Desmethylsertraline

Desmethylsertraline

Systematic (IUPAC) name
(1S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-amine
Legal status
Legal status	uncontrolled
Pharmacokinetic data
Biological half-life	66 hours
Excretion	urine
Identifiers
CAS Number	87857-41-8
ATC code	none
PubChem	CID 114743
ChemSpider	102729
Chemical data
Formula	C16H15Cl2N
Molar mass	292.20 g/mol
SMILES 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 (K_i = 76 nM vs. 3 nM, respectively), but conversely, is more balanced as a monoamine reuptake inhibitor (5-HT (K_i) = 76 nM; NE (K_i) = 420 nM; DA (K_i) = 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

• Desmethylcitalopram
• Desmethylvenlafaxine
• Didesmethylcitalopram
• Indatraline
• Lometraline
• Norfluoxetine
• Tametraline

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.