Dasotraline

Dasotraline

Systematic (IUPAC) name
(1R,4S)-4-(3,4-Dichlorophenyl)-1,2,3,4-tetrahydro-1-naphthalenamine
Identifiers
CAS Number	675126-05-3 Y
PubChem	CID: 9947999
ChemSpider	8123611 N
UNII	4D28EY0L5T Y
ChEMBL	CHEMBL3301595
Chemical data
Formula	C16H15Cl2N
Molecular mass	292.20 g·mol−1
SMILES C1C[C@H](C2=CC=CC=C2[C@@H]1C3=CC(=C(C=C3)Cl)Cl)N
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 Key:SRPXSILJHWNFMK-MEDUHNTESA-N
NY (what is this?)  (verify)

Dasotraline (INN) (former developmental code name SEP-225,289) is a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI) that is under development by Sunovion for clinical use. The drug is no longer being developed for major depressive disorder (MDD), but is still under investigation for the treatment of attention-deficit hyperactivity disorder (ADHD) and eating disorders. Structurally, dasotraline is a stereoisomer of desmethylsertraline, which is an active metabolite of the marketed selective serotonin reuptake inhibitor (SSRI) antidepressant sertraline (Zoloft) and an SNDRI similarly.

Side Effects

In phase I trials for ADHD, test subjects reported the following side effects:

• Loss of appetite
• Dehydration
• Cottonmouth
• Nausea
• Insomnia
• Anxiety
• Panic attacks
• Headaches

See also

• Centanafadine
• Indatraline
• Lometraline
• Tametraline

Further reading

Liming Shao Patent

• US application 2007203111, Shao L, Wang F, Malcolm SC, Hewitt MC, Bush LR, Ma J, Varney MA, Campbell U, Engel SR, Hardy LW, Koch P, Campbell JE, "Cycloalkylamines as monoamine reuptake inhibitors", published 2007-08-30, assigned to Sepracor Inc. 

Asymmetry Patent

• US patent 7129378, Han X, Krishnamurthy D, Senanayake CH, Lu Z-H, "Method of preparing amine stereoisomers", published 2005-07-28, assigned to Apsinterm LLC