Bicuculline

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  • Identifiers

    CAS number
    485-49-4

    Molecular formula
    C20H17NO6

    SMILES
    CN1CCC2=CC3=C(C=C2[C@H]1[C@H]4C5=C(C6=C(C=C5)OCO6)C(=O)O4)OCO3

    Safety labels

    Acute Toxic
    Acute Toxic

    Environmental Hazard
    Environmental

  • Odor profile

    Fragrance
    Odorless 46.65%
    Sweet 28.78%
    Spicy 27.24%
    Vanilla 25.49%
    Phenolic 20.73%
    Powdery 20.01%
    Floral 20.01%
    Animal 19.97%
    Creamy 18.06%
    Coconut 17.87%

     

    Flavor
    Bitter 97.16%
    Bland 21.17%
    Sweet-like 18.26%
    Cedarleaf 18.02%
    Cereal 16.63%
    Parsley 16.6%
    Indole 16.41%
    Very strong 16.36%
    Lovage 16.35%
    Alkaline 16.16%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.6

    pKa est.
    5.02 (weak acid)

    Molecular weight
    367.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    892°C

    Flash point

    • 288.23 ˚C est.

  • Synonyms

    • bicuculline
    • 485-49-4
    • d-Bicuculline
    • Bicculine
    • Bicucullin
    • Y37615DVKC
    • (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[3,4-g][1,3]benzodioxol-8-one
    • DTXSID3042687
    • NSC-32192
    • CHEBI:3092
    • (6R)-6-[(5S)-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e][1,3]benzodioxol-8(6H)-one
    • Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,S*))-
    • (6R)-6-((5S)-6-methyl-5,6,7,8-tetrahydro(1,3)dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)(1,3)benzodioxol-8(6H)-one
    • (6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(3,4-g)(1,3)benzodioxol-8-one
    • (6R)-6-((5S)-6-methyl-7,8-dihydro-5H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-6H-furo(4,3-g)(1,3)benzodioxol-8-one
    • (6R)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6H-furo[4,3-g][1,3]benzodioxol-8-one
    • RefChem:119660
    • 6-(5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)furo(3,4-e)1,3-benzodioxol-8(6H)one
    • DTXCID1022687
    • (10R)-10-((5S)-6-methyl-2H,5H,6H,7H,8H-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3,5,11-trioxatricyclo(7.3.0.02,6)dodeca-1(9),2(6),7-trien-12-one
    • 207-619-7
    • (+)-Bicuculline
    • Bicuculline (+)
    • NSC32192
    • MFCD00005006
    • CHEMBL417990
    • (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-[1,3]dioxolo[4,5-e]isobenzofuran-8(6H)-one
    • (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]lisoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
    • NSC 32192
    • (6R)-6-((5S)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxolano[4,5-g]isoquinolin-5- yl))-6-hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one
    • Furo[3,4-e]-1,3-benzodioxol-8(6H)-one, 6-[(5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-, (6R)-
    • SR-01000075252
    • EINECS 207-619-7
    • BRN 0098786
    • UNII-Y37615DVKC
    • D-Bic uculline
    • bicuculline-(+)
    • IYGYMKDQCDOMRE-ZWKOTPCHSA-N
    • Bicuculline,(+)
    • Prestwick_96
    • Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-((5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (6R)-
    • (+)-Bicuculline?
    • Bicuculline (Standard)
    • BICUCULLINE [MI]
    • Prestwick0_000589
    • Prestwick1_000589
    • Prestwick2_000589
    • Prestwick3_000589
    • Biomol-NT_000252
    • (+)-Bicuculline, 98%
    • SCHEMBL8222
    • Lopac0_000234
    • BSPBio_000438
    • 4-27-00-06900 (Beilstein Handbook Reference)
    • MLS002153892
    • DivK1c_000609
    • SPBio_002657
    • BPBio1_000482
    • BPBio1_000794
    • GTPL2312
    • orb1304933
    • SCHEMBL29390611
    • SCHEMBL29652597
    • HMS501O11
    • HY-N0219R
    • KBio1_000609
    • NINDS_000609
    • GLXC-06284
    • HMS1569F20
    • HMS2096F20
    • HMS2235H18
    • HMS3266A07
    • HMS3414D19
    • HMS3652N20
    • HMS3678D19
    • HMS3886N09
    • HY-N0219
    • BDBM50000693
    • HB0896
    • PDSP2_000138
    • s7071
    • (+)-Bicuculline - Bio-X trade mark
    • AKOS024282673
    • CCG-204329
    • CS-5493
    • DB11562
    • EBC-615949
    • FB18590
    • IDI1_000609
    • NCGC00017385-06
    • (+)-Bicuculline, >=97.0% (TLC)
    • (6R)-6-[(5S)-5,6,7,8-Tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]furo[3,4-e]-1,3-benzodioxol-8(6H)-one
    • AC-31293
    • AS-17471
    • BB164251
    • SMR001233241
    • ST057559
    • ST057706
    • NS00031807
    • SW196408-2
    • B 9130
    • C09364
    • 485B494
    • Q3639734
    • SR-01000075252-1
    • SR-01000075252-4
    • SR-01000075252-5
    • WLN: T C566 DO FO KN EH&&TJ K1 J- ET B565 CVO JO LO EH KHJ
    • (10R)-10-[(5S)-6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3,5,11-trioxatricyclo[7.3.0.0,2,6]dodeca-1,6,8-trien-12-one
    • (6R)-6-((5S)-6-METHYL-5,6,7,8-TETRAHYDRO(1,3)DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)FURO(3,4-E)(1,3BENZODIOXOL-8(6H)-ONE
    • (6R)-6-[(5S)-6-Methyl-5,6,7,8-tetrahydro-2H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2H-furo[3,4-e][1,3]benzodioxol-8(6H)-one
    • (bicuculline) 6-Methyl-5-(8-oxo-6,8-dihydro-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-6-yl)-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-6-ium
    • (R)-6-((S)-6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one
    • (R)-6-((S)-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuro[5,4-d][1,3]dioxol-8(6H)-one
    • 6-((5S)-6-methyl-5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoquinolin-5-yl)-6 -hydro-2H-1,3-dioxoleno[4,5-e]isobenzofuran-8-one
    • 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one
    • 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one (Bicuculline)
    • 6-(6-Methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6H-furo[3'',4'':3,4]benzo[1,2-d][1,3]dioxol-8-one(bicuculline)
    • Furo[3,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [R-(R*,S*)]-
    • H0Z
    • 485-49-4

  • Applications

    Bicuculline (CAS 485-49-4) is primarily used as a pharmacological tool in neuroscience research to antagonize GABA-A receptors, enabling study of inhibitory synaptic transmission, receptor pharmacology, and network dynamics; it is employed in electrophysiology experiments on brain slices and cultured neurons to assess inhibitory signaling and ligand-receptor interactions; it is used in screening and characterization of CNS-active compounds that affect GABAergic pathways; it is applied in experimental models to investigate neuronal circuit function and synaptic dysregulation related to inhibition; and it is used in CNS drug discovery research under appropriate regulatory and safety conditions.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.99
    methanol 1.58
    isopropanol 1.12
    water 0.05
    ethyl acetate 12.7
    n-propanol 1.02
    acetone 12.25
    n-butanol 1.31
    acetonitrile 9.6
    DMF 24.11
    toluene 1.93
    isobutanol 1.03
    1,4-dioxane 12.0
    methyl acetate 12.66
    THF 15.39
    2-butanone 10.68
    n-pentanol 1.16
    sec-butanol 0.73
    n-hexane 0.03
    ethylene glycol 2.17
    NMP 24.45
    cyclohexane 0.11
    DMSO 29.15
    n-butyl acetate 10.29
    n-octanol 1.89
    chloroform 35.47
    n-propyl acetate 10.24
    acetic acid 26.1
    dichloromethane 31.74
    cyclohexanone 19.54
    propylene glycol 0.78
    isopropyl acetate 9.33
    DMAc 49.05
    2-ethoxyethanol 9.62
    isopentanol 2.19
    n-heptane 0.09
    ethyl formate 11.16
    1,2-dichloroethane 15.01
    n-hexanol 1.88
    2-methoxyethanol 14.24
    isobutyl acetate 7.67
    tetrachloromethane 3.15
    n-pentyl acetate 9.54
    transcutol 31.21
    n-heptanol 2.44
    ethylbenzene 0.96
    MIBK 6.97
    2-propoxyethanol 17.87
    tert-butanol 1.79
    MTBE 1.21
    2-butoxyethanol 13.35
    propionic acid 6.54
    o-xylene 1.55
    formic acid 16.25
    diethyl ether 1.83
    m-xylene 1.64
    p-xylene 1.79
    chlorobenzene 5.46
    dimethyl carbonate 17.17
    n-octane 0.07
    formamide 24.37
    cyclopentanone 21.67
    2-pentanone 8.79
    anisole 3.68
    cyclopentyl methyl ether 4.19
    gamma-butyrolactone 31.63
    1-methoxy-2-propanol 9.31
    pyridine 14.52
    3-pentanone 7.42
    furfural 38.46
    n-dodecane 0.12
    diethylene glycol 21.77
    diisopropyl ether 0.84
    tert-amyl alcohol 1.28
    acetylacetone 22.11
    n-hexadecane 0.15
    acetophenone 9.49
    methyl propionate 11.48
    isopentyl acetate 10.7
    trichloroethylene 51.43
    n-nonanol 2.44
    cyclohexanol 1.96
    benzyl alcohol 5.6
    2-ethylhexanol 2.14
    isooctanol 2.67
    dipropyl ether 2.21
    1,2-dichlorobenzene 7.23
    ethyl lactate 9.45
    propylene carbonate 19.72
    n-methylformamide 12.4
    2-pentanol 0.92
    n-pentane 0.03
    1-propoxy-2-propanol 10.92
    1-methoxy-2-propyl acetate 19.5
    2-(2-methoxypropoxy) propanol 15.53
    mesitylene 1.09
    ε-caprolactone 19.8
    p-cymene 1.75
    epichlorohydrin 34.43
    1,1,1-trichloroethane 12.15
    2-aminoethanol 1.86
    morpholine-4-carbaldehyde 36.04
    sulfolane 35.67
    2,2,4-trimethylpentane 0.05
    2-methyltetrahydrofuran 5.13
    n-hexyl acetate 8.44
    isooctane 0.05
    2-(2-butoxyethoxy)ethanol 17.14
    sec-butyl acetate 6.41
    tert-butyl acetate 8.21
    decalin 0.11
    glycerin 5.61
    diglyme 36.21
    acrylic acid 11.79
    isopropyl myristate 4.4
    n-butyric acid 11.31
    acetyl acetate 19.27
    di(2-ethylhexyl) phthalate 7.17
    ethyl propionate 9.24
    nitromethane 60.35
    1,2-diethoxyethane 8.9
    benzonitrile 11.39
    trioctyl phosphate 4.98
    1-bromopropane 2.48
    gamma-valerolactone 45.84
    n-decanol 1.88
    triethyl phosphate 8.27
    4-methyl-2-pentanol 1.34
    propionitrile 6.62
    vinylene carbonate 27.93
    1,1,2-trichlorotrifluoroethane 48.18
    DMS 13.71
    cumene 0.87
    2-octanol 1.39
    2-hexanone 7.44
    octyl acetate 5.67
    limonene 1.73
    1,2-dimethoxyethane 19.76
    ethyl orthosilicate 6.38
    tributyl phosphate 5.92
    diacetone alcohol 11.83
    N,N-dimethylaniline 2.85
    acrylonitrile 15.69
    aniline 4.64
    1,3-propanediol 4.96
    bromobenzene 5.26
    dibromomethane 12.18
    1,1,2,2-tetrachloroethane 30.8
    2-methyl-cyclohexyl acetate 9.26
    tetrabutyl urea 8.81
    diisobutyl methanol 1.6
    2-phenylethanol 8.49
    styrene 1.17
    dioctyl adipate 8.21
    dimethyl sulfate 27.64
    ethyl butyrate 9.26
    methyl lactate 11.88
    butyl lactate 10.01
    diethyl carbonate 9.64
    propanediol butyl ether 7.26
    triethyl orthoformate 8.26
    p-tert-butyltoluene 1.45
    methyl 4-tert-butylbenzoate 13.15
    morpholine 10.52
    tert-butylamine 0.59
    n-dodecanol 1.48
    dimethoxymethane 16.88
    ethylene carbonate 22.6
    cyrene 17.16
    2-ethoxyethyl acetate 17.06
    2-ethylhexyl acetate 8.29
    1,2,4-trichlorobenzene 10.36
    4-methylpyridine 11.27
    dibutyl ether 2.3
    2,6-dimethyl-4-heptanol 1.6
    DEF 14.05
    dimethyl isosorbide 27.81
    tetrachloroethylene 20.72
    eugenol 14.37
    triacetin 15.77
    span 80 9.49
    1,4-butanediol 2.21
    1,1-dichloroethane 9.21
    2-methyl-1-pentanol 1.76
    methyl formate 14.31
    2-methyl-1-butanol 1.38
    n-decane 0.17
    butyronitrile 4.98
    3,7-dimethyl-1-octanol 2.64
    1-chlorooctane 1.03
    1-chlorotetradecane 0.57
    n-nonane 0.11
    undecane 0.14
    tert-butylcyclohexane 0.08
    cyclooctane 0.06
    cyclopentanol 2.02
    tetrahydropyran 4.09
    tert-amyl methyl ether 1.3
    2,5,8-trioxanonane 26.99
    1-hexene 0.18
    2-isopropoxyethanol 7.46
    2,2,2-trifluoroethanol 20.91
    methyl butyrate 11.43

    Scent© AI

1 4

IFRA standard 51

Recommendation
No restriction
Maximum acceptable concentrations in the finished product (%)
Category 1
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Category 3
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Category 4
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Category 5B
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Household care products with mostly hand contact, including aerosol/spray products (with potential leave-on skin contact)
 No restriction
Category 5C
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Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate without UV exposure
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Category 5D
Baby Creams, baby Oils and baby talc
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Products with intended skin contact but minimal transfer of fragrance to skin from inert substrate with potential UV exposure
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Category 6
Products with oral and lip exposure
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Products not intended for direct skin contact, minimal or insignificant transfer to skin
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