Rauwolscine hydrochloride

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  • Identifiers

    CAS number
    6211-32-1

    Molecular formula
    C21H27ClN2O3

    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.Cl

    Safety labels

    Acute Toxic
    Acute Toxic

  • Odor profile

    Fragrance
    Odorless 62.21%
    Animal 28.35%
    Phenolic 23.71%
    Bitter 23.41%
    Sweet 19.98%
    Nutty 19.67%
    Musty 18.96%
    Cooling 17.84%
    Earthy 17.65%
    Mint 17.35%

     

    Flavor
    Bitter 82.57%
    Fruity 23.92%
    Odorless 21.97%
    Cedarleaf 21.55%
    Sweet-like 21.3%
    Alkaline 21.0%
    Orange flower 20.86%
    Cereal 20.54%
    Indole 20.44%
    Very strong 20.39%

     

    Odor impact est.
    Low

  • Properties

    pKa est.
    -411040.25 (strong acid)

    Molecular weight
    390.9 g/mol

    Vapor pressure est.

    • hPa @ 20°C
    • hPa @ 25°C

    Evaporation rate
    Ultra slow

    Boiling point est.
    801°C

    Flash point

    • 157.04 ˚C est.

  • Synonyms

    • Rauwolscine hydrochloride
    • 6211-32-1
    • alpha-Yohimbine hydrochloride
    • Rauwolscine HCl
    • alpha-Yohimbin hydrochloride
    • EINECS 228-279-6
    • UNII-PQ323MIB24
    • NSC 407307
    • PQ323MIB24
    • .ALPHA.-YOHIMBINE HYDROCHLORIDE
    • NSC-407307
    • YOHIMBINE HYDROCHLORIDE, .ALPHA.-
    • .ALPHA.-YOHIMBINE HYDROCHLORIDE [MI]
    • 20-alpha-Yohimban-16-beta-carboxylic acid, 17-alpha-hydroxy-, methyl ester, hydrochloride
    • 20alpha-Yohimban-16beta-carboxylic acid, 17alpha-hydroxy-, methyl ester, monohydrochloride
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16beta,17alpha,20alpha)-
    • YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, HYDROCHLORIDE (1:1), (16.BETA.,17.ALPHA.,20.ALPHA.)-
    • RefChem:178664
    • YOHIMBINE HYDROCHLORIDE, ALPHA-
    • 20alpha-Yohimban-16beta-carboxylic acid, 17alpha-hydroxy-, methyl ester, monohydrochloride (8CI)
    • 228-279-6
    • YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, HYDROCHLORIDE (1:1), (16BETA,17ALPHA,20ALPHA)-
    • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16beta,17alpha,20alpha)-(9CI)
    • Fauwolscine, hydrochloride
    • Methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate hydrochloride
    • Rauwolscine (hydrochloride)
    • C21H27ClN2O3
    • MFCD00069342
    • (1s,2s,4as,13bs,14as)-methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride
    • methyl (1S,15S,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride
    • SMR000718802
    • Rauwolscine * HCl
    • MLS001306433
    • MLS001333079
    • MLS001333080
    • MLS002153884
    • SCHEMBL178033
    • SPECTRUM1503639
    • orb1302866
    • CHEMBL1257131
    • SCHEMBL29353997
    • DTXSID20977705
    • PIPZGJSEDRMUAW-ZKKXXTDSSA-N
    • HMS1569D16
    • Tox21_501093
    • CCG-40064
    • HY-12710A
    • s5337
    • AKOS016012193
    • CS-6984
    • EBC-616690
    • LP01093
    • NCGC00094366-01
    • NCGC00094366-02
    • NCGC00094366-03
    • NCGC00261778-01
    • DA-57354
    • FR145191
    • MS-26517
    • ST056351
    • EU-0101093
    • NS00081132
    • SR-01000597880
    • SR-01000075289-2
    • SR-01000597880-1
    • Isoyohimbine hydrochloride;corynanthidine hydrochloride
    • Q27286701
    • Methyl 17alpha-hydroxy-20alpha-yohimban-16beta-carboxylate--hydrogen chloride (1/1)
    • methyl (1S,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate hydrochloride
    • 6211-32-1

  • Applications

    Rauwolscine hydrochloride (CAS 6211-32-1) is an indole alkaloid and alpha-2 adrenergic receptor antagonist primarily used in pharmaceutical research; it also serves as a synthetic intermediate for preparing yohimbine-type alkaloids and related compounds, and is used in analytical laboratories as a reference standard and in receptor-binding studies; it is commonly used as a tool in medicinal chemistry to explore structure-activity relationships of adrenergic ligands.

    gpt-5-nano

  • Solubility @25˚C

    Solvent Solubility (g/L)
    ethanol 3.49
    methanol 22.65
    isopropanol 0.89
    water 4.37
    ethyl acetate 0.51
    n-propanol 1.43
    acetone 0.55
    n-butanol 1.74
    acetonitrile 0.25
    DMF 8.77
    toluene 0.05
    isobutanol 0.93
    1,4-dioxane 0.56
    methyl acetate 0.26
    THF 0.43
    2-butanone 0.42
    n-pentanol 1.4
    sec-butanol 0.41
    n-hexane 0.02
    ethylene glycol 10.77
    NMP 4.74
    cyclohexane 0.01
    DMSO 11.81
    n-butyl acetate 1.02
    n-octanol 1.01
    chloroform 1.51
    n-propyl acetate 0.7
    acetic acid 7.98
    dichloromethane 1.57
    cyclohexanone 1.37
    propylene glycol 1.48
    isopropyl acetate 0.52
    DMAc 8.62
    2-ethoxyethanol 8.28
    isopentanol 1.88
    n-heptane 0.03
    ethyl formate 1.68
    1,2-dichloroethane 0.75
    n-hexanol 1.31
    2-methoxyethanol 18.58
    isobutyl acetate 0.62
    tetrachloromethane 0.4
    n-pentyl acetate 2.27
    transcutol 20.87
    n-heptanol 2.27
    ethylbenzene 0.08
    MIBK 1.1
    2-propoxyethanol 9.93
    tert-butanol 0.58
    MTBE 0.08
    2-butoxyethanol 11.47
    propionic acid 1.56
    o-xylene 0.1
    formic acid 49.9
    diethyl ether 0.2
    m-xylene 0.14
    p-xylene 0.11
    chlorobenzene 0.15
    dimethyl carbonate 1.24
    n-octane 0.03
    formamide 39.53
    cyclopentanone 0.97
    2-pentanone 0.88
    anisole 0.22
    cyclopentyl methyl ether 0.26
    gamma-butyrolactone 1.5
    1-methoxy-2-propanol 7.55
    pyridine 0.44
    3-pentanone 0.45
    furfural 5.19
    n-dodecane 0.02
    diethylene glycol 25.93
    diisopropyl ether 0.1
    tert-amyl alcohol 0.41
    acetylacetone 1.5
    n-hexadecane 0.03
    acetophenone 0.92
    methyl propionate 0.69
    isopentyl acetate 1.24
    trichloroethylene 1.61
    n-nonanol 1.2
    cyclohexanol 0.45
    benzyl alcohol 1.17
    2-ethylhexanol 0.76
    isooctanol 1.84
    dipropyl ether 0.34
    1,2-dichlorobenzene 0.4
    ethyl lactate 2.63
    propylene carbonate 1.53
    n-methylformamide 7.96
    2-pentanol 0.53
    n-pentane 0.02
    1-propoxy-2-propanol 4.56
    1-methoxy-2-propyl acetate 2.3
    2-(2-methoxypropoxy) propanol 7.47
    mesitylene 0.13
    ε-caprolactone 1.56
    p-cymene 0.23
    epichlorohydrin 1.66
    1,1,1-trichloroethane 0.32
    2-aminoethanol 8.05
    morpholine-4-carbaldehyde 8.67
    sulfolane 4.55
    2,2,4-trimethylpentane 0.01
    2-methyltetrahydrofuran 0.16
    n-hexyl acetate 1.77
    isooctane 0.02
    2-(2-butoxyethoxy)ethanol 11.57
    sec-butyl acetate 0.41
    tert-butyl acetate 0.59
    decalin 0.02
    glycerin 13.65
    diglyme 14.52
    acrylic acid 2.8
    isopropyl myristate 0.57
    n-butyric acid 3.03
    acetyl acetate 0.73
    di(2-ethylhexyl) phthalate 2.42
    ethyl propionate 0.6
    nitromethane 5.83
    1,2-diethoxyethane 1.53
    benzonitrile 0.68
    trioctyl phosphate 1.71
    1-bromopropane 0.23
    gamma-valerolactone 5.81
    n-decanol 0.78
    triethyl phosphate 1.0
    4-methyl-2-pentanol 0.71
    propionitrile 0.38
    vinylene carbonate 2.34
    1,1,2-trichlorotrifluoroethane 12.79
    DMS 1.35
    cumene 0.14
    2-octanol 0.89
    2-hexanone 0.83
    octyl acetate 0.96
    limonene 0.23
    1,2-dimethoxyethane 4.82
    ethyl orthosilicate 0.87
    tributyl phosphate 1.63
    diacetone alcohol 2.8
    N,N-dimethylaniline 0.43
    acrylonitrile 0.84
    aniline 0.25
    1,3-propanediol 11.3
    bromobenzene 0.1
    dibromomethane 0.68
    1,1,2,2-tetrachloroethane 1.42
    2-methyl-cyclohexyl acetate 1.14
    tetrabutyl urea 2.73
    diisobutyl methanol 0.5
    2-phenylethanol 1.87
    styrene 0.07
    dioctyl adipate 1.36
    dimethyl sulfate 2.97
    ethyl butyrate 0.77
    methyl lactate 4.13
    butyl lactate 5.57
    diethyl carbonate 0.68
    propanediol butyl ether 9.79
    triethyl orthoformate 0.88
    p-tert-butyltoluene 0.19
    methyl 4-tert-butylbenzoate 3.58
    morpholine 0.88
    tert-butylamine 0.19
    n-dodecanol 0.5
    dimethoxymethane 4.4
    ethylene carbonate 1.64
    cyrene 7.56
    2-ethoxyethyl acetate 3.95
    2-ethylhexyl acetate 0.89
    1,2,4-trichlorobenzene 0.45
    4-methylpyridine 0.34
    dibutyl ether 0.38
    2,6-dimethyl-4-heptanol 0.5
    DEF 2.03
    dimethyl isosorbide 7.83
    tetrachloroethylene 2.05
    eugenol 7.45
    triacetin 2.8
    span 80 5.85
    1,4-butanediol 4.76
    1,1-dichloroethane 0.28
    2-methyl-1-pentanol 1.44
    methyl formate 4.77
    2-methyl-1-butanol 1.17
    n-decane 0.04
    butyronitrile 0.52
    3,7-dimethyl-1-octanol 0.94
    1-chlorooctane 0.2
    1-chlorotetradecane 0.09
    n-nonane 0.03
    undecane 0.03
    tert-butylcyclohexane 0.02
    cyclooctane 0.01
    cyclopentanol 0.35
    tetrahydropyran 0.16
    tert-amyl methyl ether 0.14
    2,5,8-trioxanonane 10.47
    1-hexene 0.08
    2-isopropoxyethanol 3.63
    2,2,2-trifluoroethanol 7.75
    methyl butyrate 1.01

    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