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Setiptiline

Synopsis, Chemistry

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Also known as: 57262-94-9, Org-8282, Setiptiline [inn], Org 8282, Mo 8282, 2,3,4,9-tetrahydro-2-methyl-1h-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine

Molecular Formula

C₁₉H₁₉N

Molecular Weight

261.4 g/mol

InChI Key

GVPIXRLYKVFFMK-UHFFFAOYSA-N

FDA UNII

7L38105Z6E

Setiptiline is a tetracyclic antidepressant (TeCA) which acts as a noradrenergic and specific serotonergic antidepressant (NaSSA). In Japan, the company Mochida started its commercialization for the treatment of depression started in 1989.

1 2D Structure

Setiptiline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methyl-4-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaene

2.1.2 InChI

InChI=1S/C19H19N/c1-20-11-10-18-16-8-4-2-6-14(16)12-15-7-3-5-9-17(15)19(18)13-20/h2-9H,10-13H2,1H3

2.1.3 InChI Key

GVPIXRLYKVFFMK-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCC2=C(C1)C3=CC=CC=C3CC4=CC=CC=C24

2.2 Other Identifiers

2.2.1 UNII

7L38105Z6E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,2,3,4-tetrahydro-2-methyl-9h-dibenzo(3,4-6,7)cyclohepta(1,2-c)pyridine

2. 13b,4a-carba-mianserin

3. Mo 8282

4. Mo-8282

5. Org 8282

6. Org-8282

2.3.2 Depositor-Supplied Synonyms

1. 57262-94-9

2. Org-8282

3. Setiptiline [inn]

4. Org 8282

5. Mo 8282

6. 2,3,4,9-tetrahydro-2-methyl-1h-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine

7. Setiptiline (inn)

8. 4-methyl-4-azatetracyclo[13.4.0.02,7.08,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaene

9. 7l38105z6e

10. Setiptilinum [latin]

11. Setiptilina [spanish]

12. Setiptilina

13. Setiptilinum

14. 2,3,4,9-tetrahydro-2-methyl-1h-dibenzo(3,4:6,7)cyclohepta(1,2-c)pyridine

15. 1h-dibenzo(3,4:6,7)cyclohepta(1,2-c)pyridine, 2,3,4,9-tetrahydro-2-methyl-

16. Einecs 260-653-4

17. Brn 1650422

18. Unii-7l38105z6e

19. 1h-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine, 2,3,4,9-tetrahydro-2-methyl-

20. Tecipul [as Maleate]

21. Setiptiline [mi]

22. Setiptiline [mart.]

23. Setiptiline [who-dd]

24. Schembl211362

25. Chembl2104895

26. Dtxsid50205886

27. Chebi:135076

28. Zinc1482169

29. Cs-1181

30. Db09304

31. Ncgc00378937-01

32. Ncgc00378937-02

33. Org 8282;org8282;org-8282

34. Hy-32329

35. Ft-0674569

36. D08511

37. 262s949

38. A923887

39. L003337

40. Q6590424

41. 1,2,3,4-tetrahydro-2-methyl-1h-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine

42. 2-methyl-2,3,4,9-tetrahydro-1h-dibenzo[3,4:6,7]cyclohepta[1,2-c]pyridine

43. 4-methyl-4-azatetracyclo[13.4.0.0^{2,7.0^{8,13]nonadeca-1(19),2(7),8,10,12,15,17-heptaene

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₁₉N
Molecular Weight	261.4 g/mol
XLogP3	3.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	0
Exact Mass	261.151749610 g/mol
Monoisotopic Mass	261.151749610 g/mol
Topological Polar Surface Area	3.2 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	397
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
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 depression.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Setiptiline is a tertacyclic antidepressant. It acts to reduce the symptoms of major depressive disorder.

5.2 Mechanism of Action

Setiptiline is an antagonist at the 2 adrenergic receptor and at serotonin receptors. The antagonism of the 2 receptors likely relieves presynaptic inhibition of adrenergic neurotransmission, allowing for greater and longer sustained release of noradrenaline into the synapse. The antagonism of serotonin receptors may produce an upregulation of the receptors leading to an eventual increase in serotonergic signalling. The actual physiological mechanisms behind the antidepressant effect of setiptiline is unknown but the listed possibilities exist as likely explanations.