Ezogabine

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  • Identifiers

    CAS number
    150812-12-7

    Molecular formula
    C16H18FN3O2

    SMILES
    CCOC(=O)NC1=C(C=C(C=C1)NCC2=CC=C(C=C2)F)N

    Safety labels

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Grape 51.21%
    Fruity 39.03%
    Odorless 37.39%
    Meaty 31.74%
    Savory 28.37%
    Citrus 27.18%
    Cooked 27.09%
    Animal 26.02%
    Cheesy 25.01%
    Ripe 22.28%

     

    Flavor
    Fruity 52.22%
    Bitter 46.7%
    Mild 39.1%
    Odorless 36.73%
    Grape 29.24%
    Floral 24.17%
    Sweet 22.98%
    Orange blossom 22.12%
    Orange flower 21.96%
    Petitgrain 20.72%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.8

    pKa est.
    6.3 (neutral)

    Molecular weight
    303.33 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    519°C

    Melting point expt.

    • 138-145 °C

    Flash point

    • 232.71 ˚C est.

    Solubility expt.

    • At room temperature ... practically insoluble in aqueous media above pH4, while the solubility is higher in polar organic solvents

  • Synonyms

    • Retigabine
    • 150812-12-7
    • Ezogabine
    • Potiga
    • Trobalt
    • D-23129
    • Ezogabine [USAN]
    • Potiva
    • GKE-841
    • N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester
    • Retigabine [INN]
    • Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate
    • WAY-143841
    • D 20443
    • ethyl N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamate
    • UNII-12G01I6BBU
    • AWD21-360
    • GW582892X
    • Retigabine (INN)
    • Ezogabine (USAN)
    • GW 582892X
    • GW-582892X
    • WAY 143841
    • Potiga (TN)
    • CHEBI:68584
    • HSDB 8171
    • GKI 841
    • EZOGABINE [MI]
    • AWD-21360
    • EZOGABINE [VANDF]
    • Ethyl (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)carbamate
    • RETIGABINE [MART.]
    • N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamic acid ethyl ester
    • RETIGABINE [WHO-DD]
    • Retigabine (1.0 mg/mL in Acetonitrile)
    • CHEMBL41355
    • RETIGABINE [EMA EPAR]
    • 12G01I6BBU
    • ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate
    • EZOGABINE [ORANGE BOOK]
    • Retigabine-d4 Dihydrochloride
    • DTXSID40164615
    • Ethyl [2-amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]carbamate
    • N03AX21
    • Carbamic acid, (2-amino-4-(((4-fluorophenyl)methyl)amino)phenyl)-, ethyl ester
    • ethyl (2-amino-4-((4-fluorobenzyl)amino)phenyl)carbamate
    • 2-AMINO-4-(4-FLUORBENZYLAMINO)-1-ETHOXYCARBONYLAMINOBENZENE
    • ethyl N-[2-azanyl-4-[(4-fluorophenyl)methylamino]phenyl]carbamate
    • RETIGABINE (MART.)
    • [2-Amino-4-(4-fluoro-benzylamino)-phenyl]-carbamic acid ethyl ester
    • CARBAMIC ACID, (2-AMINO-4-(((4-FLUORO-PHENYL)METHYL)AMINO)PHENYL)-ETHYL ESTER
    • RTG
    • D 23129
    • 1285886-70-5
    • retigabinum
    • Retigabina
    • Retigabin
    • Retigabine?
    • n-(2-amino-4-(4-fluorobenzylamino)-phenyl)carbamic acid ethyl ester
    • n-[2-amino-4-(4-fluorobenzylamino)-phenyl]carbamic acid ethyl ester
    • ethyl N-(2-amino-4-(4-fluorobenzylamino)phenyl)carbamate hydrochloride
    • FBX
    • ADD-230001
    • KE-0201
    • SCHEMBL20835
    • Retigabine, analytical standard
    • GTPL2601
    • XEN496
    • DEA No. 2779
    • DTXCID5087106
    • Retigabine, >=98% (HPLC)
    • XEN-496
    • PCOBBVZJEWWZFR-UHFFFAOYSA-N
    • [2-Amino-4-[[(4-fluorophenyl)methyl]amino]phenyl]-carbamate
    • HMS3748I09
    • HMS3885L20
    • BCP04194
    • EX-A2203
    • KBC88670
    • N-(2-amino-4-[fluorobenzylamino]-phenyl) carbamic acid|D-23129
    • Retigabine,D2312, D-23129
    • BDBM50143558
    • MFCD04307735
    • s4733
    • ZINC00016154
    • AKOS015895311
    • AC-6908
    • CCG-267503
    • CS-0990
    • DB04953
    • FA61501
    • NCGC00346739-01
    • NCGC00346739-05
    • NCGC00346739-06
    • AW21-360
    • HY-15471
    • BCP0726000089
    • AE3 - Newer Anti-epileptic drug mixtures 3
    • NS00040686
    • D09569
    • A809076
    • Q2146170
    • BRD-K89917372-001-01-2
    • ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate
    • N-(2-amino-4-(4-fluorobenzylamino)-phenyl)carbamic acid ethylester
    • N-[2-amino-4-[(4-fluorophenyl)methylamino]phenyl]carbamic acid ethyl ester

  • Applications

    Ezogabine (CAS 150812-12-7) is a compound primarily used in neuroscience and medicinal chemistry research to study KV7 (KCNQ) potassium channel modulation and neuronal excitability; in pharmaceutical R&D it serves as a tool compound and scaffold for developing ion-channel modulators and for structure-activity relationship (SAR) analyses, as well as for evaluating mechanism and pharmacology in relevant biological systems.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 31.56
    methanol 43.24
    isopropanol 17.76
    water 0.07
    ethyl acetate 20.94
    n-propanol 23.68
    acetone 66.47
    n-butanol 18.28
    acetonitrile 15.03
    DMF 49.36
    toluene 2.04
    isobutanol 9.31
    1,4-dioxane 50.7
    methyl acetate 23.79
    THF 218.58
    2-butanone 49.71
    n-pentanol 12.9
    sec-butanol 14.64
    n-hexane 0.07
    ethylene glycol 4.53
    NMP 16.63
    cyclohexane 0.1
    DMSO 283.69
    n-butyl acetate 5.82
    n-octanol 2.38
    chloroform 19.53
    n-propyl acetate 7.7
    acetic acid 57.66
    dichloromethane 16.77
    cyclohexanone 33.78
    propylene glycol 11.95
    isopropyl acetate 7.99
    DMAc 152.22
    2-ethoxyethanol 67.0
    isopentanol 11.67
    n-heptane 0.08
    ethyl formate 19.44
    1,2-dichloroethane 12.13
    n-hexanol 6.49
    2-methoxyethanol 113.98
    isobutyl acetate 3.66
    tetrachloromethane 1.08
    n-pentyl acetate 3.65
    transcutol 86.88
    n-heptanol 4.08
    ethylbenzene 1.1
    MIBK 8.35
    2-propoxyethanol 35.67
    tert-butanol 16.22
    MTBE 5.41
    2-butoxyethanol 20.41
    propionic acid 16.18
    o-xylene 1.38
    formic acid 36.43
    diethyl ether 6.17
    m-xylene 1.07
    p-xylene 1.63
    chlorobenzene 2.87
    dimethyl carbonate 11.18
    n-octane 0.05
    formamide 66.69
    cyclopentanone 51.44
    2-pentanone 23.01
    anisole 7.83
    cyclopentyl methyl ether 8.15
    gamma-butyrolactone 43.31
    1-methoxy-2-propanol 53.01
    pyridine 27.54
    3-pentanone 13.58
    furfural 44.08
    n-dodecane 0.07
    diethylene glycol 35.22
    diisopropyl ether 0.69
    tert-amyl alcohol 11.5
    acetylacetone 33.04
    n-hexadecane 0.08
    acetophenone 9.68
    methyl propionate 16.26
    isopentyl acetate 6.22
    trichloroethylene 29.51
    n-nonanol 2.84
    cyclohexanol 7.82
    benzyl alcohol 12.07
    2-ethylhexanol 2.93
    isooctanol 3.14
    dipropyl ether 2.83
    1,2-dichlorobenzene 2.88
    ethyl lactate 9.02
    propylene carbonate 15.41
    n-methylformamide 31.88
    2-pentanol 5.99
    n-pentane 0.06
    1-propoxy-2-propanol 17.84
    1-methoxy-2-propyl acetate 13.28
    2-(2-methoxypropoxy) propanol 21.13
    mesitylene 0.55
    ε-caprolactone 22.91
    p-cymene 0.94
    epichlorohydrin 71.25
    1,1,1-trichloroethane 5.82
    2-aminoethanol 17.89
    morpholine-4-carbaldehyde 42.04
    sulfolane 49.34
    2,2,4-trimethylpentane 0.08
    2-methyltetrahydrofuran 28.03
    n-hexyl acetate 4.84
    isooctane 0.04
    2-(2-butoxyethoxy)ethanol 29.96
    sec-butyl acetate 4.39
    tert-butyl acetate 7.62
    decalin 0.1
    glycerin 23.47
    diglyme 60.07
    acrylic acid 16.2
    isopropyl myristate 2.39
    n-butyric acid 26.74
    acetyl acetate 11.83
    di(2-ethylhexyl) phthalate 4.69
    ethyl propionate 7.29
    nitromethane 110.99
    1,2-diethoxyethane 13.38
    benzonitrile 7.13
    trioctyl phosphate 2.64
    1-bromopropane 3.5
    gamma-valerolactone 81.87
    n-decanol 2.2
    triethyl phosphate 4.87
    4-methyl-2-pentanol 3.21
    propionitrile 10.09
    vinylene carbonate 13.64
    1,1,2-trichlorotrifluoroethane 53.85
    DMS 6.31
    cumene 0.78
    2-octanol 1.79
    2-hexanone 12.49
    octyl acetate 3.27
    limonene 1.09
    1,2-dimethoxyethane 81.13
    ethyl orthosilicate 4.62
    tributyl phosphate 3.45
    diacetone alcohol 20.6
    N,N-dimethylaniline 4.4
    acrylonitrile 14.5
    aniline 9.11
    1,3-propanediol 39.07
    bromobenzene 1.98
    dibromomethane 7.05
    1,1,2,2-tetrachloroethane 25.97
    2-methyl-cyclohexyl acetate 5.75
    tetrabutyl urea 5.8
    diisobutyl methanol 1.8
    2-phenylethanol 9.29
    styrene 1.4
    dioctyl adipate 5.44
    dimethyl sulfate 18.34
    ethyl butyrate 6.36
    methyl lactate 16.69
    butyl lactate 7.0
    diethyl carbonate 5.4
    propanediol butyl ether 14.53
    triethyl orthoformate 6.05
    p-tert-butyltoluene 0.84
    methyl 4-tert-butylbenzoate 10.22
    morpholine 72.37
    tert-butylamine 3.47
    n-dodecanol 1.63
    dimethoxymethane 56.48
    ethylene carbonate 11.51
    cyrene 19.12
    2-ethoxyethyl acetate 10.5
    2-ethylhexyl acetate 3.87
    1,2,4-trichlorobenzene 4.57
    4-methylpyridine 16.73
    dibutyl ether 2.77
    2,6-dimethyl-4-heptanol 1.8
    DEF 19.56
    dimethyl isosorbide 27.13
    tetrachloroethylene 12.19
    eugenol 13.78
    triacetin 8.78
    span 80 12.56
    1,4-butanediol 13.16
    1,1-dichloroethane 7.66
    2-methyl-1-pentanol 9.7
    methyl formate 24.83
    2-methyl-1-butanol 10.36
    n-decane 0.11
    butyronitrile 11.24
    3,7-dimethyl-1-octanol 2.78
    1-chlorooctane 0.69
    1-chlorotetradecane 0.34
    n-nonane 0.08
    undecane 0.09
    tert-butylcyclohexane 0.09
    cyclooctane 0.04
    cyclopentanol 11.67
    tetrahydropyran 23.58
    tert-amyl methyl ether 4.38
    2,5,8-trioxanonane 42.59
    1-hexene 0.63
    2-isopropoxyethanol 26.61
    2,2,2-trifluoroethanol 15.68
    methyl butyrate 11.48

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
Products applied to the lips
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Rinse-off products applied to the hair with some hand contact
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Category 2
Products applied to the axillae
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Leave-on products applied to the hair with some hand contact
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Category 3
Products applied to the face/body using fingertips
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Products with significant anogenital exposure
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Category 4
Products related to fine fragrance
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Products with body and hand exposure, primarily rinse off
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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
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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
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