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    Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16alpha,17alpha)-

    ACTIVE PHARMA INGREDIENTS

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    2D Structure
    Also known as: 65-19-0, Yohimbine hcl, Antagonil, Yohimbe, Aphrodine hydrochloride, Yohimbine monohydrochloride
    Molecular Formula
    C21H27ClN2O3
    Molecular Weight
    390.9  g/mol
    InChI Key
    PIPZGJSEDRMUAW-VJDCAHTMSA-N
    FDA UNII
    NB2E1YP49F
    A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride
    2.1.2 InChI
    InChI=1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H/t12-,15-,17-,18-,19+;/m0./s1
    2.1.3 InChI Key
    PIPZGJSEDRMUAW-VJDCAHTMSA-N
    2.1.4 Canonical SMILES
    COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
    2.1.5 Isomeric 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
    2.2 Other Identifiers
    2.2.1 UNII
    NB2E1YP49F
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aphrodine Hydrochloride

    2. Aphrodyne

    3. Corynanthine

    4. Corynanthine Tartrate

    5. Hydrochloride, Aphrodine

    6. Hydrochloride, Yohimbine

    7. Pluriviron

    8. Rauhimbine

    9. Rauwolscine

    10. Tartrate, Corynanthine

    11. Yocon

    12. Yohimbin Spiegel

    13. Yohimbine

    14. Yohimbine Houd

    15. Yohimex

    2.3.2 Depositor-Supplied Synonyms

    1. 65-19-0

    2. Yohimbine Hcl

    3. Antagonil

    4. Yohimbe

    5. Aphrodine Hydrochloride

    6. Yohimbine Monohydrochloride

    7. Yohimbine (hydrochloride)

    8. Nb2e1yp49f

    9. Actibine

    10. Mfcd00012674

    11. 17-hydroxyyohimban-16-carboxylic Acid Methyl Ester Hydrochloride

    12. Yohimbine Chloride

    13. Nsc-19509

    14. Yohimbin Hcl

    15. Chembl537669

    16. Methyl (1s,15r,18s,19r,20s)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

    17. 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 Hydrochloride

    18. Smr000058527

    19. Yohimbin Hydrochloride [usp]

    20. Yohimbin Hydrochloride

    21. Sr-01000597896

    22. Einecs 200-600-4

    23. Nsc 19509

    24. Unii-nb2e1yp49f

    25. Parkimbine

    26. Aphrodyne

    27. Gynimbine

    28. Menolysin

    29. Thybine

    30. Tosanpin

    31. Yobinol

    32. Yohydrol

    33. Yocon

    34. Ai3-60247

    35. Dayto-himbin

    36. Sr-01000075297

    37. Yohimbine, Hcl

    38. Yohimbine Hydrochloride [usp:ban]

    39. Prestwick_961

    40. Nsc19509

    41. Yohimbine-hydrochloride

    42. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, Monohydrochloride, (16alpha,17alpha)-

    43. Mls001306411

    44. Mls001333983

    45. Yohimbine Hydrochloride (usp)

    46. Dtxsid40891272

    47. Hms1569f10

    48. Yohimbine Hydrochloride (antagonil)

    49. (1r,2s,4ar,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

    50. Bcp19708

    51. Hy-n0127

    52. Nih 9689

    53. Tox21_501210

    54. Yohimbine Hydrochloride [mi]

    55. S2373

    56. Akos015951349

    57. Ccg-208327

    58. Cs-5238

    59. Lp01210

    60. Yohimbine Hydrochloride [mart.]

    61. Yohimbine Hydrochloride [vandf]

    62. 17alpha-hydroxy-20-alpha-yohimban-16-beta-carboxylic Acid, Methyl Ester, Hydrochloride

    63. Yohimban-16-alpha-carboxylic Acid, 17-alpha-hydroxy-, Methyl Ester, Hydrochloride

    64. Yohimban-16alpha-carboxylic Acid, 17alpha-hydroxy-, Methyl Ester, Monohydrochloride

    65. Yohimbine Hydrochloride [usp-rs]

    66. Yohimbine Hydrochloride [who-dd]

    67. Ncgc00094457-01

    68. Ncgc00261895-01

    69. Ac-22571

    70. As-13939

    71. Yohimbine Hydrochloride [green Book]

    72. Yohimbine Hydrochloride, Analytical Standard

    73. Eu-0101210

    74. N1704

    75. Sw199050-2

    76. Y0002

    77. Yohimbine Hydrochloride [ep Monograph]

    78. D06671

    79. Y 3125

    80. Yohimbine Hydrochloride [usp Monograph]

    81. Yohimbine Hydrochloride, >=98% (tlc), Powder

    82. 012y674

    83. Q-201938

    84. Sr-01000075297-1

    85. Sr-01000597896-1

    86. Sr-01000597896-4

    87. Q15680050

    88. 17?-hydroxyyohimban-16?-carboxylic Acid Methyl Ester Hydrochloride

    89. Yohimbine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    90. Yohimbine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    91. 17.alpha.-hydroxy-20-.alpha.-yohimban-16-.beta.-carboxylic Acid, Methyl Ester, Hydrochloride

    92. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, Hydrochloride (1:1), (16alpha,17alpha)-

    2.4 Create Date
    2005-07-19
    3 Chemical and Physical Properties
    Molecular Weight 390.9 g/mol
    Molecular Formula C21H27ClN2O3
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass390.1710204 g/mol
    Monoisotopic Mass390.1710204 g/mol
    Topological Polar Surface Area65.6 Ų
    Heavy Atom Count27
    Formal Charge0
    Complexity555
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Urological Agents

    Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)

    Adrenergic alpha-2 Receptor Antagonists

    Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)

    Mydriatics

    Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)