Arecoline

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  • Identifiers

    CAS number
    63-75-2

    Molecular formula
    C8H13NO2

    SMILES
    CN1CCC=C(C1)C(=O)OC

    Safety labels

    Irritant
    Irritant

    Health Hazard
    Health

  • Odor profile

    Fragrance
    Sweet 35.75%
    Fruity 30.56%
    Nutty 29.55%
    Mint 28.11%
    Herbal 27.3%
    Floral 25.01%
    Odorless 24.31%
    Caramellic 24.24%
    Green 23.2%
    Roasted 22.81%

     

    Flavor
    Fruity 43.83%
    Bitter 41.78%
    Orange flower 20.83%
    Extremely sweet 20.74%
    Taco 20.69%
    Cotton candy 20.51%
    Seedy 20.4%
    Ripe apricot 20.3%
    Mildew 20.27%
    Lovage 20.14%

     

    Odor impact est.
    Medium

  • Properties

    XLogP3-AA
    0.3

    pKa est.
    7.19 (neutral)

    Molecular weight
    155.19 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Moderately fast

    Melting point expt.

    • < 25 °C

    Boiling point

    • 209 °C
    • 209.00 °C. @ 760.00 mm Hg

    Flash point

    • 92.39 ˚C est.

    Solubility expt.

    • 1000000 mg/L (at 25 °C)
    • 1.00E+06 mg/L @ 25 °C (exp)

  • Synonyms

    • arecoline
    • 63-75-2
    • Arecolin
    • Arecaline
    • Arecholine
    • Methylarecaiden
    • Methylarecaidin
    • Arekolin
    • Arecoline base
    • Arecaidine methyl ester
    • 3-Pyridinecarboxylic acid, 1,2,5,6-tetrahydro-1-methyl-, methyl ester
    • methyl 1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate
    • Arecholin
    • methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate
    • Methyl N-methyltetrahydronicotinate
    • N-Methyltetrahydronicotinic acid, methyl ester
    • Methyl 1,2,5,6-tetrahydro-1-methylnicotinate
    • Methyl N-methyl-1,2,5,6-tetrahydronicotinate
    • DTXSID3022617
    • NSC-56321
    • 1,2,5,6-Tetrahydro-1-methylnicotinic acid, methyl ester
    • Taeniolin
    • 4ALN5933BH
    • NICOTINIC ACID, 1,2,5,6-TETRAHYDRO-1-METHYL-, METHYL ESTER
    • CHEBI:2814
    • DTXCID502617
    • methyl 1-methyl-5,6-dihydro-2H-pyridine-3-carboxylate
    • RefChem:559924
    • 200-565-5
    • C8H13NO2
    • NSC 56321
    • MFCD00059167
    • 1,2,5,6-Tetrahydro-1-methyl-3-pyridinecarboxylic acid methyl ester
    • 1-Methyl-delta(sup 3,4)tetrahydro-3-pyridinecarboxylate
    • 63-75-2 (free)
    • 1-Methyl-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid methyl ester
    • NCGC00015075-04
    • N-Methyl-.delta.-tetrahydronicotinic acid methyl ester
    • N-Methyltetrahydropyridine-.beta.-carboxylic acid methyl ester
    • MLS000028840
    • Arecaidine methyl ester;Arecoline base;Methyl arecaidin; Methylarecaidine; NSC56321
    • CAS-63-75-2
    • CCRIS 7688
    • SMR000058258
    • EINECS 200-565-5
    • BRN 0123045
    • UNII-4ALN5933BH
    • Methylarecaidine
    • arecoline;hydrobromide
    • methyl 1-methyl-3,6-dihydro-2H-pyridine-5-carboxylate;hydrobromide
    • Spectrum_000055
    • N-Methyltetrahydropyridine-beta-carboxylic acid methyl ester
    • ARECOLINE [MI]
    • Prestwick0_000402
    • Prestwick1_000402
    • Prestwick2_000402
    • Prestwick3_000402
    • Spectrum2_000051
    • Spectrum3_001387
    • Spectrum4_000810
    • Spectrum5_001316
    • Lopac-A-6134
    • cid_9301
    • CHEMBL7303
    • Lopac0_000049
    • SCHEMBL44065
    • BSPBio_000324
    • BSPBio_002974
    • GTPL296
    • KBioGR_001299
    • KBioSS_000435
    • DivK1c_000810
    • SPBio_000201
    • SPBio_002263
    • BPBio1_000358
    • MEGxp0_001891
    • orb1740527
    • ACon1_002372
    • BDBM46858
    • KBio1_000810
    • KBio2_000435
    • KBio2_003003
    • KBio2_005571
    • KBio3_002194
    • pyranosyl)-?-D-galactopyranoside
    • NINDS_000810
    • WLN: T6N CUTJ A1 CVO1
    • ALBB-035732
    • NSC56321
    • Tox21_110079
    • BBL036229
    • EBC-44394
    • MSK170173
    • AKOS000520752
    • Tox21_110079_1
    • CCG-204145
    • DB04365
    • SB54186
    • SDCCGMLS-0066647.P001
    • SDCCGSBI-0050038.P004
    • IDI1_000810
    • NCGC00015075-01
    • NCGC00015075-02
    • NCGC00015075-03
    • NCGC00015075-05
    • NCGC00015075-06
    • NCGC00015075-07
    • NCGC00015075-10
    • NCGC00015075-19
    • NCGC00162053-01
    • NCGC00162053-02
    • NCGC00162053-03
    • AC-34025
    • CAS-300-08-3
    • ST095172
    • SBI-0050038.P003
    • Methyl N-methyl-1,5,6-tetrahydronicotinate
    • N-Methyl-beta -carboxylic acid methyl ester
    • CS-0022545
    • Methyl 1,5,6-tetrahydro-1-methylnicotinate
    • NS00002617
    • EN300-40737
    • AB00053580_08
    • AB00053580_09
    • Methyl 1,2,5, 6-tetrahydro-1-methylnicotinate
    • Methyl N-methyl-1,2,5, 6-tetrahydronicotinate
    • methyl-1,2,5,6-tetrahydro-1-methyl nicotinate
    • 63-75-2

  • Applications

    Arecoline (CAS 63-75-2) is principally used in pharmaceutical and biological research as a muscarinic receptor agonist, enabling evaluation of cholinergic signaling and receptor activity in various tissues; it also serves as an intermediate in the synthesis of related cholinergic compounds and as a scaffold for designing alkaloid derivatives in medicinal chemistry. In analytical laboratories, arecoline may be used as a reference standard or analytical reagent for assays measuring cholinergic activity or for qualitative and quantitative method development. Due to its toxicity and pharmacological activity, its applications are mainly confined to research settings and are subject to local regulations and formulation limits. Additionally, it may function as an educational/reference material in chemical biology studies related to the cholinergic system.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 130.88
    methanol 220.8
    isopropanol 71.21
    water 23.41
    ethyl acetate 21.49
    n-propanol 92.57
    acetone 23.69
    n-butanol 67.4
    acetonitrile 37.08
    DMF 177.88
    toluene 22.62
    isobutanol 59.2
    1,4-dioxane 107.45
    methyl acetate 32.15
    THF 52.33
    2-butanone 24.33
    n-pentanol 43.63
    sec-butanol 52.33
    n-hexane 0.65
    ethylene glycol 161.71
    NMP 112.22
    cyclohexane 3.11
    DMSO 99.65
    n-butyl acetate 16.11
    n-octanol 18.61
    chloroform 208.91
    n-propyl acetate 12.89
    acetic acid 187.69
    dichloromethane 168.66
    cyclohexanone 50.27
    propylene glycol 105.1
    isopropyl acetate 10.39
    DMAc 107.62
    2-ethoxyethanol 96.84
    isopentanol 42.62
    n-heptane 1.21
    ethyl formate 52.38
    1,2-dichloroethane 57.66
    n-hexanol 43.17
    2-methoxyethanol 209.03
    isobutyl acetate 11.05
    tetrachloromethane 31.67
    n-pentyl acetate 12.13
    transcutol 117.04
    n-heptanol 24.44
    ethylbenzene 11.32
    MIBK 11.74
    2-propoxyethanol 88.07
    tert-butanol 63.95
    MTBE 14.8
    2-butoxyethanol 52.84
    propionic acid 87.01
    o-xylene 23.3
    formic acid 273.23
    diethyl ether 11.78
    m-xylene 19.0
    p-xylene 15.76
    chlorobenzene 43.91
    dimethyl carbonate 18.09
    n-octane 0.75
    formamide 196.63
    cyclopentanone 48.88
    2-pentanone 14.94
    anisole 28.31
    cyclopentyl methyl ether 20.41
    gamma-butyrolactone 70.19
    1-methoxy-2-propanol 93.02
    pyridine 91.13
    3-pentanone 12.93
    furfural 140.14
    n-dodecane 1.01
    diethylene glycol 136.09
    diisopropyl ether 3.29
    tert-amyl alcohol 46.77
    acetylacetone 19.67
    n-hexadecane 1.15
    acetophenone 34.19
    methyl propionate 24.72
    isopentyl acetate 17.08
    trichloroethylene 158.73
    n-nonanol 16.87
    cyclohexanol 52.25
    benzyl alcohol 58.27
    2-ethylhexanol 21.44
    isooctanol 18.63
    dipropyl ether 8.26
    1,2-dichlorobenzene 45.74
    ethyl lactate 27.79
    propylene carbonate 54.39
    n-methylformamide 128.63
    2-pentanol 25.23
    n-pentane 1.17
    1-propoxy-2-propanol 44.36
    1-methoxy-2-propyl acetate 23.92
    2-(2-methoxypropoxy) propanol 45.21
    mesitylene 11.47
    ε-caprolactone 52.8
    p-cymene 11.94
    epichlorohydrin 84.21
    1,1,1-trichloroethane 49.05
    2-aminoethanol 178.1
    morpholine-4-carbaldehyde 140.0
    sulfolane 87.25
    2,2,4-trimethylpentane 1.61
    2-methyltetrahydrofuran 35.8
    n-hexyl acetate 18.29
    isooctane 1.05
    2-(2-butoxyethoxy)ethanol 59.26
    sec-butyl acetate 8.9
    tert-butyl acetate 12.85
    decalin 2.25
    glycerin 184.15
    diglyme 92.35
    acrylic acid 110.57
    isopropyl myristate 8.35
    n-butyric acid 83.06
    acetyl acetate 18.93
    di(2-ethylhexyl) phthalate 21.43
    ethyl propionate 12.89
    nitromethane 115.05
    1,2-diethoxyethane 18.43
    benzonitrile 56.8
    trioctyl phosphate 12.64
    1-bromopropane 22.13
    gamma-valerolactone 98.1
    n-decanol 12.7
    triethyl phosphate 16.92
    4-methyl-2-pentanol 15.48
    propionitrile 37.97
    vinylene carbonate 79.64
    1,1,2-trichlorotrifluoroethane 160.36
    DMS 20.9
    cumene 10.92
    2-octanol 11.92
    2-hexanone 12.49
    octyl acetate 12.37
    limonene 13.2
    1,2-dimethoxyethane 71.63
    ethyl orthosilicate 15.59
    tributyl phosphate 13.02
    diacetone alcohol 33.24
    N,N-dimethylaniline 25.35
    acrylonitrile 66.32
    aniline 59.69
    1,3-propanediol 177.03
    bromobenzene 36.92
    dibromomethane 84.77
    1,1,2,2-tetrachloroethane 120.32
    2-methyl-cyclohexyl acetate 21.95
    tetrabutyl urea 18.9
    diisobutyl methanol 11.94
    2-phenylethanol 48.57
    styrene 14.44
    dioctyl adipate 17.37
    dimethyl sulfate 34.12
    ethyl butyrate 15.2
    methyl lactate 44.67
    butyl lactate 23.1
    diethyl carbonate 16.22
    propanediol butyl ether 53.7
    triethyl orthoformate 16.28
    p-tert-butyltoluene 11.12
    methyl 4-tert-butylbenzoate 34.95
    morpholine 124.16
    tert-butylamine 30.8
    n-dodecanol 9.77
    dimethoxymethane 52.25
    ethylene carbonate 52.97
    cyrene 62.33
    2-ethoxyethyl acetate 21.87
    2-ethylhexyl acetate 13.45
    1,2,4-trichlorobenzene 59.14
    4-methylpyridine 66.21
    dibutyl ether 6.94
    2,6-dimethyl-4-heptanol 11.94
    DEF 36.94
    dimethyl isosorbide 60.73
    tetrachloroethylene 94.06
    eugenol 48.74
    triacetin 25.61
    span 80 44.17
    1,4-butanediol 78.19
    1,1-dichloroethane 52.43
    2-methyl-1-pentanol 34.23
    methyl formate 85.1
    2-methyl-1-butanol 46.63
    n-decane 1.36
    butyronitrile 39.33
    3,7-dimethyl-1-octanol 17.09
    1-chlorooctane 6.73
    1-chlorotetradecane 3.43
    n-nonane 1.08
    undecane 1.15
    tert-butylcyclohexane 2.01
    cyclooctane 1.19
    cyclopentanol 57.46
    tetrahydropyran 41.51
    tert-amyl methyl ether 14.32
    2,5,8-trioxanonane 72.45
    1-hexene 3.48
    2-isopropoxyethanol 48.1
    2,2,2-trifluoroethanol 102.23
    methyl butyrate 19.57

    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