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Chemistry

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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

Deserpidine

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 Formula	C₃₂H₃₈N₂O₈
Molecular Weight	578.7 g/mol
XLogP3	4.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	9
Exact Mass	578.26281617 g/mol
Monoisotopic Mass	578.26281617 g/mol
Topological Polar Surface Area	109 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	953
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.

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