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Chemistry

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Also known as: Rotundine, 483-14-7, L-tetrahydropalmatine, (-)-tetrahydropalmatine, Gindarine, Caseanine

Molecular Formula

C₂₁H₂₅NO₄

Molecular Weight

355.4 g/mol

InChI Key

AEQDJSLRWYMAQI-KRWDZBQOSA-N

FDA UNII

3X69CO5I79

tetrahydropalmatine is a natural product found in Corydalis heterocarpa, Ceratocapnos heterocarpa, and other organisms with data available.

1 2D Structure

Rotundine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(13aS)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline

2.1.2 InChI

InChI=1S/C21H25NO4/c1-23-18-6-5-13-9-17-15-11-20(25-3)19(24-2)10-14(15)7-8-22(17)12-16(13)21(18)26-4/h5-6,10-11,17H,7-9,12H2,1-4H3/t17-/m0/s1

2.1.3 InChI Key

AEQDJSLRWYMAQI-KRWDZBQOSA-N

2.1.4 Canonical SMILES

COC1=C(C2=C(CC3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC

2.1.5 Isomeric SMILES

COC1=C(C2=C(C[C@H]3C4=CC(=C(C=C4CCN3C2)OC)OC)C=C1)OC

2.2 Other Identifiers

2.2.1 UNII

3X69CO5I79

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+-)-isomer Of Tetrahydropalmatine

2. (r)-isomer; Corydalis B Of Tetrahydropalmatine

3. (s)-isomer Of Tetrahydropalmatine

4. 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6h-dibenzo(a,g)quinolizine

5. Corydalis B

6. Gindarin

7. Hcl Of Tetrahydropalmatine

8. Hcl(+-)-isomer Of Tetrahydropalmatine

9. Hcl(r)-isomer Of Tetrahydropalmatine

10. Hcl(s)-isomer Of Tetrahydropalmatine

11. Levo-tetrahydropalmatine

12. Rotundine

13. Rotundium

14. Tetrahydropalmitine

2.3.2 Depositor-Supplied Synonyms

1. Rotundine

2. 483-14-7

3. L-tetrahydropalmatine

4. (-)-tetrahydropalmatine

5. Gindarine

6. Caseanine

7. Hyndarine

8. (s)-tetrahydropalmatine

9. (-)-corydalis B

10. (-)-rotundine

11. (s)-(-)-tetrahydropalmatine

12. (13as)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[2,1-b]isoquinoline

13. Tetrahydropalmatine, L-

14. (s)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[3,2-a]isoquinoline

15. Tetrahydropalmatine, (-)-

16. Chebi:16563

17. 3x69co5i79

18. 2,3,9,10-tetramethoxy-13aalpha-berbine

19. Hyndarin

20. (-)-corydalis

21. (13as)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6h-isoquino[3,2-a]isoquinoline

22. Tetrahydropalmatine, Dl-

23. Nsc36363

24. 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6h-dibenzo(a,g)quinolizine

25. Berbine, 2,3,9,10-tetramethoxy-

26. (-)-s-tetrahydropalmatine

27. Unii-3x69co5i79

28. 2,3,9,10-tetramethoxyberbine

29. 13a-alpha-berbine, 2,3,9,10-tetramethoxy-

30. (-)-2,3,9,10-tetramethoxyberbine

31. Tetrahydropalmatine L-form

32. (s)-5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-6h-dibenzo(a,g)quinolizine

33. 6h-dibenzo(a,g)quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (s)-

34. Schembl230850

35. Chembl487182

36. Dtxsid701020650

37. Hms3656m19

38. Hms3884j17

39. Hy-n0096

40. Tetrahydropalmatine [who-dd]

41. Bdbm50424077

42. Mfcd03265591

43. S2437

44. Zinc19535049

45. Akos000277105

46. Ac-8007

47. Ccg-268100

48. Cs-8092

49. Db12093

50. Tetrahydropalmatine L-form [mi]

51. 6h-dibenzo[a,g]quinolizine, 5,8,13,13a-tetrahydro-2,3,9,10-tetramethoxy-, (13as)-

52. Ncgc00346591-01

53. Ac-16039

54. As-17459

55. As-82762

56. (-)-tetrahydropalmatine, >=98% (hplc)

57. N1727

58. Sw219613-1

59. T3311

60. C02890

61. 483t147

62. A913918

63. Q-100022

64. Q-100371

65. Q7706555

66. (13as)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6h-dibenzo[a,g]quinolizine

67. (13as)-2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5h-isoquinolino[3,2-a]isoquinoline

68. (s)-2,3,9,10-tetramethoxy-5,8,13,13a-tetrahydro-6h-isoquinolino[3,2-a]isoquinoline

69. 2-(2,3-dimethoxy-benzyl)-1-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline

70. 5,8,13,13a(s)-tetrahydro-2,3,9,10-tetramethoxy-6h-dibenzo[a,g]quinolizine

71. 5,8,13,13a-tetrahydro-(s)-2,3,9,10-tetramethoxy-6h-dibenzo(a,g)quinolizine

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₅NO₄
Molecular Weight	355.4 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	355.17835828 g/mol
Monoisotopic Mass	355.17835828 g/mol
Topological Polar Surface Area	40.2 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	475
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

Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)

Calcium Channel Blockers

A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

Adrenergic Agents

Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters. (See all compounds classified as Adrenergic Agents.)

Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

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