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2D Structure
Also known as: 135354-02-8, Sr 57746, Xaliproden (usan), V8ql94knqo, Pyridine, 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-, Chebi:48520
Molecular Formula
C24H22F3N
Molecular Weight
381.4  g/mol
InChI Key
WJJYZXPHLSLMGE-UHFFFAOYSA-N
FDA UNII
V8QL94KNQO

1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2H-pyridine
2.1.2 InChI
InChI=1S/C24H22F3N/c25-24(26,27)23-7-3-6-22(17-23)20-11-14-28(15-12-20)13-10-18-8-9-19-4-1-2-5-21(19)16-18/h1-9,11,16-17H,10,12-15H2
2.1.3 InChI Key
WJJYZXPHLSLMGE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CN(CC=C1C2=CC(=CC=C2)C(F)(F)F)CCC3=CC4=CC=CC=C4C=C3
2.2 Other Identifiers
2.2.1 UNII
V8QL94KNQO
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(2-(naphth-2-yl)ethyl)-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine Hydrochloride

2. 1-(2-(naphth-2-yl)ethyl)-4-(trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine Hydrochloride

3. Sr 57746a

4. Sr-57746a

5. Sr57746a

6. Xaliproden Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 135354-02-8

2. Sr 57746

3. Xaliproden (usan)

4. V8ql94knqo

5. Pyridine, 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-

6. Chebi:48520

7. 1,2,3,6-tetrahydro-1-(2-(2-naphthyl)ethyl)-4-(alpha,alpha,alpha-trifluoro-m-tolyl)pyridine

8. Sr-57746

9. Xaliproden [usan]

10. 1,2,3,6-tetrahydro-1-(2-(2-naphthalenyl)ethyl)-4-(3-(trifluoromethyl)phenyl)-pyridine

11. 1-(2-(2-naphthyl)ethyl)-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

12. 1-[2-(2-naphthyl)ethyl]-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

13. Ncgc00167574-01

14. Unii-v8ql94knqo

15. Xaliproden [usan:inn:ban]

16. 1-[2-(2-naphthyl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

17. Xaliproden [mi]

18. Xaliproden [inn]

19. 1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-3,6-dihydro-2h-pyridine

20. Xaliproden [who-dd]

21. Schembl137094

22. Chembl1512580

23. Dtxsid9048306

24. Bdbm82363

25. Zinc577115

26. Pdsp1_000054

27. Pdsp2_000054

28. Db06393

29. Sr 57746 A

30. Ncgc00167574-02

31. Cas_90494-79-4

32. Db-063077

33. Ft-0736660

34. D06327

35. L001401

36. Brd-k88358234-003-01-4

37. Q12745720

38. 1-(2-naphthalen-2-ylethyl)-4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine

39. 1-[2(naphth-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,5,6-tetrahydropyridine

40. 1-[2-(naphth-2-yl)ethyl]-4-(3-trifluoromethylphenyl)-1,2,3,6-tetrahydropyridine

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 381.4 g/mol
Molecular Formula C24H22F3N
XLogP36.2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass381.17043419 g/mol
Monoisotopic Mass381.17043419 g/mol
Topological Polar Surface Area3.2 Ų
Heavy Atom Count28
Formal Charge0
Complexity541
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in amyotrophic lateral sclerosis (ALS) and alzheimer's disease.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Serotonin 5-HT1 Receptor Agonists

Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)


5.2 ATC Code

N - Nervous system

N07 - Other nervous system drugs

N07X - Other nervous system drugs

N07XX - Other nervous system drugs

N07XX03 - Xaliproden


5.3 Mechanism of Action

Xaliproden is an orally-active, synthetic, non-peptidic 5-hydroxytryptamine (5-HT) 1A receptor agonist with neurotrophic and neuroprotective activities. Although its mechanism of action is not fully understood, xaliproden appears to either mimic the effects of neurotrophins or stimulate their synthesis, thereby stimulating neuronal cell differentiation and proliferation and inhibiting neuronal cell death. The neuroprotective effect of this agent involves the activation of MAP kinase pathways via stimulation of the 5-HT1A receptor.