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Ajmalicin

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Synopsis

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Chemistry

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Also known as: Raubasine, 483-04-5, Delta-yohimbine, Ajmalicin, Circolene, Tetrahydroserpentine

Molecular Formula

C₂₁H₂₄N₂O₃

Molecular Weight

352.4 g/mol

InChI Key

GRTOGORTSDXSFK-XJTZBENFSA-N

FDA UNII

4QJL8OX71Z

substance II is a natural product found in Crossosoma bigelovii, Rauvolfia yunnanensis, and other organisms with data available.

1 2D Structure

Ajmalicin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (1S,15R,16S,20S)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

2.1.2 InChI

InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16+,19-/m0/s1

2.1.3 InChI Key

GRTOGORTSDXSFK-XJTZBENFSA-N

2.1.4 Canonical SMILES

CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45

2.1.5 Isomeric SMILES

C[C@H]1[C@H]2CN3CCC4=C([C@@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

2.2 Other Identifiers

2.2.1 UNII

4QJL8OX71Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 19-epiajmalicine

2. Ajmalicine Hydrochloride

3. Ajmalicine, (19alpha,20alpha)-isomer

4. Ajmalicine, (19beta)-isomer

5. Ajmalicine, (19beta,20alpha)-isomer

6. Ajmalicine, (3-beta,19beta)-isomer

7. Ajmalicine, (3beta,19alpha)-isomer

8. Ajmalicine, (3beta,19alpha,20alpha)-isomer

9. Ajmalicine, (hydrochloride(19beta,20alpha))-isomer

10. Ajmalicine, Hydrochloride(19alpha)-isomer

11. Ajmalicine, Po4(19alpha)-isomer

12. Akuammigine

13. Delta-yohimbine

14. Lamuran

15. Raubasine

16. Raubasine Hcl

17. Raubasine Hydrochloride

18. Rauvasan

19. Tetrahydro-alstonine

20. Tetrahydroalstonine

2.3.2 Depositor-Supplied Synonyms

1. Raubasine

2. 483-04-5

3. Delta-yohimbine

4. Ajmalicin

5. Circolene

6. Tetrahydroserpentine

7. Lamuran

8. Rauvasan

9. Hydrosarpan

10. Sarpan

11. Alkaloid C

12. Substance Ii

13. Py-tetrahydroserpentine

14. Rauwolfia Serpentina Root

15. 4qjl8ox71z

16. Chebi:2524

17. Chembl123325

18. .delta.-yohimbine

19. Nsc 72133

20. Methyl (19alpha)-19-methyl-16,17-didehydro-18-oxayohimban-16-carboxylate

21. Isoarteril

22. Methyl (1s,15r,16s,20s)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

23. 16,17-didehydro-19-methyloxayohimban-16-carboxylic Acid Methyl Ester

24. Ajmalicine(-yohimbine)

25. Einecs 207-589-5

26. Unii-4qjl8ox71z

27. Brn 0097268

28. Cristanyl

29. Del.-yohimbine

30. Nsc-72133

31. Rauwolfia Alkaloid

32. Raubasine,(s)

33. Raubasine (dcf)

34. Lamuran (tn)

35. Spectrum_000775

36. Specplus_000425

37. Raubasine [mi]

38. Prestwick0_000592

39. Prestwick1_000592

40. Prestwick2_000592

41. Prestwick3_000592

42. Methyl 16,17-didehydro-19alpha-methyl-18-oxayohimban-16-carboxylat

43. Raubasine [mart.]

44. Pytetrahydroserpentine

45. Raubasine [who-dd]

46. Methyl (19-methyl-16,17-dehydro-18-oxa-3alpha,15alpha,19beta,20beta-yohimban-16-carboxylat)

47. Bspbio_000464

48. Kbioss_001255

49. 4-27-00-07927 (beilstein Handbook Reference)

50. Divk1c_006521

51. Schembl309914

52. Spbio_002683

53. Bpbio1_000512

54. Gtpl8746

55. Megxp0_001818

56. Acon1_001630

57. Kbio1_001465

58. Kbio2_001255

59. Kbio2_003823

60. Kbio2_006391

61. Dtxsid60904151

62. Hy-n1919

63. Bdbm50030612

64. Mfcd00042748

65. Zinc53147422

66. Akos015895125

67. Oxayohimban-16-carboxylic Acid, 16,17-didehydro-19-methyl-, Methyl Ester, (19-alpha)-

68. Ncgc00016647-01

69. Ncgc00016647-02

70. Ncgc00016647-03

71. Ncgc00016647-04

72. Ac-20175

73. As-35306

74. Cas-4373-34-6

75. Cas-6474-90-4

76. (4s,4ar,13bs,14as)-methyl 4-methyl-

77. Cs-0018230

78. C09024

79. D08470

80. [2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate

81. 483a045

82. Q412957

83. 4a,5,7,8,13,13b,14,14a-octahydro-4h-indolo

84. W-106052

85. Brd-k83028735-001-01-6

86. Brd-k83028735-003-03-8

87. 19b-methyl-16-methoxycarbonyl-16,17-didehydro-oxayohimbane

88. Methyl (19alpha)-19-methyl-16,17-didehydrooxayohimban-16-carboxylate

89. (19.alpha.)-16,17-didehydro-19-methyloxayohimban-16-carboxylic Acid Methyl Ester

90. (19alpha)-16,17-didehydro-19-methyl-oxayohimban-16-carboxylic Acid Methyl Ester

91. Oxayohimban-16-carboxylic Acid, 16,17-didehydro-19-methyl-, Methyl Ester, (19-.alpha).-

92. Oxayohimban-16-carboxylic Acid, 16,17-didehydro-19-methyl-, Methylester, (19a)-

93. Oxayohimban-16-carboxylicacid, 16,17-didehydro-19-methyl-, Methyl Ester, (19a)-

94. (4s,4ar,13bs,14as)-methyl 4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4h-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate

95. (7ar,8s,11as,12as)-8-methyl-5,6,7a,8,11a,12,12a,13-octahydro-7h-9-oxa-6a,13-diaza-indeno[2,1-a]anthracene-11-carboxylic Acid Methyl Ester

96. Ajn

97. Methyl (1s,15r,16s,20s)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-2(10),4,6,8,18-pentaene-19-carboxylate

98. Methyl (4s,4ar,13bs,14as)-4-methyl-4a,5,7,8,13,13b,14,14a-octahydro-4h-indolo[2,3-a]pyrano[3,4-g]quinolizine-1-carboxylate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₄N₂O₃
Molecular Weight	352.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	352.17869263 g/mol
Monoisotopic Mass	352.17869263 g/mol
Topological Polar Surface Area	54.6 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	606
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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

Rauwolfia alkaloids are indicated in the treatment of hypertension. Rauwolfia alkaloids have been used for relief of symptoms in agitated psychotic states such as schizophrenia; however, use as antipsychotics and sedatives have been replaced with the use of more effective, safer agents.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Reserpine is used to treat high blood pressure. It also is used to treat severe agitation in patients with mental disorders. Reserpine is in a class of medications called rauwolfia alkaloids. It works by slowing the activity of the nervous system, causing the heart rate to slow and the blood vessels to dilate.

5.2 MeSH Pharmacological Classification

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.3 Absorption, Distribution and Excretion

Absorption

Mean maximum plasma levels of plasma concentrations after 0.5 mg of Reserpine, administered as two 0.25 mg tablets or as an aqueous solution, peaked after 2.5 hours. The mean peak level was approximately 1.1 ng/ml. Bioavailability of Reserpine, has been reported to be approximately 50%.

Route of Elimination

The elimination of reserpine and its metabolites in the feces ranges from 30% after intramuscular administration to about 60% after oral ingestion, primarily as unmetabolized reserpine, over a 4 day period after the ingestionof 0.25 mg to 0.50 mg doses. Over the same time period, about 8% of the ingested dose was recovered in the urine, primarily as the trimethoxybenzoic acid metabolite.

Clearance

Hepatically and renally.

5.4 Metabolism/Metabolites

Reserpine is almost completely metabolized in the body, and only about 1% is excreted as unchanged drug in the urine. Hepatic metabolism accounts for less than 50% of the elimination of reserpine, with the remainder being eliminated in the faeces, and some unmetabolized reserpine and metabolites being eliminated in the urine. In man, metabolites are methylreserpate and trimethoxybenzoic acid. Metabolism may be more important with intramuscular administration.

5.5 Biological Half-Life

After oral ingestion, an initial half-life of approximately 5 hours is followed by a terminal half-life of approximately 200 hours.

5.6 Mechanism of Action

Reserpine is an adrenergic blocking agent used to treat mild to moderate hypertension via the disruption of norepinephrine vesicular storage. The antihypertensive actions of Reserpine are a result of its ability to deplete catecholamines from peripheral sympathetic nerve endings. These substances are normally involved in controlling heart rate, the work of cardiac contraction and peripheral resistance. Reserpine depletes brain (depression) and peripheral (PPH) noradrenaline (NA) storage sites, guanethidine depleted NA storage via blockade of reuptake. This agent binds and inhibits catecholamine pump on the storage vesicles in central and peripheral adrenergic neurons, thereby inhibiting the uptake of norepinephrine, dopamine serotonin into presynaptic storage vesicles. This results in catecholamines and serotonin lingering in the cytoplasm where they are destroyed by intraneuronal monoamine oxidase, thereby causing the depletion of catecholamine and serotonin stores in central and peripheral nerve terminals. Depletion results in a lack of active transmitter discharge from nerve endings upon nerve depolarization, and consequently leads to a decreased heart rate and decreased arterial blood pressure as well as sedative effects.

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