Papaverine

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  • Identifiers

    CAS number
    58-74-2

    Molecular formula
    C20H21NO4

    SMILES
    COC1=C(C=C(C=C1)CC2=NC=CC3=CC(=C(C=C32)OC)OC)OC

    Safety labels

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Floral 54.07%
    Spicy 51.15%
    Vanilla 47.72%
    Sweet 44.77%
    Phenolic 40.39%
    Powdery 40.13%
    Smoky 32.97%
    Balsamic 32.81%
    Woody 32.8%
    Animal 28.84%

     

    Flavor
    Bitter 83.55%
    Parsley 22.92%
    Eugenol 21.92%
    Bland 21.0%
    Cedarleaf 20.51%
    Carrot 20.36%
    Sweet-like 19.68%
    Very strong 19.63%
    Lovage 19.5%
    Allspice 19.46%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.9

    pKa est.
    6.0 (neutral)

    Molecular weight
    339.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 226 (dec) °C
    • 147.5 °C
    • White, monoclinic prisms from water. MP: 224.5 °C; Very soluble in water, ethanol /Papaverine hydrochloride/

    Boiling point

    • Sublimes at 135 °C

    Flash point

    • 186.61 ˚C est.

    Solubility expt.

    • In water, 3.733X10-5 mg/L at 37.5 °C
    • Slightly soluble in water; very soluble in ethanol, chloroform; soluble in acetone, benzene, pyridine
    • Almost insoluble in water. Soluble in hot benzene, glacial acetic acid, acetone; slightly soluble in chloroform, carbon tetrachloride, petroleum ether
    • In water, 35 mg/L at 17 °C
    • 1.29e-02 g/L

  • Synonyms

    • papaverine
    • 58-74-2
    • Robaxapap
    • 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline
    • 6,7-Dimethoxy-1-veratrylisoquinoline
    • 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxyisoquinoline
    • Pavacap
    • Papaverinum
    • Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-
    • DAA13NKG2Q
    • 1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyisoquinoline
    • NSC-136630
    • Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-
    • DTXSID4023418
    • Pavatym
    • CHEBI:28241
    • NSC136630
    • RefChem:56338
    • DTXCID603418
    • 200-397-2
    • Papaverin
    • Papanerine
    • Papanerin
    • Papaverina
    • Cerespan
    • Pavabid
    • Papaverine [BAN]
    • Papaverine free base
    • NSC 136630
    • Isoquinoline, 6,7-dimethoxy-1-veratryl-
    • S-M-R
    • Papaverine (BAN)
    • 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinoline
    • 58-74-2 (free base)
    • CHEMBL19224
    • 4-[(6,7-Dimethoxyisoquinolyl)methyl]-1,2-dimethoxybenzene
    • HSDB 3147
    • Pavacot
    • Papaverina [Italian]
    • Ceraspan
    • Mesotina (TN)
    • EV1
    • CAS-61-25-6
    • NCGC00015810-02
    • EINECS 200-397-2
    • UNII-DAA13NKG2Q
    • BRN 0312930
    • Pavadyl
    • 2wey
    • RS 47
    • TNP00305
    • 6,7-Dimethoxy-1-(3,4-dimethoxybenzyl)isoquinoline
    • Noscapine Impurity 4
    • Spectrum_000071
    • PAPAVERINE [MI]
    • Prestwick0_000583
    • Prestwick1_000583
    • Prestwick2_000583
    • Prestwick3_000583
    • Spectrum2_000978
    • Spectrum3_000537
    • Spectrum4_000467
    • Spectrum5_001188
    • Lopac-P-3510
    • PAPAVERINE [VANDF]
    • PAPAVERINUM [HPUS]
    • Isoquinoline, 6,7-dimethoxy-1-veratryl-(8Cl)
    • PAPAVERINE [MART.]
    • PAPAVERINE [WHO-DD]
    • Lopac0_000957
    • Oprea1_387689
    • Oprea1_810508
    • SCHEMBL34702
    • BSPBio_000426
    • BSPBio_002153
    • KBioGR_000914
    • KBioSS_000471
    • 5-21-06-00182 (Beilstein Handbook Reference)
    • DivK1c_000321
    • SPBio_001015
    • SPBio_002645
    • BPBio1_000470
    • MEGxp0_001880
    • SCHEMBL29360983
    • SCHEMBL29387160
    • ACon1_000238
    • ACon1_002094
    • BDBM14754
    • GTPL13147
    • KBio1_000321
    • KBio2_000471
    • KBio2_003039
    • KBio2_005607
    • KBio3_001653
    • 1-[(3,4-Dimethoxyphenyl)methyl]6,7-dimethoxyisoquinoline
    • NINDS_000321
    • HMS3561N11
    • HMS3746M21
    • ALBB-010475
    • 1-{[3,4-bis(methyloxy)phenyl]methyl}-6,7-bis(methyloxy)isoquinoline
    • BBL012345
    • EBC-26648
    • MFCD00024138
    • STK039035
    • Isoquinoline,7-dimethoxy-1-veratryl-
    • AKOS000277460
    • CCG-202821
    • CS-7800
    • DB01113
    • KS-5336
    • SDCCGMLS-0003037.P003
    • SDCCGSBI-0050931.P005
    • IDI1_000321
    • NCGC00015810-01
    • NCGC00015810-03
    • NCGC00015810-04
    • NCGC00015810-05
    • NCGC00015810-06
    • NCGC00015810-07
    • NCGC00015810-08
    • NCGC00015810-09
    • NCGC00015810-13
    • NCGC00015810-24
    • NCGC00015810-29
    • NCGC00024428-03
    • NCGC00024428-04
    • HY-18077
    • papaverine

  • Applications

    Papaverine is primarily encountered in pharmaceutical R&D as a synthetic intermediate for benzylisoquinoline/isoquinoline alkaloids and related derivatives; it is also used as a reference standard and analytical reagent for quantifying opium alkaloids in quality-control methods (for example, HPLC/GC); in academic and industrial organic laboratories it serves as a reagent for synthesis and for structure-activity investigations of isoquinoline alkaloids; it can be supplied as a starting material for bespoke synthesis of specific derivatives in research projects.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.56
    methanol 2.71
    isopropanol 3.01
    water 0.02
    ethyl acetate 20.96
    n-propanol 4.55
    acetone 15.81
    n-butanol 4.07
    acetonitrile 15.23
    DMF 18.49
    toluene 4.24
    isobutanol 3.67
    1,4-dioxane 29.58
    methyl acetate 18.55
    THF 51.68
    2-butanone 14.82
    n-pentanol 5.79
    sec-butanol 4.07
    n-hexane 1.61
    ethylene glycol 1.59
    NMP 16.77
    cyclohexane 2.85
    DMSO 51.88
    n-butyl acetate 12.04
    n-octanol 3.31
    chloroform 85.88
    n-propyl acetate 16.12
    acetic acid 19.97
    dichloromethane 131.36
    cyclohexanone 23.98
    propylene glycol 0.76
    isopropyl acetate 12.59
    DMAc 29.84
    2-ethoxyethanol 19.88
    isopentanol 4.58
    n-heptane 2.32
    ethyl formate 12.6
    1,2-dichloroethane 70.87
    n-hexanol 5.19
    2-methoxyethanol 14.86
    isobutyl acetate 9.64
    tetrachloromethane 13.8
    n-pentyl acetate 11.54
    transcutol 29.92
    n-heptanol 4.53
    ethylbenzene 4.26
    MIBK 9.49
    2-propoxyethanol 17.09
    tert-butanol 5.06
    MTBE 6.83
    2-butoxyethanol 11.69
    propionic acid 9.28
    o-xylene 4.39
    formic acid 7.03
    diethyl ether 15.07
    m-xylene 3.3
    p-xylene 5.87
    chlorobenzene 9.53
    dimethyl carbonate 12.89
    n-octane 1.26
    formamide 16.4
    cyclopentanone 29.9
    2-pentanone 12.51
    anisole 9.53
    cyclopentyl methyl ether 16.2
    gamma-butyrolactone 42.17
    1-methoxy-2-propanol 8.98
    pyridine 22.33
    3-pentanone 14.4
    furfural 35.51
    n-dodecane 0.77
    diethylene glycol 13.89
    diisopropyl ether 4.65
    tert-amyl alcohol 5.42
    acetylacetone 21.31
    n-hexadecane 0.89
    acetophenone 13.24
    methyl propionate 16.87
    isopentyl acetate 12.03
    trichloroethylene 105.55
    n-nonanol 4.05
    cyclohexanol 6.01
    benzyl alcohol 7.54
    2-ethylhexanol 5.22
    isooctanol 4.4
    dipropyl ether 12.41
    1,2-dichlorobenzene 14.72
    ethyl lactate 7.04
    propylene carbonate 17.81
    n-methylformamide 10.59
    2-pentanol 3.33
    n-pentane 1.27
    1-propoxy-2-propanol 10.03
    1-methoxy-2-propyl acetate 16.18
    2-(2-methoxypropoxy) propanol 11.56
    mesitylene 2.52
    ε-caprolactone 23.07
    p-cymene 4.65
    epichlorohydrin 73.41
    1,1,1-trichloroethane 36.35
    2-aminoethanol 2.53
    morpholine-4-carbaldehyde 27.08
    sulfolane 47.27
    2,2,4-trimethylpentane 0.86
    2-methyltetrahydrofuran 23.89
    n-hexyl acetate 9.66
    isooctane 0.49
    2-(2-butoxyethoxy)ethanol 13.73
    sec-butyl acetate 10.32
    tert-butyl acetate 13.39
    decalin 1.58
    glycerin 2.87
    diglyme 40.23
    acrylic acid 10.7
    isopropyl myristate 4.89
    n-butyric acid 11.13
    acetyl acetate 18.24
    di(2-ethylhexyl) phthalate 5.43
    ethyl propionate 16.42
    nitromethane 48.42
    1,2-diethoxyethane 18.59
    benzonitrile 9.32
    trioctyl phosphate 3.83
    1-bromopropane 20.03
    gamma-valerolactone 37.0
    n-decanol 3.24
    triethyl phosphate 11.92
    4-methyl-2-pentanol 2.81
    propionitrile 11.51
    vinylene carbonate 19.59
    1,1,2-trichlorotrifluoroethane 39.5
    DMS 14.83
    cumene 3.92
    2-octanol 3.28
    2-hexanone 12.94
    octyl acetate 5.85
    limonene 5.41
    1,2-dimethoxyethane 41.73
    ethyl orthosilicate 11.39
    tributyl phosphate 5.36
    diacetone alcohol 11.26
    N,N-dimethylaniline 8.67
    acrylonitrile 14.98
    aniline 5.75
    1,3-propanediol 5.03
    bromobenzene 11.15
    dibromomethane 64.47
    1,1,2,2-tetrachloroethane 66.61
    2-methyl-cyclohexyl acetate 13.4
    tetrabutyl urea 7.45
    diisobutyl methanol 4.12
    2-phenylethanol 8.38
    styrene 4.1
    dioctyl adipate 9.05
    dimethyl sulfate 24.47
    ethyl butyrate 15.48
    methyl lactate 6.2
    butyl lactate 6.87
    diethyl carbonate 13.5
    propanediol butyl ether 4.99
    triethyl orthoformate 13.43
    p-tert-butyltoluene 3.84
    methyl 4-tert-butylbenzoate 13.42
    morpholine 27.02
    tert-butylamine 3.35
    n-dodecanol 2.62
    dimethoxymethane 26.13
    ethylene carbonate 17.36
    cyrene 16.37
    2-ethoxyethyl acetate 20.22
    2-ethylhexyl acetate 10.42
    1,2,4-trichlorobenzene 17.07
    4-methylpyridine 11.79
    dibutyl ether 7.73
    2,6-dimethyl-4-heptanol 4.12
    DEF 17.22
    dimethyl isosorbide 28.69
    tetrachloroethylene 53.27
    eugenol 12.62
    triacetin 15.19
    span 80 7.74
    1,4-butanediol 3.42
    1,1-dichloroethane 27.67
    2-methyl-1-pentanol 6.35
    methyl formate 11.84
    2-methyl-1-butanol 4.47
    n-decane 1.42
    butyronitrile 9.18
    3,7-dimethyl-1-octanol 3.73
    1-chlorooctane 4.28
    1-chlorotetradecane 1.96
    n-nonane 1.24
    undecane 0.99
    tert-butylcyclohexane 1.13
    cyclooctane 1.2
    cyclopentanol 6.94
    tetrahydropyran 21.14
    tert-amyl methyl ether 7.09
    2,5,8-trioxanonane 25.59
    1-hexene 3.95
    2-isopropoxyethanol 14.27
    2,2,2-trifluoroethanol 14.88
    methyl butyrate 17.28

    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