Prilocaine

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  • Identifiers

    CAS number
    721-50-6

    Molecular formula
    C13H20N2O

    SMILES
    CCCNC(C)C(=O)NC1=CC=CC=C1C

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Odorless 44.34%
    Fishy 41.1%
    Savory 38.33%
    Meaty 34.91%
    Cooling 31.6%
    Cheesy 31.31%
    Animal 25.65%
    Ripe 25.61%
    Cooked 24.02%
    Roasted 22.34%

     

    Flavor
    Odorless 37.4%
    Mild 30.7%
    Bitter 26.98%
    Bland 22.7%
    Nitrile 20.12%
    Bloody 19.25%
    Roasted 19.24%
    Glue 19.2%
    Sweet-like 19.14%
    Creosote 19.08%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.1

    pKa est.
    6.71 (neutral)

    Molecular weight
    220.31 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 37-38 °C
    • 37 - 38 °C

    Boiling point

    • 159-162 °C at 1.00E-01 mm Hg
    • 159-162 °C @ 1 mm Hg

    Flash point

    • 157.72 ˚C est.

    Solubility expt.

    • 541 mg/L
    • Crystals from ethanol + isopropyl ether; readily sol in water; mp 167-168 °C /Hydrochloride/
    • FREELY SOL IN ALC; SLIGHTLY SOL IN CHLOROFORM
    • VERY SLIGHTLY SOL IN ACETONE; PRACTICALLY INSOL IN ETHER
    • 3.26e-01 g/L

  • Synonyms

    • prilocaine
    • 721-50-6
    • Propitocaine
    • Citanest
    • prilocaine base
    • Prilocaina
    • Prilocainum
    • N-(2-Methylphenyl)-2-(propylamino)propanamide
    • Astra 1515
    • Propanamide, N-(2-methylphenyl)-2-(propylamino)-
    • o-Methyl-2-propylaminopropionanilide
    • 2-(Propylamino)-o-propionotoluidide
    • o-Propionotoluidide, 2-(propylamino)-
    • Astra 1512
    • o-Methyl-alpha-propylaminopropionanilide
    • 2-Methyl-alpha-propylaminopropionanilide
    • alpha-n-Propylamino-2-methylpropionanilide
    • Prilocainum [INN-Latin]
    • Prilocaina [INN-Spanish]
    • (+/-)-Prilocaine
    • NSC 40027
    • Prilotekal
    • CHEBI:8404
    • HSDB 3386
    • o-Propionotoluidide, 2-propylamino-
    • EINECS 211-957-0
    • NSC-40027
    • BRN 2108498
    • Propitocaine (JAN)
    • ASTRA-1512
    • ASTRA-1515
    • UNII-046O35D44R
    • 2-Methyl-.alpha.-propylaminopropionanilide
    • 046O35D44R
    • L 67
    • N-(2-methylphenyl)-N(2)-propylalaninamide
    • DL-(+/-)-PRILOCAINE
    • EMLA COMPONENT PRILOCAINE
    • DTXSID7031955
    • ORAQIX COMPONENT PRILOCAINE
    • Prilocaine [USAN:USP:INN:BAN]
    • FORTACIN COMPONENT PRILOCAINE
    • NSC40027
    • o-Propionotuluidide, 2-propylamino-
    • Prilocaine [USAN]
    • Prilocainum (INN-Latin)
    • Prilocaina (INN-Spanish)
    • PROPITOCAINE [JAN]
    • PRILOCAINE (MART.)
    • PRILOCAINE [MART.]
    • PRILOCAINE (USP-RS)
    • PRILOCAINE [USP-RS]
    • (+/-)-N-(2-PROPYLAMINOPROPIONYL)-2-TOLUIDINE
    • N-(2,6-DIMETHYLPHENYL)-2-(PROPYLAMINO)PROPANAMIDE
    • PRILOCAINE (EP MONOGRAPH)
    • PRILOCAINE [EP MONOGRAPH]
    • (R)-Prilocaine
    • (S)-Prilocaine
    • PRILOCAINE (USP MONOGRAPH)
    • PRILOCAINE [USP MONOGRAPH]
    • Prilocaine (USAN:USP:INN:BAN)
    • 2-(Propylamino)-N-(o-tolyl)propanamide
    • Prilocaine (USP/INN)
    • Prilocain
    • MFCD00048681
    • Prilocaine (Standard)
    • N-(2-methylphenyl)-N2-propylalaninamide
    • Spectrum_001649
    • PRILOCAINE [MI]
    • PRILOCAINE [INN]
    • Prestwick0_000199
    • Prestwick1_000199
    • Prestwick2_000199
    • Prestwick3_000199
    • Spectrum2_001549
    • Spectrum3_001052
    • Spectrum4_001192
    • Spectrum5_001175
    • (.+/-.)-Prilocaine
    • PRILOCAINE [HSDB]
    • PRILOCAINE [VANDF]
    • CHEMBL1194
    • PRILOCAINE [WHO-DD]
    • Lopac0_001005
    • SCHEMBL25467
    • BSPBio_000157
    • BSPBio_002604
    • KBioGR_001883
    • KBioSS_002129
    • DivK1c_000846
    • SPBio_001398
    • SPBio_002078
    • BPBio1_000173
    • GTPL7276
    • DTXCID5011955
    • PRILOCAINE [ORANGE BOOK]
    • HY-B0137R
    • KBio1_000846
    • KBio2_002129
    • KBio2_004697
    • KBio2_007265
    • KBio3_001824
    • N01BB04
    • NINDS_000846
    • HMS3604H09
    • HMS3651M13
    • HMS3884A04
    • HY-B0137
    • PAA28931
    • PAA28932
    • PRILOCAINE COMPONENT OF EMLA
    • BDBM50225477
    • s1619
    • STL257086
    • PRILOCAINE COMPONENT OF ORAQIX
    • AKOS015889404
    • AC-2100
    • CCG-205085
    • CS-1929
    • DB00750
    • PRILOCAINE COMPONENT OF FORTACIN
    • SDCCGSBI-0050978.P004
    • IDI1_000846
    • NCGC00015860-02
    • NCGC00015860-03
    • NCGC00015860-15
    • NCGC00162312-01
    • AS-14851

  • Applications

    Prilocaine (CAS 721-50-6) is an amide-type local anesthetic used in pharmaceutical formulations to produce nerve-block analgesia. In clinical practice, it is employed as injectable local anesthesia for dental procedures, often in combination with epinephrine to extend the duration of action. It is also formulated in topical anesthetic products for dermatological and cosmetic procedures, and may be used in veterinary medicine as a local anesthetic agent.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 163.7
    methanol 266.15
    isopropanol 86.15
    water 1.63
    ethyl acetate 111.91
    n-propanol 102.81
    acetone 136.79
    n-butanol 97.99
    acetonitrile 56.56
    DMF 301.66
    toluene 24.73
    isobutanol 75.36
    1,4-dioxane 149.98
    methyl acetate 90.9
    THF 142.87
    2-butanone 105.35
    n-pentanol 79.5
    sec-butanol 73.23
    n-hexane 1.63
    ethylene glycol 52.76
    NMP 173.62
    cyclohexane 3.0
    DMSO 275.94
    n-butyl acetate 117.12
    n-octanol 31.89
    chloroform 280.4
    n-propyl acetate 73.37
    acetic acid 224.52
    dichloromethane 266.64
    cyclohexanone 161.49
    propylene glycol 68.62
    isopropyl acetate 80.54
    DMAc 366.05
    2-ethoxyethanol 131.59
    isopentanol 92.68
    n-heptane 1.27
    ethyl formate 100.12
    1,2-dichloroethane 156.47
    n-hexanol 81.12
    2-methoxyethanol 208.68
    isobutyl acetate 61.92
    tetrachloromethane 19.36
    n-pentyl acetate 51.0
    transcutol 356.36
    n-heptanol 42.95
    ethylbenzene 21.26
    MIBK 64.61
    2-propoxyethanol 157.33
    tert-butanol 97.17
    MTBE 67.1
    2-butoxyethanol 94.63
    propionic acid 100.77
    o-xylene 26.59
    formic acid 112.31
    diethyl ether 42.78
    m-xylene 24.68
    p-xylene 32.91
    chlorobenzene 70.69
    dimethyl carbonate 40.85
    n-octane 1.26
    formamide 133.92
    cyclopentanone 168.97
    2-pentanone 90.65
    anisole 52.49
    cyclopentyl methyl ether 52.52
    gamma-butyrolactone 177.3
    1-methoxy-2-propanol 135.61
    pyridine 113.82
    3-pentanone 67.31
    furfural 199.11
    n-dodecane 1.66
    diethylene glycol 145.19
    diisopropyl ether 13.95
    tert-amyl alcohol 82.44
    acetylacetone 118.23
    n-hexadecane 1.86
    acetophenone 72.91
    methyl propionate 75.3
    isopentyl acetate 107.81
    trichloroethylene 308.23
    n-nonanol 29.94
    cyclohexanol 57.08
    benzyl alcohol 68.77
    2-ethylhexanol 45.36
    isooctanol 36.95
    dipropyl ether 23.2
    1,2-dichlorobenzene 73.88
    ethyl lactate 50.49
    propylene carbonate 129.86
    n-methylformamide 123.57
    2-pentanol 50.88
    n-pentane 1.29
    1-propoxy-2-propanol 100.33
    1-methoxy-2-propyl acetate 100.71
    2-(2-methoxypropoxy) propanol 82.94
    mesitylene 16.37
    ε-caprolactone 137.55
    p-cymene 18.45
    epichlorohydrin 200.01
    1,1,1-trichloroethane 87.52
    2-aminoethanol 96.84
    morpholine-4-carbaldehyde 180.67
    sulfolane 230.98
    2,2,4-trimethylpentane 3.01
    2-methyltetrahydrofuran 93.02
    n-hexyl acetate 60.19
    isooctane 2.04
    2-(2-butoxyethoxy)ethanol 113.89
    sec-butyl acetate 55.04
    tert-butyl acetate 73.25
    decalin 4.19
    glycerin 99.22
    diglyme 194.55
    acrylic acid 103.7
    isopropyl myristate 23.36
    n-butyric acid 181.09
    acetyl acetate 87.17
    di(2-ethylhexyl) phthalate 40.51
    ethyl propionate 55.32
    nitromethane 235.91
    1,2-diethoxyethane 94.8
    benzonitrile 71.2
    trioctyl phosphate 26.87
    1-bromopropane 47.55
    gamma-valerolactone 239.19
    n-decanol 23.37
    triethyl phosphate 38.96
    4-methyl-2-pentanol 39.85
    propionitrile 52.19
    vinylene carbonate 125.9
    1,1,2-trichlorotrifluoroethane 175.82
    DMS 65.69
    cumene 20.61
    2-octanol 24.48
    2-hexanone 67.17
    octyl acetate 32.03
    limonene 24.01
    1,2-dimethoxyethane 165.54
    ethyl orthosilicate 37.52
    tributyl phosphate 32.42
    diacetone alcohol 89.16
    N,N-dimethylaniline 43.74
    acrylonitrile 76.03
    aniline 56.79
    1,3-propanediol 137.1
    bromobenzene 64.53
    dibromomethane 137.71
    1,1,2,2-tetrachloroethane 255.59
    2-methyl-cyclohexyl acetate 60.29
    tetrabutyl urea 41.69
    diisobutyl methanol 24.1
    2-phenylethanol 77.43
    styrene 25.26
    dioctyl adipate 41.06
    dimethyl sulfate 79.13
    ethyl butyrate 67.25
    methyl lactate 62.39
    butyl lactate 55.05
    diethyl carbonate 51.47
    propanediol butyl ether 85.63
    triethyl orthoformate 48.41
    p-tert-butyltoluene 16.84
    methyl 4-tert-butylbenzoate 65.27
    morpholine 157.16
    tert-butylamine 47.31
    n-dodecanol 18.35
    dimethoxymethane 107.19
    ethylene carbonate 106.18
    cyrene 92.78
    2-ethoxyethyl acetate 88.17
    2-ethylhexyl acetate 79.04
    1,2,4-trichlorobenzene 85.97
    4-methylpyridine 100.39
    dibutyl ether 26.78
    2,6-dimethyl-4-heptanol 24.1
    DEF 116.33
    dimethyl isosorbide 130.57
    tetrachloroethylene 151.46
    eugenol 78.4
    triacetin 67.27
    span 80 70.82
    1,4-butanediol 66.83
    1,1-dichloroethane 107.66
    2-methyl-1-pentanol 80.23
    methyl formate 99.4
    2-methyl-1-butanol 80.4
    n-decane 2.22
    butyronitrile 65.85
    3,7-dimethyl-1-octanol 33.74
    1-chlorooctane 14.71
    1-chlorotetradecane 6.87
    n-nonane 1.74
    undecane 1.87
    tert-butylcyclohexane 4.08
    cyclooctane 1.18
    cyclopentanol 59.08
    tetrahydropyran 93.34
    tert-amyl methyl ether 47.2
    2,5,8-trioxanonane 133.77
    1-hexene 11.35
    2-isopropoxyethanol 92.88
    2,2,2-trifluoroethanol 76.43
    methyl butyrate 90.75

    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