Lobeline

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  • Identifiers

    CAS number
    90-69-7

    Molecular formula
    C22H27NO2

    SMILES
    CN1[C@@H](CCC[C@@H]1CC(=O)C2=CC=CC=C2)C[C@@H](C3=CC=CC=C3)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 35.77%
    Sweet 28.81%
    Balsamic 25.29%
    Animal 24.88%
    Cooling 22.67%
    Savory 22.59%
    Bitter 21.92%
    Herbal 21.77%
    Floral 20.5%
    Spicy 20.11%

     

    Flavor
    Bitter 58.87%
    Fruity 30.97%
    Odorless 26.67%
    Sweet 25.49%
    Mild 22.35%
    Sweet-like 20.06%
    Cedarleaf 19.8%
    Orange flower 19.76%
    Nitrile 19.76%
    Orange blossom 19.68%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    3.8

    pKa est.
    7.62 (neutral)

    Molecular weight
    337.5 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    533°C

    Melting point expt.

    • 130.5 °C

    Flash point

    • 192.11 ˚C est.

  • Synonyms

    • lobeline
    • (-)-Lobeline
    • Inflatine
    • alpha-Lobeline
    • Lobnico
    • Lobelinum
    • Lobelin
    • 90-69-7
    • Lobelina
    • 8,10-Diphenyllobelionol
    • 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
    • DTXSID3023219
    • D0P25S3P81
    • 2-(6-(2-Hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenylethanone
    • 2-(6-(beta-Hydroxyphenethyl)-1-methyl-2-piperidyl)acetophenone
    • NSC-757421
    • 2-{(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethanone
    • DTXCID603219
    • CHEBI:48723
    • Ethanone, 2-(6-(2-hydroxy-2-phenylethyl)-1-methyl-2-piperidinyl)-1-phenyl-, (2R-(2alpha,6alpha(S*)))-
    • 2-(6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
    • 2-[6-(2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl]-1-phenylethanone
    • 2-((2R,6S)-6-((2S)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethanone
    • RefChem:153874
    • GlyTouCan:G34337IT
    • G34337IT
    • 202-012-3
    • Lobeline [INN]
    • .alpha.-Lobeline
    • CHEMBL122270
    • alpha-Lobeline hydrochloride
    • Lobeline (INN)
    • NCGC00024378-05
    • 2-((2R,6S)-6-((S)-2-hydroxy-2-phenylethyl)-1-methylpiperidin-2-yl)-1-phenylethan-1-one
    • Lobeline [INN:BAN]
    • Lobelinum [INN-Latin]
    • Lobelina [INN-Spanish]
    • UNII-D0P25S3P81
    • SR-01000075960
    • L0B
    • EINECS 202-012-3
    • Lobeline alpha (-)
    • NSC36866
    • BRN 0091533
    • LOBELINE [MI]
    • LOBELINUM [HPUS]
    • Prestwick0_000585
    • Prestwick1_000585
    • Prestwick2_000585
    • Prestwick3_000585
    • LOBELINE [WHO-DD]
    • Lopac0_000698
    • BSPBio_000430
    • 5-21-12-00627 (Beilstein Handbook Reference)
    • SCHEMBL290803
    • SPBio_002649
    • BPBio1_000474
    • orb1685081
    • GTPL13498
    • MXYUKLILVYORSK-HBMCJLEFSA-N
    • Tox21_110900
    • BDBM50080818
    • AKOS024278800
    • CCG-204783
    • DB05137
    • NSC 757421
    • SDCCGSBI-0050676.P002
    • CAS-90-69-7
    • NCGC00024378-06
    • NCGC00024378-07
    • NCGC00024378-08
    • NCGC00024378-09
    • NCGC00024378-10
    • NCGC00024378-14
    • DA-48561
    • AB00489926
    • NS00001152
    • C07475
    • D02364
    • Q421905
    • SR-01000075960-5
    • BRD-K66206289-003-03-1
    • BRD-K66206289-003-09-8
    • BRD-K66206289-003-20-5
    • BRD-K66206289-003-21-3
    • 2-(6-(.BETA.-HYDROXYPHENETHYL)-1-METHYL-2-PIPERIDYL)ACETOPHENONE
    • 2-[(2R,6S)-6-[(2R)-2-hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl]-1-phenylethanone
    • 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenyl-ethyl]-1-methyl-2-piperidyl]-1-phenyl-ethanone
    • 2-{(2R,6S)-6-[(2S)-2-Hydroxy-2-phenylethyl]-1-methylpiperidin-2-yl}-1-phenylethan-1-one
    • Ethanone, 2-[(2R,6S)-6-[(2S)-2-hydroxy-2-phenylethyl]-1-methyl-2-piperidinyl]-1-phenyl-
    • 2-((2R,6S)-6-((2S)-2-HYDROXY-2-PHENYLETHYL)-1-METHYL-2-PIPERIDINYL)-1-PHENYLETHANONE
    • 90-69-7

  • Applications

    Lobeline (CAS 90-69-7) is a natural piperidine alkaloid isolated from Lobelia inflata. In research and manufacturing contexts, its primary applications are as a pharmacology research tool and an analytical reference: it is used in receptor pharmacology studies to probe nicotinic acetylcholine receptors and related monoamine transport systems (including VMAT2); as a reference standard for the quantitative analysis of alkaloids in plant material and natural product extracts (typically by HPLC or GC); it can serve as a synthetic building block or intermediate in the preparation of piperidine alkaloids for exploratory chemical studies; and it has been investigated historically as a nicotine substitute in smoking-cessation research, though it is not an approved product and its use is subject to regulatory controls. In practice, lobeline is supplied for laboratory research and analytical applications under appropriate safety and regulatory constraints.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 21.32
    methanol 44.99
    isopropanol 8.58
    water 0.22
    ethyl acetate 25.62
    n-propanol 17.21
    acetone 31.06
    n-butanol 14.97
    acetonitrile 9.22
    DMF 57.64
    toluene 21.27
    isobutanol 9.13
    1,4-dioxane 73.32
    methyl acetate 24.51
    THF 75.75
    2-butanone 34.34
    n-pentanol 11.24
    sec-butanol 5.82
    n-hexane 0.17
    ethylene glycol 5.3
    NMP 26.54
    cyclohexane 0.59
    DMSO 94.84
    n-butyl acetate 19.07
    n-octanol 4.03
    chloroform 137.89
    n-propyl acetate 18.43
    acetic acid 47.02
    dichloromethane 114.12
    cyclohexanone 59.93
    propylene glycol 8.11
    isopropyl acetate 16.85
    DMAc 131.87
    2-ethoxyethanol 42.7
    isopentanol 13.65
    n-heptane 0.37
    ethyl formate 22.69
    1,2-dichloroethane 79.05
    n-hexanol 10.78
    2-methoxyethanol 67.49
    isobutyl acetate 13.63
    tetrachloromethane 6.67
    n-pentyl acetate 10.87
    transcutol 197.05
    n-heptanol 7.18
    ethylbenzene 7.18
    MIBK 17.86
    2-propoxyethanol 48.52
    tert-butanol 9.23
    MTBE 5.99
    2-butoxyethanol 28.96
    propionic acid 20.18
    o-xylene 10.34
    formic acid 25.99
    diethyl ether 9.74
    m-xylene 11.21
    p-xylene 8.74
    chlorobenzene 30.75
    dimethyl carbonate 20.7
    n-octane 0.2
    formamide 40.62
    cyclopentanone 56.12
    2-pentanone 24.0
    anisole 19.02
    cyclopentyl methyl ether 18.85
    gamma-butyrolactone 63.25
    1-methoxy-2-propanol 39.94
    pyridine 63.86
    3-pentanone 22.87
    furfural 68.12
    n-dodecane 0.23
    diethylene glycol 43.66
    diisopropyl ether 2.54
    tert-amyl alcohol 6.36
    acetylacetone 44.89
    n-hexadecane 0.28
    acetophenone 26.81
    methyl propionate 26.69
    isopentyl acetate 19.74
    trichloroethylene 164.28
    n-nonanol 5.16
    cyclohexanol 11.75
    benzyl alcohol 23.84
    2-ethylhexanol 7.01
    isooctanol 6.49
    dipropyl ether 8.46
    1,2-dichlorobenzene 28.57
    ethyl lactate 15.22
    propylene carbonate 32.6
    n-methylformamide 30.1
    2-pentanol 5.64
    n-pentane 0.18
    1-propoxy-2-propanol 27.72
    1-methoxy-2-propyl acetate 36.54
    2-(2-methoxypropoxy) propanol 30.89
    mesitylene 5.37
    ε-caprolactone 41.13
    p-cymene 5.48
    epichlorohydrin 108.02
    1,1,1-trichloroethane 32.63
    2-aminoethanol 14.55
    morpholine-4-carbaldehyde 61.1
    sulfolane 70.73
    2,2,4-trimethylpentane 0.31
    2-methyltetrahydrofuran 20.79
    n-hexyl acetate 11.25
    isooctane 0.24
    2-(2-butoxyethoxy)ethanol 46.26
    sec-butyl acetate 12.87
    tert-butyl acetate 17.04
    decalin 0.65
    glycerin 19.49
    diglyme 103.0
    acrylic acid 21.95
    isopropyl myristate 5.94
    n-butyric acid 32.61
    acetyl acetate 25.04
    di(2-ethylhexyl) phthalate 10.62
    ethyl propionate 16.23
    nitromethane 79.7
    1,2-diethoxyethane 36.67
    benzonitrile 20.82
    trioctyl phosphate 5.65
    1-bromopropane 14.6
    gamma-valerolactone 102.66
    n-decanol 3.97
    triethyl phosphate 13.37
    4-methyl-2-pentanol 5.64
    propionitrile 12.13
    vinylene carbonate 41.2
    1,1,2-trichlorotrifluoroethane 81.24
    DMS 19.59
    cumene 4.94
    2-octanol 3.2
    2-hexanone 16.99
    octyl acetate 7.3
    limonene 6.02
    1,2-dimethoxyethane 64.23
    ethyl orthosilicate 12.54
    tributyl phosphate 7.67
    diacetone alcohol 26.16
    N,N-dimethylaniline 13.57
    acrylonitrile 19.78
    aniline 28.32
    1,3-propanediol 26.86
    bromobenzene 28.26
    dibromomethane 52.96
    1,1,2,2-tetrachloroethane 122.1
    2-methyl-cyclohexyl acetate 17.87
    tetrabutyl urea 11.46
    diisobutyl methanol 4.71
    2-phenylethanol 22.47
    styrene 9.41
    dioctyl adipate 13.14
    dimethyl sulfate 33.05
    ethyl butyrate 18.11
    methyl lactate 21.01
    butyl lactate 14.94
    diethyl carbonate 15.11
    propanediol butyl ether 18.36
    triethyl orthoformate 17.26
    p-tert-butyltoluene 4.79
    methyl 4-tert-butylbenzoate 25.2
    morpholine 64.78
    tert-butylamine 3.48
    n-dodecanol 2.97
    dimethoxymethane 62.43
    ethylene carbonate 33.64
    cyrene 32.39
    2-ethoxyethyl acetate 28.58
    2-ethylhexyl acetate 14.67
    1,2,4-trichlorobenzene 34.63
    4-methylpyridine 38.13
    dibutyl ether 6.23
    2,6-dimethyl-4-heptanol 4.71
    DEF 30.47
    dimethyl isosorbide 58.24
    tetrachloroethylene 69.98
    eugenol 27.54
    triacetin 24.05
    span 80 20.24
    1,4-butanediol 9.77
    1,1-dichloroethane 37.72
    2-methyl-1-pentanol 11.43
    methyl formate 27.42
    2-methyl-1-butanol 10.26
    n-decane 0.38
    butyronitrile 11.51
    3,7-dimethyl-1-octanol 5.62
    1-chlorooctane 2.2
    1-chlorotetradecane 1.1
    n-nonane 0.27
    undecane 0.29
    tert-butylcyclohexane 0.52
    cyclooctane 0.23
    cyclopentanol 9.39
    tetrahydropyran 33.59
    tert-amyl methyl ether 5.49
    2,5,8-trioxanonane 68.55
    1-hexene 1.47
    2-isopropoxyethanol 25.56
    2,2,2-trifluoroethanol 19.7
    methyl butyrate 22.57

    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