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2D Structure
Also known as: Evp-6124, 550999-75-2, Evp 6124, Evp6124, N-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide, Chembl2151572
Molecular Formula
C16H17ClN2OS
Molecular Weight
320.8  g/mol
InChI Key
SSRDSYXGYPJKRR-ZDUSSCGKSA-N
FDA UNII
5FI5376A0X

Encenicline has been investigated for the treatment of Cognition, Schizophrenia, Alzheimer's Disease, Cardiac Repolarization, and Central Nervous System Diseases.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide
2.1.2 InChI
InChI=1S/C16H17ClN2OS/c17-12-3-1-2-11-8-14(21-15(11)12)16(20)18-13-9-19-6-4-10(13)5-7-19/h1-3,8,10,13H,4-7,9H2,(H,18,20)/t13-/m0/s1
2.1.3 InChI Key
SSRDSYXGYPJKRR-ZDUSSCGKSA-N
2.1.4 Canonical SMILES
C1CN2CCC1C(C2)NC(=O)C3=CC4=C(S3)C(=CC=C4)Cl
2.1.5 Isomeric SMILES
C1CN2CCC1[C@H](C2)NC(=O)C3=CC4=C(S3)C(=CC=C4)Cl
2.2 Other Identifiers
2.2.1 UNII
5FI5376A0X
2.3 Synonyms
2.3.1 MeSH Synonyms

1. N-(7-chloro-n-quinuclidin-3-yl)benzo(b)thiophene-2-carboxamide

2.3.2 Depositor-Supplied Synonyms

1. Evp-6124

2. 550999-75-2

3. Evp 6124

4. Evp6124

5. N-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-chloro-1-benzothiophene-2-carboxamide

6. Chembl2151572

7. 5fi5376a0x

8. Mt4666

9. Mt-4666

10. Benzo(b)thiophene-2-carboxamide, N-(3r)-1-azabicyclo(2.2.2)oct-3-yl-7-chloro-

11. (r)-7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide

12. 7-chloro-n-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide

13. Unii-5fi5376a0x

14. Encenicline [usan:inn]

15. Frm-6124

16. I33

17. Encenicline [inn]

18. Encenicline (usan/inn)

19. Encenicline [usan]

20. Encenicline [who-dd]

21. Schembl744767

22. Gtpl6926

23. (r)-7-chloro-n-(quinuclidin-3-yl)benzo(b)thiophene-2-carboxamide

24. Dtxsid701025836

25. Ex-a3984

26. Bdbm50393255

27. Mfcd23381267

28. Zinc95579362

29. Cs-0933

30. Db11726

31. Ncgc00378871-01

32. Hy-15430

33. D10626

34. A913801

35. Q19904062

36. (r)-7-chloro-n-(quinuclidine-3-yl)benzo[b]thiophene-2-carboxamide

37. N-((3r)-1-azabicyclo(2.2.2)oct-3-yl)-7-chloro-1-benzothiophene-2-carboxamide

38. N-(3r)-1-azabicyclo[2.2.2]oct-3-yl-7-chlorobenzo[b]thiophene-2-carboxamide

39. 1275596-71-8

2.4 Create Date
2010-07-06
3 Chemical and Physical Properties
Molecular Weight 320.8 g/mol
Molecular Formula C16H17ClN2OS
XLogP33.8
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Exact Mass320.0750120 g/mol
Monoisotopic Mass320.0750120 g/mol
Topological Polar Surface Area60.6 Ų
Heavy Atom Count21
Formal Charge0
Complexity413
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Mechanism of Action

Encenicline, a selective, orally active, alpha 7 Nicotinic Acetylcholine Receptor agonist (alpha 7 NAchR agonist). Encenicline may have a similar mechanism of action to GTS-21. Auditory sensory gating, a biological measurement of the ability to suppress the evoked response to the second of two auditory stimuli, is diminished in people with schizophrenia. Deficits in sensory gating are associated with attentional impairment, and may contribute to cognitive symptoms and perceptual disturbances. This inhibitory process, which involves the alpha(7) nicotinic receptor mediated release of gamma-aminobutyric acid (GABA) by hippocampal interneurons, represents a potential new target for therapeutic intervention in schizophrenia.