Yohimbine

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  • Identifiers

    CAS number
    146-48-5

    Molecular formula
    C21H26N2O3

    SMILES
    COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 45.18%
    Animal 26.97%
    Sweet 26.55%
    Floral 26.26%
    Grape 23.91%
    Nutty 21.57%
    Fruity 21.53%
    Bitter 19.72%
    Fresh 18.54%
    Vanilla 18.21%

     

    Flavor
    Bitter 89.81%
    Odorless 21.68%
    Sweet-like 21.56%
    Cedarleaf 20.8%
    Bland 20.27%
    Alkaline 19.95%
    Cereal 19.83%
    Indole 19.43%
    Very strong 19.41%
    Nitrile 18.98%

     

    Odor impact est.
    Low

  • Properties

    XLogP3-AA
    2.9

    pKa est.
    7.5 (neutral)

    Molecular weight
    354.4 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    786°C

    Melting point expt.

    • 241 °C

    Flash point

    • 251.91 ˚C est.

    Solubility expt.

    • 3.48e-01 g/L

  • Synonyms

    • Yohimbine
    • 146-48-5
    • Yohimbin
    • Quebrachine
    • Corynine
    • Quebrachin
    • APHRODINE
    • Yohimbic acid methyl ester
    • (+)-Yohimbine
    • Yohimbinum
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-
    • 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester
    • 2Y49VWD90Q
    • DTXSID9040130
    • methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
    • (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester
    • DTXCID7020130
    • CHEBI:10093
    • methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
    • methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo(11.8.0.0^(2,10).0^(4,9).0^(15,20))henicosa-2(10),4,6,8-tetraene-19-carboxylate
    • Tartrate, Corynanthine
    • RefChem:56477
    • 205-672-0
    • Aphrosol
    • Johimbin
    • MFCD00005093
    • 17-Hydroxyyohimban-16-carboxylic acid methyl ester
    • methyl 17alpha-hydroxyyohimban-16alpha-carboxylate
    • CHEMBL15245
    • Actibine
    • YOHIMBINE CHLORIDE
    • CHEMBL537669
    • Yohimbine (DCF)
    • CAS-146-48-5
    • methyl hydroxy[?]carboxylate
    • EINECS 205-672-0
    • 17?-Hydroxy-yohimban-16?-carboxylic Acid Methyl Ester
    • BRN 0097276
    • trans-Quinolizidine yohimbine
    • UNII-2Y49VWD90Q
    • CCRIS 9415
    • SR-01000075297
    • Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
    • NSC19509
    • YOHIMBINE [MI]
    • Prestwick0_000584
    • Prestwick1_000584
    • Prestwick2_000584
    • Prestwick3_000584
    • Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester
    • YOHIMBINE [VANDF]
    • YOHIMBINUM [HPUS]
    • cid_6169
    • cid_8969
    • YOHIMBE HYDROCHLORIDE
    • YOHIMBINE [WHO-DD]
    • Lopac0_001210
    • SCHEMBL33954
    • BSPBio_000428
    • BSPBio_001236
    • GTPL102
    • KBioGR_000576
    • KBioSS_000576
    • 17alpha-hydroxy-yohimban-16alpha-carboxylic acid methyl ester
    • 4-25-00-01237 (Beilstein Handbook Reference)
    • MLS000728591
    • SPBio_002647
    • BPBio1_000472
    • orb1685173
    • Yohimbol-16alpha-carboxylic acid, methyl ester (6CI)
    • SCHEMBL29385789
    • BCBcMAP01_000032
    • KBio2_000576
    • KBio2_003144
    • KBio2_005712
    • KBio3_001031
    • KBio3_001032
    • Bio1_000455
    • Bio1_000944
    • Bio1_001433
    • Bio2_000458
    • Bio2_000938
    • HMS1362N17
    • HMS1792N17
    • HMS1990N17
    • HMS2089G19
    • HMS2234C18
    • Tox21_110019
    • BDBM50013515
    • BDBM50203564
    • EBC-26708
    • AKOS015902024
    • Tox21_110019_1
    • Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester
    • Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI)
    • CCG-205284
    • CS-5173
    • DB01392
    • FY01219
    • GS-5751
    • SDCCGSBI-0051177.P002
    • IDI1_002213
    • MRF-0000020
    • SMP1_000320
    • NCGC00013260-01
    • NCGC00025018-05
    • NCGC00025018-06
    • NCGC00025018-07
    • NCGC00025018-10
    • NCGC00025018-11
    • NCGC00025018-16
    • NCGC00025018-17
    • NCGC00025018-24
    • NCGC00025018-29
    • HY-12715
    • SMR000470778
    • 17a-hydroxy-16a-methoxycarbonyl-yohimbane
    • NS00003970
    • 65Y190
    • C09256
    • D08685
    • H10057
    • EN300-19731915
    • Q412226
    • SR-01000075297-5
    • BRD-K35586044-001-02-6
    • BRD-K35586044-003-03-0
    • 146-48-5

  • Applications

    Yohimbine (CAS 146-48-5) is mainly used as a tool in pharmaceutical and biochemical research to study alpha-2 adrenergic receptor pharmacology and related signaling; it also serves as a chemical synthesis intermediate for related alkaloids and research APIs; in analytical laboratories, yohimbine is used as a reference standard for methods such as HPLC/LC-MS for identification and quantification in test samples; in some markets it is present in nutraceutical or dietary supplement formulations as yohimbine hydrochloride under local regulatory controls; additionally, it is used as a reference material to support method development and process optimization in chemical synthesis.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 1.72
    methanol 4.12
    isopropanol 1.23
    water 0.02
    ethyl acetate 1.35
    n-propanol 1.49
    acetone 2.84
    n-butanol 2.11
    acetonitrile 0.46
    DMF 6.97
    toluene 0.64
    isobutanol 1.31
    1,4-dioxane 3.66
    methyl acetate 1.21
    THF 4.29
    2-butanone 2.91
    n-pentanol 1.54
    sec-butanol 0.67
    n-hexane 0.02
    ethylene glycol 1.22
    NMP 4.4
    cyclohexane 0.03
    DMSO 10.59
    n-butyl acetate 2.79
    n-octanol 1.19
    chloroform 4.46
    n-propyl acetate 2.1
    acetic acid 6.58
    dichloromethane 2.98
    cyclohexanone 7.54
    propylene glycol 0.72
    isopropyl acetate 1.66
    DMAc 13.27
    2-ethoxyethanol 9.38
    isopentanol 2.71
    n-heptane 0.03
    ethyl formate 2.28
    1,2-dichloroethane 1.82
    n-hexanol 1.78
    2-methoxyethanol 14.46
    isobutyl acetate 2.33
    tetrachloromethane 0.65
    n-pentyl acetate 5.04
    transcutol 27.85
    n-heptanol 2.37
    ethylbenzene 0.34
    MIBK 3.07
    2-propoxyethanol 12.84
    tert-butanol 1.12
    MTBE 0.43
    2-butoxyethanol 13.62
    propionic acid 1.72
    o-xylene 0.47
    formic acid 7.01
    diethyl ether 0.48
    m-xylene 0.61
    p-xylene 0.54
    chlorobenzene 1.17
    dimethyl carbonate 1.97
    n-octane 0.03
    formamide 7.76
    cyclopentanone 5.95
    2-pentanone 2.99
    anisole 1.11
    cyclopentyl methyl ether 1.21
    gamma-butyrolactone 5.29
    1-methoxy-2-propanol 8.26
    pyridine 3.58
    3-pentanone 1.7
    furfural 11.24
    n-dodecane 0.03
    diethylene glycol 15.76
    diisopropyl ether 0.23
    tert-amyl alcohol 0.81
    acetylacetone 5.14
    n-hexadecane 0.04
    acetophenone 3.05
    methyl propionate 1.5
    isopentyl acetate 4.06
    trichloroethylene 6.19
    n-nonanol 1.57
    cyclohexanol 1.13
    benzyl alcohol 3.27
    2-ethylhexanol 1.1
    isooctanol 2.23
    dipropyl ether 0.57
    1,2-dichlorobenzene 1.46
    ethyl lactate 3.12
    propylene carbonate 3.84
    n-methylformamide 4.07
    2-pentanol 0.76
    n-pentane 0.02
    1-propoxy-2-propanol 6.58
    1-methoxy-2-propyl acetate 5.74
    2-(2-methoxypropoxy) propanol 9.82
    mesitylene 0.38
    ε-caprolactone 5.64
    p-cymene 0.56
    epichlorohydrin 7.42
    1,1,1-trichloroethane 1.37
    2-aminoethanol 1.89
    morpholine-4-carbaldehyde 11.4
    sulfolane 9.38
    2,2,4-trimethylpentane 0.03
    2-methyltetrahydrofuran 1.26
    n-hexyl acetate 3.99
    isooctane 0.03
    2-(2-butoxyethoxy)ethanol 14.41
    sec-butyl acetate 1.4
    tert-butyl acetate 1.97
    decalin 0.04
    glycerin 4.7
    diglyme 22.23
    acrylic acid 2.69
    isopropyl myristate 1.37
    n-butyric acid 4.46
    acetyl acetate 1.76
    di(2-ethylhexyl) phthalate 3.99
    ethyl propionate 1.34
    nitromethane 8.0
    1,2-diethoxyethane 3.61
    benzonitrile 2.82
    trioctyl phosphate 2.43
    1-bromopropane 0.55
    gamma-valerolactone 18.68
    n-decanol 1.01
    triethyl phosphate 2.01
    4-methyl-2-pentanol 1.02
    propionitrile 0.85
    vinylene carbonate 4.98
    1,1,2-trichlorotrifluoroethane 16.79
    DMS 3.47
    cumene 0.35
    2-octanol 1.1
    2-hexanone 2.82
    octyl acetate 2.1
    limonene 0.54
    1,2-dimethoxyethane 9.07
    ethyl orthosilicate 1.81
    tributyl phosphate 2.51
    diacetone alcohol 5.33
    N,N-dimethylaniline 0.97
    acrylonitrile 1.62
    aniline 1.63
    1,3-propanediol 6.51
    bromobenzene 0.87
    dibromomethane 1.45
    1,1,2,2-tetrachloroethane 4.45
    2-methyl-cyclohexyl acetate 2.93
    tetrabutyl urea 3.71
    diisobutyl methanol 0.76
    2-phenylethanol 4.49
    styrene 0.34
    dioctyl adipate 3.08
    dimethyl sulfate 4.36
    ethyl butyrate 1.77
    methyl lactate 3.57
    butyl lactate 7.25
    diethyl carbonate 1.5
    propanediol butyl ether 8.42
    triethyl orthoformate 2.12
    p-tert-butyltoluene 0.5
    methyl 4-tert-butylbenzoate 6.46
    morpholine 3.53
    tert-butylamine 0.32
    n-dodecanol 0.65
    dimethoxymethane 6.28
    ethylene carbonate 4.04
    cyrene 10.02
    2-ethoxyethyl acetate 10.13
    2-ethylhexyl acetate 2.74
    1,2,4-trichlorobenzene 2.2
    4-methylpyridine 2.91
    dibutyl ether 0.77
    2,6-dimethyl-4-heptanol 0.76
    DEF 3.07
    dimethyl isosorbide 12.46
    tetrachloroethylene 4.16
    eugenol 10.01
    triacetin 5.95
    span 80 6.88
    1,4-butanediol 2.25
    1,1-dichloroethane 1.1
    2-methyl-1-pentanol 1.94
    methyl formate 3.74
    2-methyl-1-butanol 1.64
    n-decane 0.06
    butyronitrile 1.14
    3,7-dimethyl-1-octanol 1.29
    1-chlorooctane 0.35
    1-chlorotetradecane 0.15
    n-nonane 0.04
    undecane 0.04
    tert-butylcyclohexane 0.03
    cyclooctane 0.02
    cyclopentanol 0.98
    tetrahydropyran 1.26
    tert-amyl methyl ether 0.46
    2,5,8-trioxanonane 15.41
    1-hexene 0.11
    2-isopropoxyethanol 5.96
    2,2,2-trifluoroethanol 4.23
    methyl butyrate 2.27

    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