohexyl acetate 40.97
    tetrabutyl urea 30.72
    diisobutyl methanol 14.85
    2-phenylethanol 59.21
    styrene 30.15
    dioctyl adipate 35.97
    dimethyl sulfate 118.81
    ethyl butyrate 49.71
    methyl lactate 69.95
    butyl lactate 43.15
    diethyl carbonate 41.8
    propanediol butyl ether 50.01
    triethyl orthoformate 40.98
    p-tert-butyltoluene 14.97
    methyl 4-tert-butylbenzoate 69.24
    morpholine 155.85
    tert-butylamine 13.76
    n-dodecanol 7.41
    dimethoxymethane 266.44
    ethylene carbonate 99.58
    cyrene 70.9
    2-ethoxyethyl acetate 85.11
    2-ethylhexyl acetate 38.42
    1,2,4-trichlorobenzene 76.81
    4-methylpyridine 111.68
    dibutyl ether 14.74
    2,6-dimethyl-4-heptanol 14.85
    DEF 75.36
    dimethyl isosorbide 121.03
    tetrachloroethylene 92.16
    eugenol 70.17
    triacetin 79.6
    span 80 47.43
    1,4-butanediol 17.78
    1,1-dichloroethane 65.45
    2-methyl-1-pentanol 14.37
    methyl formate 89.97
    2-methyl-1-butanol 17.53
    n-decane 1.27
    butyronitrile 48.83
    3,7-dimethyl-1-octanol 14.67
    1-chlorooctane 6.62
    1-chlorotetradecane 3.24
    n-nonane 0.97
    undecane 0.96
    tert-butylcyclohexane 2.01
    cyclooctane 1.61
    cyclopentanol 26.86
    tetrahydropyran 92.11
    tert-amyl methyl ether 11.96
    2,5,8-trioxanonane 123.49
    1-hexene 4.67
    2-isopropoxyethanol 42.35
    2,2,2-trifluoroethanol 41.42
    methyl butyrate 57.61

    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