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    Deserpidine

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 131-01-1, Harmonyl, Raunormine, Recanescin, Deserpidin, Recanescine
    Molecular Formula
    C32H38N2O8
    Molecular Weight
    578.7  g/mol
    InChI Key
    CVBMAZKKCSYWQR-WCGOZPBSSA-N
    FDA UNII
    9016E3VB47
    Deserpidine is an ester alkaloid derived from Rauwolfia canescens with antihypertensive activity. Deserpidine is a competitive inhibitor of the angiotensin converting enzyme (ACE). By competing with angiotensin I for ACE, deserpidine blocks the conversion of angiotensin I to angiotensin II, which is a potent vasoconstrictor. Reduced level of serum angiotensin II causes a decrease in blood pressure. Deserpidine also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex.
    Deserpidine is a Catecholamine-depleting Sympatholytic. The physiologic effect of deserpidine is by means of Decreased Sympathetic Activity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
    2.1.2 InChI
    InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
    2.1.3 InChI Key
    CVBMAZKKCSYWQR-WCGOZPBSSA-N
    2.1.4 Canonical SMILES
    COC1C(CC2CN3CCC4=C(C3CC2C1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
    2.1.5 Isomeric SMILES
    CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2[C@@H]1C(=O)OC)NC5=CC=CC=C45)OC(=O)C6=CC(=C(C(=C6)OC)OC)OC
    2.2 Other Identifiers
    2.2.1 UNII
    9016E3VB47
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. 131-01-1

    2. Harmonyl

    3. Raunormine

    4. Recanescin

    5. Deserpidin

    6. Recanescine

    7. Canescine

    8. Desepridine

    9. Raunormin

    10. Canescin

    11. Desmethoxyreserpine

    12. 11-demethoxyreserpine

    13. 11-desmethoxyreserpine

    14. Deserpidinum [inn-latin]

    15. Deserpidina [inn-spanish]

    16. Reserpidine

    17. Halmonyl

    18. Tranquinil

    19. Deresperine

    20. Deserpidine (inn)

    21. Chebi:27478

    22. Deserpidine, (-)-

    23. Deserpidic Acid, Methyl Ester, 3,4,5-trimethoxybenzoate

    24. Lilly 22641

    25. Nsc72138

    26. Nsc-72138

    27. Methyl (1r,15s,17r,18r,19s,20s)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

    28. Methyl (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate

    29. 9016e3vb47

    30. Ncgc00168786-01

    31. Ncgc00168786-02

    32. Deserpidina

    33. Deserpidinum

    34. Dsstox_cid_383

    35. Deserpidine [inn]

    36. Nsc 72138

    37. A-11025

    38. Deserpidine [inn:ban]

    39. Dsstox_rid_75556

    40. Dsstox_gsid_20383

    41. (3beta,16beta,17alpha,18beta,20alpha)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic Acid Methyl Ester

    42. Methyl (3beta,16beta,17alpha,18beta,20alpha)-17-(methyloxy)-18-({[3,4,5-tris(methyloxy)phenyl]carbonyl}oxy)yohimban-16-carboxylate

    43. Yohimban-16-carboxylic Acid,17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, Methyl Ester,(3b,16b,17a,18b,20a)-

    44. Halmonyl (tn)

    45. Cas-131-01-1

    46. Einecs 205-004-8

    47. Brn 0101820

    48. Unii-9016e3vb47

    49. Md-0232

    50. Methyl 17alpha-methoxy-18beta-(3,4,5-trimethoxybenzoyloxy)-3beta,20alpha-yohimban-16beta-carboxylat

    51. Methyl 18beta-hydroxy-17alpha-methoxy-3beta,20alpha-yohimban-16beta-carboxylate, 3,4,5-trimethoxybenzoate (ester)

    52. Deserpidine [mi]

    53. Deserpidine [vandf]

    54. Deserpidine [mart.]

    55. Deserpidine [who-dd]

    56. 3-beta,20-alpha-yohimban-16-beta-carboxylic Acid, 18-beta-hydroxy-17-alpha-methoxy-, Methyl Ester, 3,4,5-trimethoxybenzoate (ester)

    57. 4-25-00-01282 (beilstein Handbook Reference)

    58. Methyl 17alpha-methoxy-18beta-((3,4,5-trimethoxybenzoyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylate

    59. Mls006010113

    60. Schembl259343

    61. Gtpl7064

    62. Chembl1200515

    63. Dtxsid8020383

    64. Deserpidine [orange Book]

    65. Methyl 17.alpha.-methoxy-18.beta.-((3,4,5-trimethoxybenzoyl)oxy)-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate

    66. Methyl 18.beta.-hydroxy-17.alpha.-methoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate, 3,4,5-trimethoxybenzoate (ester)

    67. Zinc4097186

    68. Tox21_112646

    69. Tox21_113102

    70. Bdbm50480272

    71. Enduronyl Component Deserpidine

    72. Akos015896464

    73. Db01089

    74. Deserpidine Component Of Enduronyl

    75. (1s,2r,3r,4as,13br,14as)-methyl 2-methoxy-3-((3,4,5-trimethoxybenzoyl)oxy)-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate

    76. 17.alpha.-methoxy-18.beta.-[(3,4,5-trimethoxybenzoyl)oxy]-3.beta.,20.alpha.-yohimban-16.beta.-carboxylic Acid Methyl Ester

    77. Smr004701248

    78. Oreticyl Forte Component Deserpidine

    79. Hy-107339

    80. Cs-0028177

    81. Deserpidine Component Of Oreticyl Forte

    82. C06541

    83. D08194

    84. 131d011

    85. J-005923

    86. Q5263885

    87. Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,-13,13b,14,14a-dodecahydro-3-hydroxy-2-methoxy-, Methyl Ester, 3,4,5-trimethoxybenzoate

    88. Methyl (1r,15s,17r,18r,19s,20s)-18-methoxy-17-[(3,4,5-trimethoxyphenyl)carbonyloxy]-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate

    89. Yohimban-16-carboxylic Acid, 17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-, Methyl Ester, (3b,16b,17a,18b,20a)-

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 578.7 g/mol
    Molecular Formula C32H38N2O8
    XLogP34.1
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count9
    Exact Mass578.26281617 g/mol
    Monoisotopic Mass578.26281617 g/mol
    Topological Polar Surface Area109 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity953
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of hypertension.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Deserpidine, an alkaloid of Rauwolfia canescens, is used as an antihypertensive. Rauwolfia alkaloids work by controlling nerve impulses along certain nerve pathways. As a result, they act on the heart and blood vessels to lower blood pressure.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    DESERPIDINE
    5.2.2 FDA UNII
    9016E3VB47
    5.2.3 Pharmacological Classes
    Physiologic Effects [PE] - Decreased Sympathetic Activity
    5.3 ATC Code

    C - Cardiovascular system

    C02 - Antihypertensives

    C02A - Antiadrenergic agents, centrally acting

    C02AA - Rauwolfia alkaloids

    C02AA05 - Deserpidine

    5.4 Mechanism of Action

    Deserpidine's mechanism of action is through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.