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Boldine

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ACTIVE PHARMA INGREDIENTS

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Synopsis

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Chemistry

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Also known as: 476-70-0, Uniboldina, Boldin, (s)-boldine, Boldine chloroform, 1,10-dimethoxy-2,9-dihydroxyaporphine

Molecular Formula

C₁₉H₂₁NO₄

Molecular Weight

327.4 g/mol

InChI Key

LZJRNLRASBVRRX-ZDUSSCGKSA-N

FDA UNII

8I91GE2769

(9S)-4,16-dimethoxy-10-methyl-10-azatetracyclo[7.7.1.0,.0,]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-5,15-diol is a natural product found in Lindera umbellata, Damburneya salicifolia, and other organisms with data available.

1 2D Structure

Boldine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6aS)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-2,9-diol

2.1.2 InChI

InChI=1S/C19H21NO4/c1-20-5-4-10-7-15(22)19(24-3)18-12-9-16(23-2)14(21)8-11(12)6-13(20)17(10)18/h7-9,13,21-22H,4-6H2,1-3H3/t13-/m0/s1

2.1.3 InChI Key

LZJRNLRASBVRRX-ZDUSSCGKSA-N

2.1.4 Canonical SMILES

CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)O

2.1.5 Isomeric SMILES

CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)O

2.2 Other Identifiers

2.2.1 UNII

8I91GE2769

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 476-70-0

2. Uniboldina

3. Boldin

4. (s)-boldine

5. Boldine Chloroform

6. 1,10-dimethoxy-2,9-dihydroxyaporphine

7. (+)-boldine

8. Nsc 65689

9. 2,9-dihydroxy-1,10-dimethoxyaporphine

10. (s)-(+)-boldine

11. 1,10-dimethoxy-6a-alpha-aporphine-2,9-diol

12. (6as)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,9-diol

13. Chebi:3148

14. Chembl388342

15. 4h-dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6as)-

16. 8i91ge2769

17. (s)-1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,9-diol

18. 4h-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (6as)-

19. 4h-dibenzo(de,g)quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (s)-

20. (+)-(s)-boldine

21. Einecs 207-509-9

22. Brn 0094036

23. Nsc-65689

24. Ex Peumus Boldus

25. Unii-8i91ge2769

26. Aprophine Alkaloid

27. 4h-dibenzo[de,g]quinoline-2,9-diol, 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-, (s)-

28. Prestwick_46

29. Boldine [mi]

30. Prestwick3_000600

31. Boldine [who-dd]

32. 6aalpha-aporphine-2,9-diol, 1,10-dimethoxy-

33. Boldine, Analytical Standard

34. Bspbio_000480

35. 5-21-06-00118 (beilstein Handbook Reference)

36. Cid_10154

37. Mls002153899

38. Schembl177550

39. Boldine [ep Monograph]

40. 6a-alpha-aporphine-2,9-diol, 1,10-dimethoxy-

41. Bpbio1_000528

42. Cid_248507

43. Dtxsid40883394

44. 5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-4h-dibenzo[de,g]quinoline-2,9-diol

45. Hms2096h22

46. Hms2235b04

47. Zinc135449

48. Hy-n6973

49. Tnp00245

50. Bdbm50202318

51. Mfcd00135040

52. S9050

53. Zb1855

54. Boldine, Analytical Reference Material

55. 2,6-dihydroxy-3,5-dimethoxyaporphine

56. Akos015912953

57. Ccg-208461

58. Ncgc00016454-01

59. Ncgc00016454-02

60. Ncgc00017314-01

61. Ncgc00179547-01

62. Ac-34043

63. As-17759

64. Cas-476-70-0

65. Smr001233248

66. Cs-0013445

67. C09365

68. 1,10-dimethoxy-6a-.alpha.-aporphine-2,9-diol

69. 476b700

70. 6a.alpha.-aporphine-2,9-diol, 1,10-dimethoxy-

71. A872092

72. Q2070105

73. 1,10-dimethoxy-6a.alpha.-aporphine-2,9-diol

74. Brd-k03440695-001-02-6

75. Boldine, European Pharmacopoeia (ep) Reference Standard

76. 1,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-2,9-diol, (s)-

77. (6as)-5,6,6a,7-tetrahydro-1,10-dimethoxy-6-methyl-4h-dibenzo(de,g)quinoline-2,9-diol

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₁NO₄
Molecular Weight	327.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	327.14705815 g/mol
Monoisotopic Mass	327.14705815 g/mol
Topological Polar Surface Area	62.2 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	461
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Neuromuscular Depolarizing Agents

Drugs that interrupt transmission at the skeletal neuromuscular junction by causing sustained depolarization of the motor end plate. These agents are primarily used as adjuvants in surgical anesthesia to cause skeletal muscle relaxation. (See all compounds classified as Neuromuscular Depolarizing Agents.)

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