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Dasotraline

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Chemistry

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Also known as: 675126-05-3, (1r,4s)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine, (1r,4s)-trans-norsertraline, Norsertraline, (1r,4s)-trans-, Sep-225289, 4d28ey0l5t

Molecular Formula

C₁₆H₁₅Cl₂N

Molecular Weight

292.2 g/mol

InChI Key

SRPXSILJHWNFMK-MEDUHNTESA-N

FDA UNII

4D28EY0L5T

Dasotraline is a serotonin, norepinephrine and dopamine reuptake inhibitor (SNDRI) that is under investigation for the treatment of Binge Eating Disorder, Adult Attention Hyperactivity Disorder, Attention Deficit Hyperactivity Disorder, and Adult Attention Deficit Hyperactivity Disorder.

1 2D Structure

Dasotraline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine

2.1.2 InChI

InChI=1S/C16H15Cl2N/c17-14-7-5-10(9-15(14)18)11-6-8-16(19)13-4-2-1-3-12(11)13/h1-5,7,9,11,16H,6,8,19H2/t11-,16+/m0/s1

2.1.3 InChI Key

SRPXSILJHWNFMK-MEDUHNTESA-N

2.1.4 Canonical SMILES

C1CC(C2=CC=CC=C2C1C3=CC(=C(C=C3)Cl)Cl)N

2.1.5 Isomeric SMILES

C1C[C@H](C2=CC=CC=C2[C@@H]1C3=CC(=C(C=C3)Cl)Cl)N

2.2 Other Identifiers

2.2.1 UNII

4D28EY0L5T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine

2.3.2 Depositor-Supplied Synonyms

1. 675126-05-3

2. (1r,4s)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine

3. (1r,4s)-trans-norsertraline

4. Norsertraline, (1r,4s)-trans-

5. Sep-225289

6. 4d28ey0l5t

7. Dasotraline [usan:inn]

8. Unii-4d28ey0l5t

9. Dasotraline [inn]

10. Dasotraline (usan/inn)

11. Dasotraline [usan]

12. Dasotraline [who-dd]

13. Schembl263142

14. Dasotraline(sep-225289)

15. Dasotraline; Sep 225289

16. Gtpl8308

17. Chembl3301595

18. Dtxsid20217855

19. Bcp24754

20. Ex-a2622

21. Zinc2510873

22. Dasotraline(sep-225289) Free Base

23. Db12305

24. Sep-225,289

25. Ac-36184

26. Hy-12850

27. Cs-0012724

28. D10700

29. A857937

30. Q27076989

31. (1r,4s)-4-(3,4-dichloro-phenyl)-1,2,3,4-tetrahydro-naphthalen-1-ylamine

32. 4beta-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalene-1alpha-amine

33. 1-naphthalenamine, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-, (1r,4s)-

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₅Cl₂N
Molecular Weight	292.2 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	1
Exact Mass	291.0581549 g/mol
Monoisotopic Mass	291.0581549 g/mol
Topological Polar Surface Area	26 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	309
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Mechanism of Action

Dasotraline has been shown in preclinical studies to be a potent and balanced reuptake inhibitor of serotonin, norepinephrine and dopamine (SNDRI). Serotonin, norepinephrine and dopamine are neurotransmitters associated with depression. There are currently no marketed treatments for depression that inhibit reuptake of all three neurotransmitters.

Drugs in Development