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F133

Sigma-Aldrich

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:
57226-68-3
Molecular Weight:
331.76
MDL number:
MFCD01321043
UNSPSC Code:
12352200
PubChem Substance ID:
24894760
NACRES:
NA.77

Quality Level

100

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. 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

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.

Caution

Hygroscopic, photosensitive

Legal Information

Sold under license from Eli Lilly and Company.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Antônio Felipe Felicioni Oliveira et al.
Journal of pharmaceutical and biomedical analysis, 73, 53-58 (2012-05-05)
A two-phase liquid phase microextraction using a hollow fiber combined with injection port derivatization and gas chromatographic analysis was developed for extracting and detecting fluoxetine (FLU) and norfluoxetine (NOR) in human plasma. Simultaneous extraction in a multiple tube shaker was
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
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
Lushan Yu et al.
Journal of chromatography. A, 1236, 97-104 (2012-03-23)
In this study, we developed an LC-MS/MS method based on an isotope discrimination mass spectroscopy solution (IDMSS) technology to simultaneously quantify enantiomers of fluoxetine (FLX) and norfluoxetine (NFLX) in a CYP2C9 incubation mixture. S-FLX and S-NFLX were labeled to form
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