Desmethylsertraline

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Desmethylsertraline
Skeletal formula of desmethylsertraline
Ball-and-stick model of the desmethylsertraline molecule
Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Pharmacokinetic data
Elimination half-life66 hours
Excretionurine
Identifiers
  • (1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H15Cl2N
Molar mass292.20 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1Cl)[C@H]3c2c(cccc2)[C@@H](N)CC3

Desmethylsertraline (DMS), also known as norsertraline, is an active metabolite of the antidepressant drug sertraline. Like sertraline, desmethylsertraline acts as a monoamine reuptake inhibitor, and may be responsible for some of its parent's therapeutic benefits. However, DMS is significantly less potent relative to sertraline as a serotonin reuptake inhibitor (Ki = 76 nM vs. 3 nM, respectively), but conversely, is more balanced as a monoamine reuptake inhibitor (5-HT (Ki) = 76 nM; NE (Ki) = 420 nM; DA (Ki) = 440 nM), which has the effective result of DMS contrarily behaving as a serotonin-norepinephrine-dopamine reuptake inhibitor (SNDRI), with about 5.5-fold preference for inhibiting serotonin reuptake relative to catecholamine reuptake.[1]

Dasotraline, a stereoisomer of DMS, is also an SNDRI, and has been investigated for the potential clinical treatment of major depressive disorder, attention-deficit disorder, and eating disorders, but has not been approved or marketed for any indication.

See also[]

References[]

  1. ^ Wong DT, Bymaster FP, Engleman EA (1995). "Prozac (fluoxetine, Lilly 110140), the first selective serotonin uptake inhibitor and an antidepressant drug: twenty years since its first publication". Life Sci. 57 (5): 411–41. doi:10.1016/0024-3205(95)00209-o. PMID 7623609.
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