Tetrodotoxin

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  • Identifiers

    CAS number
    4368-28-9

    Molecular formula
    C11H17N3O8

    SMILES
    C([C@@]1([C@H]2[C@@H]3[C@H](N=C(N[C@@]34[C@@H]([C@@H]1O[C@]([C@H]4O)(O2)O)O)N)O)O)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 78.27%
    Sweet 31.22%
    Savory 20.65%
    Cooling 18.01%
    Fishy 15.7%
    Meaty 15.61%
    Bitter 14.64%
    Milky 14.06%
    Smoky 13.41%
    Burnt 12.99%

     

    Flavor
    Bitter 61.68%
    Odorless 44.43%
    Sweet 40.65%
    Sweet-like 29.42%
    Fatty 23.61%
    Bland 22.51%
    Alkaline 20.77%
    Cauliflower 20.42%
    Very slight 20.11%
    Bouillon 19.66%

     

    Odor impact est.
    Odorless

  • Properties

    XLogP3-AA
    -5.9

    pKa est.
    8.09 (weak base)

    Molecular weight
    319.27 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Boiling point est.
    2523°C

    Melting point expt.

    • 225 °C (decomposes)

    Flash point

    • 273.75 ˚C est.

    Solubility expt.

    • Soluble in dilute acetic acid; slightly soluble in dry alcohol, ether; practically insoluble in other organic solvents

  • Synonyms

    • TETRODOTOXIN
    • Tarichatoxin
    • Spheroidine
    • Tetrodotoxine
    • Tetrodoxin
    • Babylonia japonica toxin 1
    • Maculotoxin
    • 4368-28-9
    • Tectin
    • BJT 1
    • Pft-1 toxin
    • Tetrodontoxin
    • tetrodotoxina
    • Fugu poison
    • 3KUM2721U9
    • (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d) pyrimidine-4,7,10,11,12-pentol
    • Octahydro-12-(hydroxymethyl)-2-imino-5,9:7,10a-dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol
    • DTXSID10881342
    • Tetradotoxin
    • Toxin, Fugu
    • 5,9:7,10A-DIMETHANO-10AH-(1,3)DIOXOCINO(6,5-D)PYRIMIDINE-4,7,10,11,12-PENTOL, 2-AMINO-1,4,4A,5,9,10-HEXAHYDRO-12-(HYDROXYMETHYL)-, (4R,4AR,5R,7S,9S,10S,10AR,11S,12S)-
    • 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-
    • CHEBI:9506
    • tetrodotoxinum
    • (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-ene-5,9,12,13,14-pentol
    • (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.17,11.01,6]tetradec-3-ene-5,9,12,13,14-pentol
    • RefChem:6297
    • DTXCID101022591
    • (11S,13S)-3-amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-en-4-ium-9-olate
    • (13S)-3-amino-5,12,13,14-tetrahydroxy-14-(hydroxymethyl)-8,10-dioxa-2-aza-4-azoniatetracyclo(7.3.1.17,11.01,6)tetradec-3-en-9-olate
    • (1R,5R,6R,7R,9S,11S,12R,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo(7.3.1.17,11.01,6)tetradec-3-ene-5,9,12,13,14-pentol
    • 224-458-8
    • Fugu Toxin
    • CHEMBL507974
    • TTX
    • (1R,5R,6R,7R,9S,11S,12S,13S,14S)-3-amino-14-(hydroxymethyl)-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1~7,11~.0~1,6~]tetradec-3-ene-5,9,12,13,14-pentol (non-preferred name)
    • tettrodotoxin
    • UNII-3KUM2721U9
    • CCRIS 9328
    • HSDB 3543
    • 9SR
    • EINECS 224-458-8
    • BRN 0049176
    • TETRODOTOXIN [MI]
    • TETRODOTOXIN [INN]
    • Tetrodotoxin - citrate free
    • 4-27-00-08206 (Beilstein Handbook Reference)
    • TETRODOTOXIN [WHO-DD]
    • SCHEMBL6406675
    • SCHEMBL29352502
    • MSK9101
    • CFMYXEVWODSLAX-QOZOJKKESA-N
    • BDBM50344821
    • FT29063
    • 5,9:7,10a-Dimethano-10ah-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R-(4alpha,4aalpha,5alpha,7alpha,9alpha,10alpha,10abeta,11S*,12S*))-
    • 10-hydroxymethyl-5-imino-(2S)-12,13-dioxa-4,6-diazatetracyclo[7.3.1.13,11.03,8]tetradecane-1,2,7,10,14-pentaol
    • 10-hydroxymethyl-5-imino-(2S)-12,13-dioxa-4,6-diazatetracyclo[7.3.1.13,11.03,8]tetradecane-1,2,7,10,14-pentaolCitrate
    • 5,9:7,10a-Dimethano-10aH-(1,3)dioxocino(6,5-d)pyrimidine-4,7,10,11,12-pentol, octahydro-12-(hydroxymethyl)-2-imino-, (4R,4aR,5R,7S,9S,10S,10aR,11S,12S)-
    • 4368-28-9

  • Applications

    Tetrodotoxin (CAS 4368-28-9) is primarily used in biomedical and neuroscience research as a highly selective blocker of voltage-gated sodium channels (Nav), enabling study of action potential generation and sodium-channel function in neurons and brain tissue; it is commonly used as a pharmacological tool and reference toxin in electrophysiology experiments and toxin-detection assays; in some pharmaceutical R&D contexts, it may be evaluated as a probe to understand pain signaling mechanisms, but therapeutic use is not established and subject to strict regulation; overall, it serves as a laboratory toxin and research reagent with applications limited to controlled settings.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 0.44
    methanol 2.19
    isopropanol 0.11
    water 7.63
    ethyl acetate 0.09
    n-propanol 0.14
    acetone 0.11
    n-butanol 0.09
    acetonitrile 0.07
    DMF 4.78
    toluene 0.04
    isobutanol 0.04
    1,4-dioxane 0.45
    methyl acetate 0.07
    THF 0.75
    2-butanone 0.08
    n-pentanol 0.05
    sec-butanol 0.05
    n-hexane 0.01
    ethylene glycol 2.88
    NMP 8.49
    cyclohexane 0.03
    DMSO 18.35
    n-butyl acetate 0.12
    n-octanol 0.06
    chloroform 0.02
    n-propyl acetate 0.06
    acetic acid 1.16
    dichloromethane 0.05
    cyclohexanone 0.31
    propylene glycol 0.7
    isopropyl acetate 0.05
    DMAc 2.96
    2-ethoxyethanol 1.14
    isopentanol 0.04
    n-heptane 0.04
    ethyl formate 0.19
    1,2-dichloroethane 0.05
    n-hexanol 0.12
    2-methoxyethanol 4.99
    isobutyl acetate 0.02
    tetrachloromethane 0.03
    n-pentyl acetate 0.08
    transcutol 0.73
    n-heptanol 0.14
    ethylbenzene 0.02
    MIBK 0.05
    2-propoxyethanol 1.81
    tert-butanol 0.06
    MTBE 0.01
    2-butoxyethanol 0.9
    propionic acid 0.2
    o-xylene 0.05
    formic acid 25.41
    diethyl ether 0.08
    m-xylene 0.04
    p-xylene 0.03
    chlorobenzene 0.01
    dimethyl carbonate 0.48
    n-octane 0.02
    formamide 16.44
    cyclopentanone 0.59
    2-pentanone 0.09
    anisole 0.04
    cyclopentyl methyl ether 0.25
    gamma-butyrolactone 1.1
    1-methoxy-2-propanol 1.81
    pyridine 0.29
    3-pentanone 0.09
    furfural 1.98
    n-dodecane 0.01
    diethylene glycol 5.54
    diisopropyl ether 0.02
    tert-amyl alcohol 0.03
    acetylacetone 0.23
    n-hexadecane 0.01
    acetophenone 0.1
    methyl propionate 0.22
    isopentyl acetate 0.07
    trichloroethylene 0.07
    n-nonanol 0.06
    cyclohexanol 0.1
    benzyl alcohol 0.09
    2-ethylhexanol 0.06
    isooctanol 0.06
    dipropyl ether 0.18
    1,2-dichlorobenzene 0.02
    ethyl lactate 0.26
    propylene carbonate 0.34
    n-methylformamide 2.68
    2-pentanol 0.04
    n-pentane 0.01
    1-propoxy-2-propanol 0.8
    1-methoxy-2-propyl acetate 0.4
    2-(2-methoxypropoxy) propanol 0.34
    mesitylene 0.03
    ε-caprolactone 0.34
    p-cymene 0.04
    epichlorohydrin 0.4
    1,1,1-trichloroethane 0.01
    2-aminoethanol 1.32
    morpholine-4-carbaldehyde 5.61
    sulfolane 5.28
    2,2,4-trimethylpentane 0.0
    2-methyltetrahydrofuran 0.16
    n-hexyl acetate 0.06
    isooctane 0.0
    2-(2-butoxyethoxy)ethanol 0.56
    sec-butyl acetate 0.03
    tert-butyl acetate 0.06
    decalin 0.01
    glycerin 6.64
    diglyme 1.51
    acrylic acid 0.5
    isopropyl myristate 0.02
    n-butyric acid 0.2
    acetyl acetate 0.08
    di(2-ethylhexyl) phthalate 0.04
    ethyl propionate 0.08
    nitromethane 1.54
    1,2-diethoxyethane 0.14
    benzonitrile 0.05
    trioctyl phosphate 0.05
    1-bromopropane 0.02
    gamma-valerolactone 2.3
    n-decanol 0.04
    triethyl phosphate 0.12
    4-methyl-2-pentanol 0.02
    propionitrile 0.05
    vinylene carbonate 0.37
    1,1,2-trichlorotrifluoroethane 2.28
    DMS 0.12
    cumene 0.02
    2-octanol 0.05
    2-hexanone 0.05
    octyl acetate 0.04
    limonene 0.06
    1,2-dimethoxyethane 1.02
    ethyl orthosilicate 0.09
    tributyl phosphate 0.04
    diacetone alcohol 0.3
    N,N-dimethylaniline 0.07
    acrylonitrile 0.13
    aniline 0.09
    1,3-propanediol 1.28
    bromobenzene 0.01
    dibromomethane 0.02
    1,1,2,2-tetrachloroethane 0.06
    2-methyl-cyclohexyl acetate 0.07
    tetrabutyl urea 0.12
    diisobutyl methanol 0.04
    2-phenylethanol 0.15
    styrene 0.02
    dioctyl adipate 0.04
    dimethyl sulfate 1.93
    ethyl butyrate 0.12
    methyl lactate 1.19
    butyl lactate 0.21
    diethyl carbonate 0.08
    propanediol butyl ether 0.5
    triethyl orthoformate 0.14
    p-tert-butyltoluene 0.04
    methyl 4-tert-butylbenzoate 0.22
    morpholine 0.73
    tert-butylamine 0.02
    n-dodecanol 0.03
    dimethoxymethane 1.94
    ethylene carbonate 0.24
    cyrene 0.95
    2-ethoxyethyl acetate 0.15
    2-ethylhexyl acetate 0.06
    1,2,4-trichlorobenzene 0.03
    4-methylpyridine 0.14
    dibutyl ether 0.04
    2,6-dimethyl-4-heptanol 0.04
    DEF 0.57
    dimethyl isosorbide 0.98
    tetrachloroethylene 0.13
    eugenol 0.29
    triacetin 0.11
    span 80 0.26
    1,4-butanediol 0.32
    1,1-dichloroethane 0.01
    2-methyl-1-pentanol 0.02
    methyl formate 1.67
    2-methyl-1-butanol 0.04
    n-decane 0.01
    butyronitrile 0.04
    3,7-dimethyl-1-octanol 0.03
    1-chlorooctane 0.02
    1-chlorotetradecane 0.01
    n-nonane 0.01
    undecane 0.01
    tert-butylcyclohexane 0.0
    cyclooctane 0.02
    cyclopentanol 0.17
    tetrahydropyran 0.13
    tert-amyl methyl ether 0.03
    2,5,8-trioxanonane 1.02
    1-hexene 0.02
    2-isopropoxyethanol 0.31
    2,2,2-trifluoroethanol 1.77
    methyl butyrate 0.11

    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