F133
Norfluoxetine hydrochloride
≥97%, solid
Synonym(s):
(±)-γ-(4-Trifluoromethylphenoxy)benzenepropanamine hydrochloride
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About This Item
Empirical Formula (Hill Notation):
C16H16F3NO · HCl
CAS Number:
Molecular Weight:
331.76
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
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Quality Level
assay
≥97%
form
solid
color
yellow
solubility
H2O: >4 mg/mL
DMSO: >5 mg/mL
SMILES string
Cl[H].NCCC(Oc1ccc(cc1)C(F)(F)F)c2ccccc2
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
InChI key
GMTWWEPBGGXBTO-UHFFFAOYSA-N
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Application
Norfluoxetine hydrochloride has been used to examine if psychoactive pharmaceuticals in drinking water at environmental concentrations could induce neuronal gene expression.[1] 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.[2]
Biochem/physiol Actions
Fluoxetine metabolite; more potent inhibitor of serotonin uptake than fluoxetine with a half-life in vivo of 5-7 days.
Norfluoxetine is an active metabolite of fluoxetine. It disturbs the production of estrogen in a co-culture model of the feto-placental unit.[3]
Caution
Hygroscopic, photosensitive
Legal Information
Sold under license from Eli Lilly and Company.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Jun Zuo et al.
Antimicrobial agents and chemotherapy, 56(9), 4838-4844 (2012-07-04)
No antiviral drugs currently exist for the treatment of enterovirus infections, which are often severe and potentially life threatening. Molecular screening of small molecule libraries identified fluoxetine, a selective serotonin reuptake inhibitor, as a potent inhibitor of coxsackievirus replication. Fluoxetine
Victoria K H Barclay et al.
Journal of chromatography. A, 1227, 105-114 (2012-01-24)
The isotope-labeled compounds fluoxetine-d₅ and norfluoxetine-d₅ were used to study matrix effects caused by co-eluting compounds originating from raw and treated wastewater samples, collected in Uppsala, Sweden. The matrix effects were investigated by the determination of matrix factors (MF) and
D T Wong et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 8(4), 337-344 (1993-06-01)
Like fluoxetine, the N-demethylated metabolite norfluoxetine exists in R- and S-enantiomeric forms. S-Norfluoxetine inhibited serotonin (5-HT) uptake and [3H]paroxetine binding to 5-HT uptake sites with a pKi of 7.86 and 8.88 or 14 and 1.3 nM, respectively, whereas R-norfluoxetine was
Robert K McNamara et al.
Progress in neuro-psychopharmacology & biological psychiatry, 34(7), 1317-1321 (2010-07-27)
Omega-3 (n-3) polyunsaturated fatty acids (PUFA) and fluoxetine (FLX) have additive effects in the treatment of major depressive disorder, and FLX up-regulates genes that regulate fatty acid biosynthesis in vitro. Although these data suggest that FLX may augment n-3 fatty
M Koelch et al.
Pharmacopsychiatry, 45(2), 72-76 (2011-11-17)
Information about therapeutic serum levels of fluoxetine (FLX) and its major metabolite norfluoxetine (NORFLX) in children and adolescents is scarce. Therapeutic drug monitoring (TDM) of FLX was routinely performed in 71 subjects treated for a major depressive disorder (MDD) (10-60
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