Pyrilamine Maleate

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  • Identifiers

    CAS number
    59-33-6

    Molecular formula
    C21H27N3O5

    SMILES
    CN(C)CCN(CC1=CC=C(C=C1)OC)C2=CC=CC=N2.C(=C\C(=O)O)\C(=O)O

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Fishy 36.93%
    Animal 34.17%
    Sweet 28.29%
    Roasted 27.48%
    Odorless 25.78%
    Cheesy 25.4%
    Savory 24.51%
    Cooling 23.18%
    Meaty 22.7%
    Ripe 22.52%

     

    Flavor
    Bitter 42.75%
    Mild 26.11%
    Odorless 21.99%
    Bland 21.84%
    Green pepper 20.55%
    Syrup 20.55%
    Carrot 20.21%
    Cedarleaf 20.07%
    Tomato leaf 20.06%
    Herbal 19.66%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    6.58 (neutral)

    Molecular weight
    401.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    452°C

    Melting point expt.

    • 212 to 214 °F (NTP, 1992)

    Flash point

    • 184.84 ˚C est.

    Solubility expt.

    • greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
    • >60.2 [ug/mL] (The mean of the results at pH 7.4)

  • Synonyms

    • PYRILAMINE MALEATE
    • Mepyramine maleate
    • 59-33-6
    • Anisopyradamine
    • Histatex
    • Histan
    • Minihist
    • Diaminide maleate
    • Paraminyl maleate
    • Antihist
    • Pyraninyl
    • Renstamin
    • Enrumay
    • Paramal
    • Pymafed
    • Stangen maleate
    • Anthisan maleate
    • Statomin maleate
    • Thylogen maleate
    • Neoantergan maleate
    • Pyranilamine maleate
    • Pyranisamine maleate
    • Pyra maleate
    • Neo-Antergan maleate
    • Prefrin A
    • 2786 R.P. maleate
    • Neo-antergan
    • Mepyramine hydrogen maleinate
    • Histavet-P
    • NSC-3604
    • R35D29L3ZA
    • DTXSID4021216
    • N-Dimethylaminoethyl-N-p-methoxy-alpha-aminopyridine maleate
    • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-, (Z)-2-butenedioate (1:1)
    • DTXCID201216
    • Pyridine, 2-((2-(dimethylamino)ethyl)(p-methoxybenzyl)amino)-, maleate (1:1)
    • 1,2-Ethanediamine, N-((4-methoxyphenyl)methyl)-N',N'-dimethyl-N-2-pyridinyl-, (2Z)-2-butenedioate (1:1)
    • HistALL
    • Maleate, Mepyramine
    • Maleate, Pyrilamine
    • Childrens PediaClear 8
    • RefChem:55949
    • Pyrilamine Maleate Injection
    • 200-422-7
    • Pyrilamine maleate salt
    • Histosol
    • Histine
    • Pyramal maleate
    • Pyra-Maleate
    • MFCD00069333
    • 2-((2-(Dimethylamino)ethyl)(p-methoxybenzyl)amino)pyridine maleate (1:1)
    • N1-(4-methoxybenzyl)-N2,N2-dimethyl-N1-(pyridin-2-yl)ethane-1,2-diamine maleate
    • MLS000069668
    • Kriptin maleate
    • Dorantamin maleate
    • SMR000058495
    • Histavet-P (veterinary)
    • (E)-But-2-enedioic acid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
    • (Z)-but-2-enedioic acid;N'-[(4-methoxyphenyl)methyl]-N,N-dimethyl-N'-pyridin-2-ylethane-1,2-diamine
    • Pyma
    • 1,2-Ethanediamine,N-[(4-methoxyphenyl)methyl]-N',N'-dimethyl-N-2-pyridinyl-,(2Z)-2-butenedioate (1:1)
    • Mepiramine maleate
    • component of Pyrdex
    • N1-[(4-Methoxyphenyl)methyl]-N2,N2-dimethyl-N1-2-pyridinyl-1,2-ethanediamine (2Z)-2-Butenedioate
    • Pymafed (TN)
    • CCRIS 1330
    • CAS-59-33-6
    • SR-01000000225
    • NSC 3604
    • EINECS 200-422-7
    • Pyrilamine maleate (USP)
    • component of Endotussin-NN
    • UNII-R35D29L3ZA
    • Pyrilamine maleate [USAN:USP]
    • N,N-Dimethyl-N'-(4-methoxybenzyl)-N'-(2-pyridyl)ethylenediamine maleate
    • N-p-Methoxybenzyl-N',N'-dimethyl-N-alpha-pyridylethylenediamine maleate
    • Prestwick_634
    • Mepyramine maleate CRS
    • Opera_ID_1702
    • 2-[[2-(Dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine bimaleate
    • P 5514
    • SCHEMBL27430
    • SCHEMBL97901
    • MLS001148634
    • N,N-dimethyl-N'-{[4-(methyloxy)phenyl]methyl}-N'-pyridin-2-ylethane-1,2-diamine (2Z)-but-2-enedioate
    • Mepyramine maleate (Standard)
    • Pyrilamine maleate; Mepyramine
    • SPECTRUM1500519
    • orb1309293
    • PYRILAMINE MALEATE [MI]
    • CHEMBL1201006
    • HMS500I17
    • HY-B1281R
    • MSK14309X
    • NSC3604
    • GLXC-15567
    • HMS1568J20
    • HMS1920N10
    • HMS2092E11
    • HMS2095J20
    • HMS2234I23
    • HMS2234I24
    • HMS3262B22
    • HMS3411M20
    • HMS3675M20
    • HMS3712J20
    • HMS5083K17
    • Pharmakon1600-01500519
    • PYRILAMINE MALEATE [VANDF]
    • MEPYRAMINE MALEATE [MART.]
    • HY-B1281
    • MEPYRAMINE MALEATE [WHO-DD]
    • PYRILAMINE MALEATE [USP-RS]
    • Tox21_200514
    • Tox21_500890
    • 2-[[2-(Dimethylamino)ethyl](p-methoxybenzyl)amino]pyridine maleate
    • CCG-39244
    • EBC-74038
    • HB2622
    • N-(Dimethylamino)ethyl-N-(p-methoxy)-.alpha.-aminopyridine maleate
    • NSC757305
    • s4382
    • AKOS015950805
    • N-(p-Methoxybenzyl)-N',N'-dimethyl-N-.alpha.-pyridylethylenediamine maleate
    • FP27345
    • LP00890
    • NSC-757305
    • 59-33-6

  • Applications

    Pyrilamine Maleate (CAS 59-33-6) is encountered in pharmaceutical contexts as an active pharmaceutical ingredient in antihistamine formulations for allergy relief (commonly in oral tablets or syrups) and as the pyrilamine maleate salt to improve aqueous solubility and formulation handling. In chemical manufacturing and medicinal chemistry, the compound serves as a versatile intermediate for the synthesis of other heterocyclic amines and related pharmaceutical molecules. It is used in pharmacology and toxicology research as a reference compound or reagent, and in analytical settings as a standard for method development and quality control of antihistamine products. Depending on formulation goals, the salt form can influence stability and bioavailability, with uses subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 339.85
    methanol 438.71
    isopropanol 110.08
    water 12.63
    ethyl acetate 247.83
    n-propanol 240.96
    acetone 139.48
    n-butanol 177.32
    acetonitrile 159.01
    DMF 196.54
    toluene 78.87
    isobutanol 151.16
    1,4-dioxane 237.23
    methyl acetate 205.31
    THF 181.21
    2-butanone 150.32
    n-pentanol 122.68
    sec-butanol 127.09
    n-hexane 3.5
    ethylene glycol 193.64
    NMP 107.25
    cyclohexane 12.14
    DMSO 461.9
    n-butyl acetate 67.9
    n-octanol 16.11
    chloroform 1068.85
    n-propyl acetate 91.31
    acetic acid 746.09
    dichloromethane 1153.38
    cyclohexanone 180.59
    propylene glycol 206.71
    isopropyl acetate 80.93
    DMAc 323.72
    2-ethoxyethanol 383.2
    isopentanol 107.32
    n-heptane 3.97
    ethyl formate 231.61
    1,2-dichloroethane 515.36
    n-hexanol 73.95
    2-methoxyethanol 568.57
    isobutyl acetate 55.01
    tetrachloromethane 95.42
    n-pentyl acetate 29.1
    transcutol 506.38
    n-heptanol 29.03
    ethylbenzene 23.69
    MIBK 48.02
    2-propoxyethanol 214.02
    tert-butanol 98.18
    MTBE 63.75
    2-butoxyethanol 103.05
    propionic acid 295.78
    o-xylene 48.57
    formic acid 555.73
    diethyl ether 89.92
    m-xylene 47.14
    p-xylene 34.45
    chlorobenzene 132.5
    dimethyl carbonate 84.23
    n-octane 1.63
    formamide 558.08
    cyclopentanone 156.16
    2-pentanone 88.7
    anisole 63.0
    cyclopentyl methyl ether 91.49
    gamma-butyrolactone 241.47
    1-methoxy-2-propanol 252.63
    pyridine 247.02
    3-pentanone 102.57
    furfural 328.9
    n-dodecane 1.19
    diethylene glycol 257.69
    diisopropyl ether 15.43
    tert-amyl alcohol 107.47
    acetylacetone 134.22
    n-hexadecane 1.32
    acetophenone 80.1
    methyl propionate 185.56
    isopentyl acetate 60.99
    trichloroethylene 999.97
    n-nonanol 16.98
    cyclohexanol 125.11
    benzyl alcohol 114.63
    2-ethylhexanol 37.59
    isooctanol 24.89
    dipropyl ether 34.21
    1,2-dichlorobenzene 115.61
    ethyl lactate 77.13
    propylene carbonate 150.34
    n-methylformamide 237.19
    2-pentanol 65.5
    n-pentane 4.9
    1-propoxy-2-propanol 102.32
    1-methoxy-2-propyl acetate 101.2
    2-(2-methoxypropoxy) propanol 82.53
    mesitylene 22.52
    ε-caprolactone 182.58
    p-cymene 19.29
    epichlorohydrin 423.47
    1,1,1-trichloroethane 301.78
    2-aminoethanol 304.15
    morpholine-4-carbaldehyde 235.05
    sulfolane 241.87
    2,2,4-trimethylpentane 4.98
    2-methyltetrahydrofuran 133.21
    n-hexyl acetate 33.4
    isooctane 2.13
    2-(2-butoxyethoxy)ethanol 123.91
    sec-butyl acetate 53.59
    tert-butyl acetate 63.26
    decalin 4.72
    glycerin 325.73
    diglyme 261.04
    acrylic acid 305.18
    isopropyl myristate 13.89
    n-butyric acid 329.06
    acetyl acetate 162.3
    di(2-ethylhexyl) phthalate 30.84
    ethyl propionate 80.69
    nitromethane 704.62
    1,2-diethoxyethane 89.86
    benzonitrile 90.63
    trioctyl phosphate 16.79
    1-bromopropane 153.77
    gamma-valerolactone 289.76
    n-decanol 13.05
    triethyl phosphate 45.21
    4-methyl-2-pentanol 32.87
    propionitrile 121.77
    vinylene carbonate 189.5
    1,1,2-trichlorotrifluoroethane 583.63
    DMS 64.26
    cumene 19.03
    2-octanol 12.42
    2-hexanone 60.54
    octyl acetate 20.26
    limonene 25.61
    1,2-dimethoxyethane 254.91
    ethyl orthosilicate 42.26
    tributyl phosphate 24.14
    diacetone alcohol 91.25
    N,N-dimethylaniline 43.88
    acrylonitrile 165.29
    aniline 163.49
    1,3-propanediol 325.31
    bromobenzene 122.06
    dibromomethane 531.09
    1,1,2,2-tetrachloroethane 711.3
    2-methyl-cyclohexyl acetate 55.76
    tetrabutyl urea 28.58
    diisobutyl methanol 18.2
    2-phenylethanol 82.09
    styrene 32.01
    dioctyl adipate 35.38
    dimethyl sulfate 124.08
    ethyl butyrate 64.26
    methyl lactate 122.33
    butyl lactate 44.78
    diethyl carbonate 56.79
    propanediol butyl ether 68.36
    triethyl orthoformate 51.44
    p-tert-butyltoluene 16.99
    methyl 4-tert-butylbenzoate 59.3
    morpholine 319.58
    tert-butylamine 46.49
    n-dodecanol 10.41
    dimethoxymethane 177.71
    ethylene carbonate 157.12
    cyrene 97.09
    2-ethoxyethyl acetate 75.83
    2-ethylhexyl acetate 46.68
    1,2,4-trichlorobenzene 154.93
    4-methylpyridine 169.48
    dibutyl ether 18.64
    2,6-dimethyl-4-heptanol 18.2
    DEF 158.62
    dimethyl isosorbide 119.99
    tetrachloroethylene 478.23
    eugenol 69.64
    triacetin 68.41
    span 80 60.71
    1,4-butanediol 145.88
    1,1-dichloroethane 350.81
    2-methyl-1-pentanol 101.67
    methyl formate 219.02
    2-methyl-1-butanol 133.57
    n-decane 1.86
    butyronitrile 113.87
    3,7-dimethyl-1-octanol 19.75
    1-chlorooctane 9.77
    1-chlorotetradecane 4.49
    n-nonane 1.62
    undecane 1.41
    tert-butylcyclohexane 3.8
    cyclooctane 3.69
    cyclopentanol 100.66
    tetrahydropyran 158.78
    tert-amyl methyl ether 61.2
    2,5,8-trioxanonane 163.66
    1-hexene 16.31
    2-isopropoxyethanol 166.83
    2,2,2-trifluoroethanol 325.77
    methyl butyrate 112.97

    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