57226-68-3 Usage
Description
Norfluoxetine Hydrochloride is an active metabolite of the antidepressant fluoxetine, which is a selective serotonin reuptake inhibitor. 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 and isolated human platelets. It has been found in the tissues of fish exposed to wastewater effluent and is characterized by its light beige to light brown solid appearance.
Uses
Used in Pharmaceutical Industry:
Norfluoxetine Hydrochloride is used as an antidepressant for the treatment of depression and related disorders. It functions by inhibiting the reuptake of serotonin, thereby increasing its availability in the brain and improving mood.
Used in Environmental Research:
Norfluoxetine Hydrochloride is used as a research compound to examine the effects of psychoactive pharmaceuticals in drinking water at environmental concentrations on neuronal gene expression. It is also utilized to study whether, at environmental concentrations, it can alter the in vitro expression of autism spectrum disorders (ASD)-associated synaptic proteins in human neurons.
Used in Toxicology and Ecotoxicology:
Norfluoxetine Hydrochloride is employed in toxicological and ecotoxicological studies to understand the impact of wastewater effluent on aquatic life, particularly in fish, where it has been detected in their tissues. This helps in assessing the potential risks associated with the presence of such metabolites in the environment.
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.
References
1) Veerman?et al.?(2013),?Slow delayed rectifier potassium current blockade contributes importantly to drug-induced long QT syndrome;?Circ. Arrythm. Electrophysiol.?6?1002
2) Lutz?et al.?(2013),?Stereoselective inhibition of CYP2C1 and CYP3A4 by fluoxetine and its metabolite: implications for risk assessment of multiple time-dependent inhibitor systems;?Drug Metab. Dispos.?41?2056
3) Wong?et al.?(1993),?Norfluoxetine enantiomers as inhibitors of serotonin uptake in rat brain;?Neuropsychopharmacology?8?337
4) Zuo?et al.?(2012),?Fluoxetine is a potent inhibitor of coxsackievirus replication.; Antimicrob. Agents Chemother.?56?4838
5) McClenaghan?et al.?(2016),?Polymodal activation of the TREK-2 K2P channel produces structurally distinct open states; J. Gen. Physiol.?147?497
Check Digit Verification of cas no
The CAS Registry Mumber 57226-68-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,2,2 and 6 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 57226-68:
(7*5)+(6*7)+(5*2)+(4*2)+(3*6)+(2*6)+(1*8)=133
133 % 10 = 3
So 57226-68-3 is a valid CAS Registry Number.
InChI:InChI=1/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
57226-68-3Relevant articles and documents
A convenient method for preparing enantiomerically pure norfluoxetine, fluoxetine and tomoxetine
Koenig, Thomas M.,Mitchell, David
, p. 1339 - 1342 (2007/10/02)
A convenient synthesis for enantiomers of norfluoxetine, fluoxetine and tomoxetine is described. All final products were derived from a common intermediate, 3-phenyl-3-hydroxypropylamine.
