Cytisine

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  • Identifiers

    CAS number
    485-35-8

    Molecular formula
    C11H14N2O

    SMILES
    C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2

    Safety labels

    Acute Toxic
    Acute Toxic

    Irritant
    Irritant

  • Odor profile

    Fragrance
    Nutty 38.8%
    Animal 35.39%
    Odorless 33.48%
    Roasted 31.73%
    Fishy 28.92%
    Popcorn 28.85%
    Burnt 28.04%
    Musty 21.64%
    Meaty 21.52%
    Sweet 21.16%

     

    Flavor
    Bitter 86.92%
    Animal 22.57%
    Alkaline 20.98%
    Cereal 20.21%
    Cedarleaf 19.66%
    Indole 19.53%
    Shrimp 19.36%
    Very strong 19.33%
    Sweet-like 19.01%
    Moth ball 18.8%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    0.2

    pKa est.
    7.27 (neutral)

    Molecular weight
    190.24 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Melting point expt.

    • 152-153
    • 152-153 °C (sublimes)
    • MP: 155 °C

    Boiling point

    • 218
    • BP: 218 °C at 2 mm Hg

    Flash point

    • 161.93 ˚C est.

    Solubility expt.

    • Soluble in 13 parts acetone, 1.3 parts methanol, 3.5 parts alcohol, 30 parts benzene, 10 parts ethyl acetone, 2.0 parts chloroform; practically insoluble in petroleum ether
    • Soluble in 1.3 parts water
    • In water, 4.39X10+5 mg/L at 16 °C

  • Synonyms

    • CYTISINE
    • 485-35-8
    • Baptitoxine
    • Sophorine
    • Cytisinicline
    • Baptitoxin
    • Cytiton
    • Laburnin
    • Ulexine
    • Ulexin
    • Cytitone
    • Citizin
    • Cystisine
    • Cytizin
    • (1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One
    • 6039 Sopharma
    • citisiniclina
    • NSC-407282
    • 53S5U404NU
    • (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
    • CHEBI:4055
    • DTXSID00883395
    • 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-
    • (1R,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one
    • citizine
    • cystisin
    • cytisiniclinum
    • (1R,9S)-7,11-diazatricyclo(7.3.1.02,7)trideca-2,4-dien-6-one
    • (1R,9S)-7,11-diazatricyclo(7.3.1.0^(2,7))trideca-2,4-dien-6-one
    • (1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido(1,2-a)(1,5)diazocin-8-one
    • TBX-Free
    • RefChem:54921
    • DTXCID501022929
    • 207-616-0
    • (-)-Cytisine
    • Tabex
    • Tsitizin
    • Cytisin
    • Tabax
    • MFCD00136048
    • (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
    • Cytisine (-)
    • 1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
    • Cytisinicline [USAN]
    • CHEMBL497939
    • 1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
    • Baphitoxine
    • SMR001233264
    • HSDB 3560
    • MLS003171607
    • EINECS 207-616-0
    • NSC 407282
    • BRN 0083882
    • UNII-53S5U404NU
    • NSC407282
    • C5E
    • Prestwick_140
    • (?)-Cytisine
    • Cytisine ((+)-)
    • Tocris-1390
    • CYTISINE [HSDB]
    • CYTISINE [MI]
    • Cytisinicline (Standard)
    • 115051-74-6
    • Prestwick3_000624
    • CYTISINE [MART.]
    • CYTISINICLINE [INN]
    • BSPBio_000588
    • Cytisine, >=99%, powder
    • 5-24-02-00535 (Beilstein Handbook Reference)
    • MLS002153916
    • MLS002222174
    • SCHEMBL161398
    • CYTISINICLINE [WHO-DD]
    • BPBio1_000648
    • GTPL5347
    • orb1310572
    • (1R,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
    • (1S,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
    • HY-N0175R
    • 1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine)
    • Cytisine1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
    • HMS2096N10
    • HMS2235L06
    • HMS3267D20
    • HMS3414N03
    • HMS3678L21
    • HMS3884L11
    • HY-N0175
    • MSK40318
    • TNP00030
    • BDBM50143282
    • EBC-09113
    • HB2033
    • PDSP1_000461
    • s2287
    • WLN: T C666 A GVN LM&TTJ
    • AKOS000276818
    • AKOS015833102
    • CCG-208621
    • DB09028
    • FC09851
    • (1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one
    • NCGC00016463-01
    • NCGC00016463-02
    • NCGC00016463-03
    • NCGC00016463-04
    • NCGC00017171-01
    • NCGC00025138-01
    • NCGC00025138-02
    • NCGC00179513-01
    • AC-34317
    • AS-19539
    • CAS-485-35-8
    • SY057153
    • CS-0007888
    • NS00067015
    • SW219952-1
    • Cytisine, >=99.0% (HPLC), >=99%
    • EN300-224852
    • 485C358
    • F049425
    • Q417343
    • BRD-K74186897-001-02-5
    • BRD-K74186897-001-04-1
    • BRD-K74186897-001-10-8
    • BRD-K74186897-001-11-6
    • 485-35-8

  • Applications

    Cytisine (CAS 485-35-8) is a natural alkaloid sourced from Laburnum and Cytisus species and is used as the active pharmaceutical ingredient in some smoking cessation formulations. In pharmacology research, it serves as a tool to study effects on the nicotinic acetylcholine receptor and related signaling mechanisms. It is also produced from natural sources to supply research and development of alkaloid synthesis, and can function as a building block or intermediate for pharmaceutical synthesis and related scaffolds. In chemical applications, cytisine can be considered as a precursor for the synthesis of more complex alkaloids and related drug-like structures. Additionally, in agricultural science and applied biology research, cytisine is occasionally examined in studies on the biological activity and phytotoxicity of alkaloids in plants.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.83
    methanol 7.28
    isopropanol 2.68
    water 3.88
    ethyl acetate 4.46
    n-propanol 3.36
    acetone 3.84
    n-butanol 3.14
    acetonitrile 3.25
    DMF 22.61
    toluene 4.01
    isobutanol 3.67
    1,4-dioxane 9.19
    methyl acetate 3.18
    THF 7.89
    2-butanone 3.84
    n-pentanol 3.69
    sec-butanol 2.09
    n-hexane 0.08
    ethylene glycol 11.47
    NMP 35.84
    cyclohexane 0.25
    DMSO 34.64
    n-butyl acetate 6.03
    n-octanol 3.26
    chloroform 27.89
    n-propyl acetate 4.18
    acetic acid 21.95
    dichloromethane 29.84
    cyclohexanone 15.63
    propylene glycol 5.75
    isopropyl acetate 3.7
    DMAc 25.78
    2-ethoxyethanol 11.69
    isopentanol 4.19
    n-heptane 0.28
    ethyl formate 8.31
    1,2-dichloroethane 12.09
    n-hexanol 6.4
    2-methoxyethanol 17.81
    isobutyl acetate 3.95
    tetrachloromethane 3.93
    n-pentyl acetate 5.3
    transcutol 30.31
    n-heptanol 5.27
    ethylbenzene 2.31
    MIBK 4.32
    2-propoxyethanol 20.41
    tert-butanol 3.35
    MTBE 0.97
    2-butoxyethanol 13.37
    propionic acid 10.75
    o-xylene 4.97
    formic acid 32.35
    diethyl ether 0.91
    m-xylene 5.41
    p-xylene 3.55
    chlorobenzene 10.23
    dimethyl carbonate 4.97
    n-octane 0.19
    formamide 25.34
    cyclopentanone 15.37
    2-pentanone 3.68
    anisole 3.89
    cyclopentyl methyl ether 4.44
    gamma-butyrolactone 25.47
    1-methoxy-2-propanol 12.55
    pyridine 14.55
    3-pentanone 2.98
    furfural 50.6
    n-dodecane 0.27
    diethylene glycol 34.2
    diisopropyl ether 0.81
    tert-amyl alcohol 2.73
    acetylacetone 7.91
    n-hexadecane 0.32
    acetophenone 9.37
    methyl propionate 4.97
    isopentyl acetate 6.81
    trichloroethylene 35.56
    n-nonanol 3.51
    cyclohexanol 4.86
    benzyl alcohol 11.46
    2-ethylhexanol 4.73
    isooctanol 5.03
    dipropyl ether 1.84
    1,2-dichlorobenzene 14.25
    ethyl lactate 8.65
    propylene carbonate 20.22
    n-methylformamide 14.14
    2-pentanol 1.78
    n-pentane 0.1
    1-propoxy-2-propanol 12.04
    1-methoxy-2-propyl acetate 11.32
    2-(2-methoxypropoxy) propanol 16.04
    mesitylene 3.77
    ε-caprolactone 16.97
    p-cymene 4.38
    epichlorohydrin 23.52
    1,1,1-trichloroethane 7.38
    2-aminoethanol 10.67
    morpholine-4-carbaldehyde 35.18
    sulfolane 43.1
    2,2,4-trimethylpentane 0.22
    2-methyltetrahydrofuran 5.24
    n-hexyl acetate 5.63
    isooctane 0.21
    2-(2-butoxyethoxy)ethanol 18.22
    sec-butyl acetate 3.09
    tert-butyl acetate 4.04
    decalin 0.42
    glycerin 22.94
    diglyme 22.84
    acrylic acid 18.23
    isopropyl myristate 3.09
    n-butyric acid 13.81
    acetyl acetate 6.07
    di(2-ethylhexyl) phthalate 9.25
    ethyl propionate 3.61
    nitromethane 20.18
    1,2-diethoxyethane 4.89
    benzonitrile 15.22
    trioctyl phosphate 5.93
    1-bromopropane 2.54
    gamma-valerolactone 34.76
    n-decanol 2.95
    triethyl phosphate 6.57
    4-methyl-2-pentanol 2.56
    propionitrile 3.46
    vinylene carbonate 25.65
    1,1,2-trichlorotrifluoroethane 44.2
    DMS 7.6
    cumene 2.66
    2-octanol 2.79
    2-hexanone 3.72
    octyl acetate 4.1
    limonene 4.35
    1,2-dimethoxyethane 9.03
    ethyl orthosilicate 5.36
    tributyl phosphate 6.19
    diacetone alcohol 9.52
    N,N-dimethylaniline 4.64
    acrylonitrile 8.63
    aniline 8.48
    1,3-propanediol 11.84
    bromobenzene 9.34
    dibromomethane 12.55
    1,1,2,2-tetrachloroethane 26.09
    2-methyl-cyclohexyl acetate 7.9
    tetrabutyl urea 8.84
    diisobutyl methanol 3.35
    2-phenylethanol 15.29
    styrene 2.35
    dioctyl adipate 6.06
    dimethyl sulfate 13.86
    ethyl butyrate 5.1
    methyl lactate 11.59
    butyl lactate 10.54
    diethyl carbonate 4.85
    propanediol butyl ether 12.7
    triethyl orthoformate 5.13
    p-tert-butyltoluene 3.85
    methyl 4-tert-butylbenzoate 14.06
    morpholine 9.51
    tert-butylamine 1.47
    n-dodecanol 2.45
    dimethoxymethane 8.02
    ethylene carbonate 16.57
    cyrene 25.71
    2-ethoxyethyl acetate 9.19
    2-ethylhexyl acetate 5.77
    1,2,4-trichlorobenzene 18.02
    4-methylpyridine 11.51
    dibutyl ether 1.46
    2,6-dimethyl-4-heptanol 3.35
    DEF 7.96
    dimethyl isosorbide 24.58
    tetrachloroethylene 20.45
    eugenol 18.24
    triacetin 10.78
    span 80 14.81
    1,4-butanediol 7.88
    1,1-dichloroethane 6.57
    2-methyl-1-pentanol 4.51
    methyl formate 11.24
    2-methyl-1-butanol 3.65
    n-decane 0.31
    butyronitrile 4.11
    3,7-dimethyl-1-octanol 4.33
    1-chlorooctane 1.55
    1-chlorotetradecane 0.96
    n-nonane 0.24
    undecane 0.29
    tert-butylcyclohexane 0.38
    cyclooctane 0.2
    cyclopentanol 6.25
    tetrahydropyran 3.58
    tert-amyl methyl ether 1.28
    2,5,8-trioxanonane 23.04
    1-hexene 0.37
    2-isopropoxyethanol 8.37
    2,2,2-trifluoroethanol 17.46
    methyl butyrate 5.05

    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