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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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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E K Sawyer et al.
Pharmacology, 88(1-2), 44-49 (2011-07-16)
Fluoxetine (Prozac) is a selective serotonin reuptake inhibitor currently used to treat depression and mood disorders. It has been widely studied clinically and preclinically, yet there is limited knowledge of its pharmacokinetics in nonhuman primates. The present study characterized the
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
Dorothy Sit et al.
Journal of clinical psychopharmacology, 30(4), 381-386 (2010-07-16)
To add to the limited data on the clinical pharmacology of antidepressants during pregnancy, we examined the dose-corrected chiral and racemic levels (level/dose) of fluoxetine (FLX) and norfluoxetine (NorFLX) during pregnancy and early postpartum. The authors evaluated 17 pregnant women
W Abdel-Razaq et al.
Neurochemical research, 36(2), 327-338 (2010-12-02)
The in vitro effects of antidepressant drugs on mitochondrial function were investigated in a CHOβ(2)SPAP cell line used previously to determine the effects of antidepressants on gene transcription (Abdel-Razaq et al., Biochem Pharmacol 73:1995-2003, 2007) and in rat heart isolated
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