(+-)-Laudanosine

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  • Identifiers

    CAS number
    1699-51-0

    Molecular formula
    C21H27NO4

    SMILES
    CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Vanilla 46.22%
    Spicy 42.88%
    Sweet 38.43%
    Phenolic 35.63%
    Smoky 30.64%
    Powdery 30.43%
    Floral 29.59%
    Balsamic 29.23%
    Animal 26.96%
    Woody 26.91%

     

    Flavor
    Bitter 85.07%
    Bland 24.89%
    Parsley 22.39%
    Cedarleaf 21.57%
    Sweet-like 20.93%
    Eugenol 20.74%
    Carrot 19.94%
    Lovage 19.51%
    Ripe apricot 19.47%
    Green pepper 19.47%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.7

    pKa est.
    7.21 (neutral)

    Molecular weight
    357.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    546°C

    Melting point expt.

    • 89 °C

    Flash point

    • 164.01 ˚C est.

  • Synonyms

    • 1699-51-0
    • (+-)-Laudanosine
    • RefChem:203703
    • DL-Laudanosine
    • 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
    • MFCD00006910
    • (R,S)-Laudanosine
    • Laudanosine (R,S)
    • 20412-65-1
    • 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
    • NSC35045
    • 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoqu inoline
    • Isoquinoline,1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1R)-
    • SMR000064381
    • EINECS 216-923-9
    • NSC 94267
    • Veraisoquin
    • dl-Laudanosin
    • AI3-61890
    • DL-Laudanoside
    • Laudanosine CRS
    • Prestwick_292
    • 5',8-Dimethoxylaudanosine hydrochloride
    • (A+/-)-Laudanosine
    • Spectrum_000863
    • (.+-.)-Laudanosine
    • SpecPlus_000088
    • Prestwick0_000591
    • Prestwick1_000591
    • Prestwick2_000591
    • Prestwick3_000591
    • Spectrum2_000663
    • Spectrum3_000112
    • Spectrum4_000934
    • Spectrum5_001625
    • (.+/-.)-Laudanosine
    • (+-)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
    • DL-Laudanosine, free base
    • DL-Laudanosine (Standard)
    • DL-​Laudanosine
    • CHEMBL1407
    • ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYL-, (+-)-
    • Oprea1_379167
    • BSPBio_000462
    • BSPBio_001724
    • KBioGR_001488
    • KBioSS_001343
    • MLS000060551
    • MLS002634637
    • DivK1c_006184
    • SCHEMBL466529
    • SPBio_000725
    • SPBio_002681
    • BPBio1_000510
    • orb1299152
    • SCHEMBL29822950
    • CHEBI:91599
    • KBio1_001128
    • KBio2_001343
    • KBio2_003911
    • KBio2_006479
    • KBio3_000864
    • DTXSID00871873
    • HMS1569H04
    • HMS2096H04
    • HMS2271K11
    • AAA08563
    • EX-A3381
    • NSC94267
    • BDBM50270376
    • CCG-38566
    • EBC-12786
    • NSC-94267
    • NSC331268
    • STL570293
    • AKOS001094404
    • AKOS022144164
    • FL52345
    • HY-122489R
    • NSC-331268
    • (1)-1-((3,4-Dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
    • 1,2,3,4-Tetrahydro-6,7-dimethoxy-1-(3,4-dimethoxybenzyl)-2-methylisoquinoline
    • NCGC00017301-02
    • NCGC00142367-01
    • AS-37336
    • Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (+-)-
    • ST023493
    • Atracurium EP Impurity G (DL-Laudanosine)
    • DB-043801
    • DB-180391
    • HY-122489
    • AB00052572
    • CS-0085743
    • NS00002032
    • EN300-180011
    • AB00052572-12
    • BRD-A24817035-001-05-4
    • Q27163429
    • Z57474215
    • Isoquinoline,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-
    • Cisatracurium Besylate Impurity 47; Atracurium Besilate EP Impurity G
    • (.+/-.)-1,2,3,4-Tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
    • Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (.+/-.)-
    • Isoquinoline,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (.+-.)-
    • Isoquinoline,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-
    • Laudanosine; 1-(3,4-dimethoxybenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline
    • Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (.+/-.)-
    • Isoquinoline,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (.+-.)-
    • 1699-51-0

  • Applications

    (+-)-Laudanosine (CAS 1699-51-0) is principally encountered as a metabolite and byproduct related to certain neuromuscular blocking agents (notably atracurium and cisatracurium) and is therefore of interest in pharmaceutical research and analytical chemistry. Practical applications include serving as a reference standard for LC-MS/HPLC methods to quantify laudanosine in biological samples or drug formulations; supporting metabolism and pharmacokinetic studies of neuromuscular blockers; informing toxicology and safety assessments in anesthesia-related research; acting as a synthetic intermediate in isoquinoline alkaloid chemistry for method development; and serving as an impurity marker for regulatory/compliance testing in drug product quality control, subject to local regulations and formulation limits.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 8.99
    methanol 8.25
    isopropanol 6.95
    water 0.08
    ethyl acetate 55.27
    n-propanol 10.81
    acetone 32.02
    n-butanol 9.93
    acetonitrile 25.18
    DMF 50.61
    toluene 11.35
    isobutanol 8.81
    1,4-dioxane 64.06
    methyl acetate 46.61
    THF 61.04
    2-butanone 37.09
    n-pentanol 11.68
    sec-butanol 8.42
    n-hexane 1.13
    ethylene glycol 4.79
    NMP 52.13
    cyclohexane 3.31
    DMSO 84.9
    n-butyl acetate 32.22
    n-octanol 6.58
    chloroform 284.92
    n-propyl acetate 36.39
    acetic acid 54.74
    dichloromethane 305.93
    cyclohexanone 61.54
    propylene glycol 3.11
    isopropyl acetate 29.83
    DMAc 82.93
    2-ethoxyethanol 49.3
    isopentanol 10.87
    n-heptane 1.94
    ethyl formate 40.13
    1,2-dichloroethane 153.3
    n-hexanol 11.72
    2-methoxyethanol 43.71
    isobutyl acetate 22.48
    tetrachloromethane 41.74
    n-pentyl acetate 25.66
    transcutol 74.63
    n-heptanol 9.23
    ethylbenzene 7.92
    MIBK 21.41
    2-propoxyethanol 46.11
    tert-butanol 10.83
    MTBE 13.22
    2-butoxyethanol 29.03
    propionic acid 25.84
    o-xylene 12.38
    formic acid 20.37
    diethyl ether 22.81
    m-xylene 9.68
    p-xylene 11.48
    chlorobenzene 34.72
    dimethyl carbonate 37.63
    n-octane 1.13
    formamide 38.39
    cyclopentanone 63.71
    2-pentanone 31.08
    anisole 21.76
    cyclopentyl methyl ether 29.12
    gamma-butyrolactone 96.39
    1-methoxy-2-propanol 26.72
    pyridine 42.98
    3-pentanone 33.04
    furfural 98.17
    n-dodecane 0.91
    diethylene glycol 41.46
    diisopropyl ether 7.94
    tert-amyl alcohol 11.01
    acetylacetone 55.56
    n-hexadecane 1.08
    acetophenone 33.55
    methyl propionate 45.5
    isopentyl acetate 31.41
    trichloroethylene 284.9
    n-nonanol 7.98
    cyclohexanol 14.91
    benzyl alcohol 20.45
    2-ethylhexanol 11.45
    isooctanol 9.4
    dipropyl ether 15.55
    1,2-dichlorobenzene 49.85
    ethyl lactate 21.57
    propylene carbonate 55.0
    n-methylformamide 32.94
    2-pentanol 7.12
    n-pentane 1.22
    1-propoxy-2-propanol 26.77
    1-methoxy-2-propyl acetate 45.63
    2-(2-methoxypropoxy) propanol 28.83
    mesitylene 7.35
    ε-caprolactone 61.78
    p-cymene 10.27
    epichlorohydrin 141.64
    1,1,1-trichloroethane 108.13
    2-aminoethanol 7.79
    morpholine-4-carbaldehyde 81.47
    sulfolane 111.51
    2,2,4-trimethylpentane 1.36
    2-methyltetrahydrofuran 37.79
    n-hexyl acetate 21.68
    isooctane 0.85
    2-(2-butoxyethoxy)ethanol 32.72
    sec-butyl acetate 23.46
    tert-butyl acetate 29.66
    decalin 2.25
    glycerin 10.1
    diglyme 86.74
    acrylic acid 30.4
    isopropyl myristate 10.47
    n-butyric acid 33.94
    acetyl acetate 56.57
    di(2-ethylhexyl) phthalate 14.46
    ethyl propionate 35.98
    nitromethane 125.08
    1,2-diethoxyethane 35.8
    benzonitrile 26.52
    trioctyl phosphate 9.68
    1-bromopropane 37.91
    gamma-valerolactone 104.09
    n-decanol 6.17
    triethyl phosphate 26.93
    4-methyl-2-pentanol 6.29
    propionitrile 22.69
    vinylene carbonate 65.18
    1,1,2-trichlorotrifluoroethane 123.53
    DMS 39.49
    cumene 7.7
    2-octanol 5.93
    2-hexanone 26.2
    octyl acetate 13.51
    limonene 11.8
    1,2-dimethoxyethane 73.91
    ethyl orthosilicate 24.83
    tributyl phosphate 13.52
    diacetone alcohol 27.91
    N,N-dimethylaniline 16.49
    acrylonitrile 32.9
    aniline 18.95
    1,3-propanediol 14.52
    bromobenzene 39.31
    dibromomethane 148.43
    1,1,2,2-tetrachloroethane 187.92
    2-methyl-cyclohexyl acetate 29.65
    tetrabutyl urea 16.67
    diisobutyl methanol 8.02
    2-phenylethanol 22.8
    styrene 9.01
    dioctyl adipate 20.45
    dimethyl sulfate 65.13
    ethyl butyrate 32.54
    methyl lactate 21.96
    butyl lactate 19.45
    diethyl carbonate 29.96
    propanediol butyl ether 14.35
    triethyl orthoformate 29.29
    p-tert-butyltoluene 8.77
    methyl 4-tert-butylbenzoate 32.16
    morpholine 59.09
    tert-butylamine 5.66
    n-dodecanol 4.87
    dimethoxymethane 57.59
    ethylene carbonate 57.47
    cyrene 42.3
    2-ethoxyethyl acetate 49.69
    2-ethylhexyl acetate 27.21
    1,2,4-trichlorobenzene 58.94
    4-methylpyridine 32.73
    dibutyl ether 10.87
    2,6-dimethyl-4-heptanol 8.02
    DEF 46.54
    dimethyl isosorbide 64.37
    tetrachloroethylene 141.93
    eugenol 30.32
    triacetin 40.41
    span 80 18.97
    1,4-butanediol 9.16
    1,1-dichloroethane 78.07
    2-methyl-1-pentanol 13.22
    methyl formate 39.08
    2-methyl-1-butanol 10.29
    n-decane 1.6
    butyronitrile 19.07
    3,7-dimethyl-1-octanol 8.26
    1-chlorooctane 6.44
    1-chlorotetradecane 3.11
    n-nonane 1.31
    undecane 1.15
    tert-butylcyclohexane 1.74
    cyclooctane 1.58
    cyclopentanol 14.38
    tetrahydropyran 34.56
    tert-amyl methyl ether 13.56
    2,5,8-trioxanonane 58.18
    1-hexene 3.92
    2-isopropoxyethanol 33.28
    2,2,2-trifluoroethanol 43.05
    methyl butyrate 41.81

    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