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NORFLUOXETINE HYDROCHLORIDE

Product NameNORFLUOXETINE HYDROCHLORIDE
CAS57226-68-3
MFC16H17ClF3NO
MW331.76
EINECS
MOL File57226-68-3.mol

Chemical Properties

storage temp.	-20°C
solubility	H₂O: >4 mg/mL
form	solid
color	yellow
Water Solubility	H2O: >4mg/mL DMSO: >5mg/mL
Stability	Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI	1S/C16H16F3NO.ClH/c17-16(18,19)13-6-8-14(9-7-13)21-15(10-11-20)12-4-2-1-3-5-12;/h1-9,15H,10-11,20H2;1H
InChIKey	GMTWWEPBGGXBTO-UHFFFAOYSA-N
SMILES	Cl[H].NCCC(Oc1ccc(cc1)C(F)(F)F)c2ccccc2

Safety Information

WGK Germany	3
Storage Class	11 - Combustible Solids

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Norfluoxetine is an active metabolite of the antidepressant fluoxetine. It is formed from fluoxetine by the cytochrome P450 (CYP) isoforms CYP2C9, CYP2C19, and CYP3A. Norfluoxetine inhibits serotonin (5-HT) uptake in rat brain synaptosomal membrane preparations (K_i = 44.7 nM) and isolated human platelets (IC₅₀ = ~15 nM). It has been found in the tissues of fish exposed to wastewater effluent.

Chemical Properties

NORFLUOXETINE HYDROCHLORIDE is Light Beige to Light Brown Solid

Uses

Norfluoxetine Hydrochloride is a metabolite of Fluoxetine (F597100), a selective serotonin reuptake inhibitor which is used as an antidepressant.

Uses

Norfluoxetine hydrochloride has been used to examine if psychoactive pharmaceuticals in drinking water at environmental concentrations could induce neuronal gene expression. It has also been used to examine whether at environmental concentrations it can alter in vitro expression of autism spectrum disorders (ASD)-associated synaptic proteins in human neurons.

Biochem/physiol Actions

Norfluoxetine is an active metabolite of fluoxetine. It disturbs the production of estrogen in a co-culture model of the feto-placental unit.

in vivo

Pretreatment with Fluoxetine or Norfluoxetine hydrochloride (20mg/kg s.c.), as well as Phenytoin (30 mg/kg s.c.) and Clonazepam (0.1mg/kg s.c.) significantly increases both the rate and duration of survival, demonstrating a significant protective effect against Pentylenetetrazol-induced epilepsy^[1].

IC 50

5-HT Receptor; Ca_V3.3: 5 μM (IC₅₀)

References

[1] CHRISTIAAN C VEERMAN. Slow delayed rectifier potassium current blockade contributes importantly to drug-induced long QT syndrome.[J]. Circulation. Arrhythmia and electrophysiology, 2013, 6 5: 1002-1009. DOI:10.1161/circep.113.000239
[2] JUSTIN D LUTZ. Stereoselective inhibition of CYP2C19 and CYP3A4 by fluoxetine and its metabolite: implications for risk assessment of multiple time-dependent inhibitor systems.[J]. Drug Metabolism and Disposition, 2013, 41 12: 2056-2065. DOI:10.1124/dmd.113.052639
[3] DAVID T. WONG PH.D. Norfluoxetine Enantiomers as Inhibitors of Serotonin Uptake in Rat Brain[J]. Neuropsychopharmacology, 1993, 8 4: 337-344. DOI:10.1038/npp.1993.33
[4] JUN ZUO. Fluoxetine is a potent inhibitor of coxsackievirus replication.[J]. Antimicrobial Agents and Chemotherapy, 2012, 56 9: 4838-4844. DOI:10.1128/aac.00983-12
[5] CONOR MCCLENAGHAN. Polymodal activation of the TREK-2 K2P channel produces structurally distinct open states.[J]. Journal of General Physiology, 2016, 147 6: 497-505. DOI:10.1085/jgp.201611601

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