Methenamine

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  • Identifiers

    CAS number
    100-97-0

    Molecular formula
    C6H12N4

    SMILES
    C1N2CN3CN1CN(C2)C3

    Safety labels

    Flammable
    Flammable

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fishy 51.32%
    Odorless 34.6%
    Animal 31.73%
    Sweet 19.84%
    Cheesy 15.11%
    Ripe 15.06%
    Nutty 14.88%
    Earthy 14.86%
    Musty 12.98%
    Oily 12.52%

     

    Flavor
    Bitter 79.77%
    Alkaline 16.19%
    Cereal 15.4%
    Sweet-like 15.34%
    Rotten 14.96%
    Shrimp 14.62%
    Cedarleaf 14.61%
    Very strong 14.39%
    Indole 14.29%
    Nitrile 14.23%

     

    Odor impact est.
    High

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    7.07 (neutral)

    Molecular weight
    140.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • 536 °F (sublimes) (NTP, 1992)
    • Sublimes at about 260 °C without melting and with partial decomposition
    • Sour taste; mp: 127-130 °C; ph of soln 4 /Methenamine mandelate/
    • Odorless, crystalline powder; melting point: ~190 °C with decomposition; soluble in 8 parts water; slight soluble in alcohol /Methenamine sulfosalicylate/
    • > 250 °C

    Boiling point

    • Sublimes (NTP, 1992)

    Flash point

    • 124.06 ˚C est.
    • 482 °F (NTP, 1992)
    • 482 °F
    • 250 °C (482 °F) - closed cup
    • 250 °C c.c.

    Solubility expt.

    • >21 [ug/mL] (The mean of the results at pH 7.4)
    • greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
    • In water, 302,300 mg/L at 25 °C
    • Solubility of methenamine in 100 g of various solvents at 20 °C is: 13.4 g chloroform, 7.25 g in methanol, 2.89 g in absolute ethanol, 0.65 g in acetone, 0.23 g in benzene, 0.14 g in xylene, 0.06 g in ether, and near zero in petroleum ether.
    • At 12 °C, 81.3 g dissolves in 100 g of water; the solubility decreases slightly with increasing temperature.
    • Freely soluble in water; practically insoluble in petroleum ether
    • For more Solubility (Complete) data for METHENAMINE (6 total), please visit the HSDB record page.
    • 449 mg/mL at 12 °C
    • Solubility in water: good

  • Synonyms

    • methenamine
    • Hexamethylenetetramine
    • 100-97-0
    • Hexamine
    • Urotropine
    • Aminoform
    • Hexamethylenamine
    • Urotropin
    • 1,3,5,7-Tetraazaadamantane
    • HMTA
    • Hexamethylene tetramine
    • Methenamin
    • Uritone
    • Formamine
    • Hexamethylenetetraamine
    • Aminoformaldehyde
    • Ammoform
    • Ammonioformaldehyde
    • Antihydral
    • Cystamin
    • Cystogen
    • Duirexol
    • Hexaform
    • Metenamina
    • Metramine
    • Resotropin
    • Uratrine
    • Urodeine
    • Xametrin
    • Formin
    • Heterin
    • Uramin
    • Preparation AF
    • Hexamethyleneamine
    • Hexilmethylenamine
    • Hexa-Flo-Pulver
    • Ekagom H
    • methenaminum
    • Hexaloids
    • Hexaminum
    • Aceto HMT
    • Herax UTS
    • Hexasan
    • Hexamethylentetramin
    • Nocceler H
    • Sanceler H
    • Formin (heterocycle)
    • Hexamine (heterocycle)
    • Vulkacit H 30
    • Hexamethylentetraminum
    • Hexamethylentetramine
    • S 4 (heterocycle)
    • Hexamethylenetetraminum
    • 1,3,5,7-Tetraazatricyclo[3.3.1.13,7]decane
    • Esametilentetramina
    • Hexasan (VAN)
    • Metenamine
    • Methamin
    • Caswell No. 482
    • Uro-phosphate
    • 1,3,5,7-tetraazatricyclo[3.3.1.1~3,7~]decane
    • Sanceler HT
    • Heksa K
    • Hexamine Superfine
    • Nocceler H-PO
    • Sanceler HT-PO
    • Hexa (vulcanization accelerator)
    • Hexa B
    • Cohedur H 30
    • Rhenogran HEXA 80
    • Thixon 715B
    • 1,3,5,7-Tetraazatricyclo (3.3.1.1(3,7))decane
    • CCRIS 2297
    • HSDB 563
    • Vesaloin
    • Urisol
    • DTXSID6020692
    • HMT
    • Metenamina [INN-Spanish]
    • Methenaminum [INN-Latin]
    • UNII-J50OIX95QV
    • EINECS 202-905-8
    • J50OIX95QV
    • NSC 26346
    • NSC-26346
    • Hexamine (JAN)
    • Hexamine (TN)
    • EL 10 (corrosion inhibitor)
    • EPA Pesticide Chemical Code 045501
    • NSC 403347
    • CHEBI:6824
    • INS NO.239
    • 1,3,5,7-Tetraazatricyclo(3.3.1.13,7)decane
    • AI3-09611
    • Hexamethylenetetramine (aliphatic)
    • INS-239
    • 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 37))decane
    • EL 10
    • Silver Methenamine
    • Methenamine (USP/INN)
    • Methenamine [USP:INN]
    • 1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
    • NSC-403347
    • DTXCID00692
    • H.M.T.
    • E-239
    • EC 202-905-8
    • Formin (the heterocyclic compound)
    • NSC26346
    • MFCD00006895
    • 1,3,5,7-Tetraazatricyclo(3.3.1.1(sup 3,7))decane
    • NCGC00094719-04
    • E239
    • HEXAMINE [JAN]
    • Hexamine Silver
    • Methenamine (USP:INN)
    • Metenamina (INN-Spanish)
    • Methenaminum (INN-Latin)
    • Methenamine Silver
    • METHENAMINE (MART.)
    • METHENAMINE [MART.]
    • METHENAMINE (USP-RS)
    • METHENAMINE [USP-RS]
    • S 4
    • 1,3,5,7-Tetraazatricyclo[3.3.1.1(3,7)]decane
    • 1,3,5,7-tetraazatricyclo[3.3.1.1^{3,7}]decane
    • METHENAMINE (EP MONOGRAPH)
    • METHENAMINE [EP MONOGRAPH]

  • Applications

    Methenamine (CAS 100-97-0) is primarily used as a urinary antiseptic in pharmaceuticals, leveraging its acid-triggered release of formaldehyde to inhibit microbial growth in urine. It also serves as an organic synthesis intermediate for nitrogen-containing compounds and heterocycles, and acts as a formaldehyde donor in resin and coating chemistries under acidic conditions for curing or crosslinking. Additionally, it is used as a precursor for certain aminated polymers and as a general laboratory/research reagent.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 32.45
    methanol 75.32
    isopropanol 17.97
    water 596.39
    ethyl acetate 38.32
    n-propanol 22.33
    acetone 30.7
    n-butanol 16.97
    acetonitrile 58.92
    DMF 80.09
    toluene 8.71
    isobutanol 15.79
    1,4-dioxane 34.58
    methyl acetate 52.55
    THF 42.19
    2-butanone 23.31
    n-pentanol 9.51
    sec-butanol 13.64
    n-hexane 0.91
    ethylene glycol 81.14
    NMP 150.68
    cyclohexane 2.23
    DMSO 68.05
    n-butyl acetate 26.55
    n-octanol 8.07
    chloroform 137.02
    n-propyl acetate 17.61
    acetic acid 603.53
    dichloromethane 107.57
    cyclohexanone 36.5
    propylene glycol 38.84
    isopropyl acetate 16.09
    DMAc 82.86
    2-ethoxyethanol 38.84
    isopentanol 10.84
    n-heptane 2.42
    ethyl formate 66.46
    1,2-dichloroethane 38.07
    n-hexanol 14.81
    2-methoxyethanol 89.46
    isobutyl acetate 10.61
    tetrachloromethane 40.77
    n-pentyl acetate 14.97
    transcutol 58.78
    n-heptanol 10.92
    ethylbenzene 3.3
    MIBK 7.16
    2-propoxyethanol 55.6
    tert-butanol 14.27
    MTBE 6.97
    2-butoxyethanol 33.73
    propionic acid 115.99
    o-xylene 8.45
    formic acid 700.9
    diethyl ether 9.96
    m-xylene 6.97
    p-xylene 5.6
    chlorobenzene 28.31
    dimethyl carbonate 33.18
    n-octane 1.11
    formamide 402.09
    cyclopentanone 52.16
    2-pentanone 14.6
    anisole 9.13
    cyclopentyl methyl ether 17.02
    gamma-butyrolactone 150.6
    1-methoxy-2-propanol 43.39
    pyridine 52.42
    3-pentanone 15.15
    furfural 208.39
    n-dodecane 0.87
    diethylene glycol 80.16
    diisopropyl ether 3.05
    tert-amyl alcohol 13.17
    acetylacetone 26.77
    n-hexadecane 0.95
    acetophenone 18.78
    methyl propionate 38.99
    isopentyl acetate 18.4
    trichloroethylene 133.56
    n-nonanol 7.56
    cyclohexanol 17.35
    benzyl alcohol 19.98
    2-ethylhexanol 9.92
    isooctanol 8.16
    dipropyl ether 10.05
    1,2-dichlorobenzene 35.11
    ethyl lactate 25.2
    propylene carbonate 98.55
    n-methylformamide 122.17
    2-pentanol 8.92
    n-pentane 1.6
    1-propoxy-2-propanol 37.27
    1-methoxy-2-propyl acetate 33.51
    2-(2-methoxypropoxy) propanol 25.66
    mesitylene 4.39
    ε-caprolactone 59.3
    p-cymene 7.28
    epichlorohydrin 82.09
    1,1,1-trichloroethane 47.63
    2-aminoethanol 64.64
    morpholine-4-carbaldehyde 119.17
    sulfolane 130.17
    2,2,4-trimethylpentane 1.2
    2-methyltetrahydrofuran 29.62
    n-hexyl acetate 14.96
    isooctane 0.66
    2-(2-butoxyethoxy)ethanol 29.79
    sec-butyl acetate 9.11
    tert-butyl acetate 11.37
    decalin 1.13
    glycerin 98.03
    diglyme 52.02
    acrylic acid 199.36
    isopropyl myristate 5.36
    n-butyric acid 88.87
    acetyl acetate 50.41
    di(2-ethylhexyl) phthalate 12.98
    ethyl propionate 15.87
    nitromethane 388.56
    1,2-diethoxyethane 14.09
    benzonitrile 34.28
    trioctyl phosphate 8.61
    1-bromopropane 13.29
    gamma-valerolactone 105.26
    n-decanol 5.55
    triethyl phosphate 17.02
    4-methyl-2-pentanol 5.2
    propionitrile 27.72
    vinylene carbonate 126.33
    1,1,2-trichlorotrifluoroethane 191.99
    DMS 27.07
    cumene 3.31
    2-octanol 5.81
    2-hexanone 9.19
    octyl acetate 8.67
    limonene 8.45
    1,2-dimethoxyethane 29.06
    ethyl orthosilicate 14.77
    tributyl phosphate 11.13
    diacetone alcohol 20.18
    N,N-dimethylaniline 8.18
    acrylonitrile 58.69
    aniline 28.17
    1,3-propanediol 58.01
    bromobenzene 22.44
    dibromomethane 54.41
    1,1,2,2-tetrachloroethane 84.31
    2-methyl-cyclohexyl acetate 15.38
    tetrabutyl urea 11.99
    diisobutyl methanol 6.12
    2-phenylethanol 25.39
    styrene 4.29
    dioctyl adipate 10.0
    dimethyl sulfate 58.83
    ethyl butyrate 19.83
    methyl lactate 52.04
    butyl lactate 22.29
    diethyl carbonate 18.43
    propanediol butyl ether 26.14
    triethyl orthoformate 18.15
    p-tert-butyltoluene 7.04
    methyl 4-tert-butylbenzoate 23.55
    morpholine 45.53
    tert-butylamine 7.79
    n-dodecanol 4.24
    dimethoxymethane 31.41
    ethylene carbonate 78.43
    cyrene 39.44
    2-ethoxyethyl acetate 26.81
    2-ethylhexyl acetate 15.97
    1,2,4-trichlorobenzene 50.43
    4-methylpyridine 36.54
    dibutyl ether 5.46
    2,6-dimethyl-4-heptanol 6.12
    DEF 31.45
    dimethyl isosorbide 45.14
    tetrachloroethylene 84.64
    eugenol 28.63
    triacetin 29.13
    span 80 23.2
    1,4-butanediol 24.61
    1,1-dichloroethane 34.89
    2-methyl-1-pentanol 7.1
    methyl formate 119.46
    2-methyl-1-butanol 12.83
    n-decane 1.33
    butyronitrile 23.09
    3,7-dimethyl-1-octanol 6.95
    1-chlorooctane 4.36
    1-chlorotetradecane 2.04
    n-nonane 1.22
    undecane 1.04
    tert-butylcyclohexane 1.05
    cyclooctane 1.15
    cyclopentanol 29.11
    tetrahydropyran 17.48
    tert-amyl methyl ether 7.59
    2,5,8-trioxanonane 39.04
    1-hexene 2.24
    2-isopropoxyethanol 22.37
    2,2,2-trifluoroethanol 439.15
    methyl butyrate 20.94

    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