Synonym
Norfluoxetine hydrochloride; Norfluoxetine HCl
IUPAC/Chemical Name
3-Phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-amine hydrochloride
InChi Key
GMTWWEPBGGXBTO-UHFFFAOYSA-N
InChi Code
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
SMILES Code
NCCC(C1=CC=CC=C1)OC2=CC=C(C(F)(F)F)C=C2.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Norfluoxetine hydrochloride inhibits 5-HT uptake and inhibits CaV3.3 T current (IC50 = 5 μM).
In vitro activity:
The effects of fluoxetine and its major metabolite, norfluoxetine, were studied using the patch-clamp technique on the cloned neuronal rat K(+) channel Kv3.1, expressed in Chinese hamster ovary cells. Norfluoxetine produced use-dependent inhibition of Kv3.1 at a frequency of 1 Hz and slowed the recovery from inactivation. It is concluded that at clinically relevant concentrations, both fluoxetine and its major metabolite norfluoxetine inhibit Kv3.1, and that norfluoxetine directly inhibits Kv3.1 as an open channel blocker.
Reference: Neuropharmacology. 2001 Sep;41(4):443-53. https://pubmed.ncbi.nlm.nih.gov/11543764/
In vivo activity:
Analysis by tyrosine hydroxylase (TH) immunohistochemistry demonstrated that norfluoxetine prevents degeneration of nigrostriatal dopamine neurons in vivo in MPTP-lesioned mice compared to vehicle-treated MPTP-lesioned control mice. MAC-1 immunostaining and hydroethidine histochemical staining showed that norfluoxetine neuroprotection is accompanied by inhibiting MPTP-induced microglial activation and activated microglia-derived reactive oxygen species production in vivo, respectively.
Reference: Mediators Inflamm. 2018 Dec 30;2018:4591289. https://pubmed.ncbi.nlm.nih.gov/30692871/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
90.43 |
| DMSO |
30.0 |
90.43 |
| Ethanol |
30.0 |
90.43 |
| PBS (pH 7.2) |
2.0 |
6.03 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
331.76
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Choi BH, Choi JS, Yoon SH, Rhie DJ, Min DS, Jo YH, Kim MS, Hahn SJ. Effects of norfluoxetine, the major metabolite of fluoxetine, on the cloned neuronal potassium channel Kv3.1. Neuropharmacology. 2001 Sep;41(4):443-53. doi: 10.1016/s0028-3908(01)00088-0. PMID: 11543764.
2. Kim KI, Chung YC, Jin BK. Norfluoxetine Prevents Degeneration of Dopamine Neurons by Inhibiting Microglia-Derived Oxidative Stress in an MPTP Mouse Model of Parkinson's Disease. Mediators Inflamm. 2018 Dec 30;2018:4591289. doi: 10.1155/2018/4591289. PMID: 30692871; PMCID: PMC6332876.
3. Fuller RW, Snoddy HD. Role of norfluoxetine in the inhibition of desipramine metabolism and in the inhibition of serotonin uptake after fluoxetine administration to rats. Res Commun Chem Pathol Pharmacol. 1991 Jul;73(1):31-40. PMID: 1715593.
In vitro protocol:
1. Choi BH, Choi JS, Yoon SH, Rhie DJ, Min DS, Jo YH, Kim MS, Hahn SJ. Effects of norfluoxetine, the major metabolite of fluoxetine, on the cloned neuronal potassium channel Kv3.1. Neuropharmacology. 2001 Sep;41(4):443-53. doi: 10.1016/s0028-3908(01)00088-0. PMID: 11543764.
In vivo protocol:
1. Kim KI, Chung YC, Jin BK. Norfluoxetine Prevents Degeneration of Dopamine Neurons by Inhibiting Microglia-Derived Oxidative Stress in an MPTP Mouse Model of Parkinson's Disease. Mediators Inflamm. 2018 Dec 30;2018:4591289. doi: 10.1155/2018/4591289. PMID: 30692871; PMCID: PMC6332876.
2. Fuller RW, Snoddy HD. Role of norfluoxetine in the inhibition of desipramine metabolism and in the inhibition of serotonin uptake after fluoxetine administration to rats. Res Commun Chem Pathol Pharmacol. 1991 Jul;73(1):31-40. PMID: 1715593.
1: Shi S, Liu Y, Wu J, Li Z, Zhao Y, Zhong D, Zeng F. Comparative bioavailability and tolerability of a single 20-mg dose of two fluoxetine hydrochloride dispersible tablet formulations in fasting, healthy Chinese male volunteers: an open-label, randomized-sequence, two-period crossover study. Clin Ther. 2010 Oct;32(11):1977-86. doi: 10.1016/j.clinthera.2010.10.003. PubMed PMID: 21095492.
2: Keller T, Cambon N, Genevray M, Crivelli F, Crivelli M, Dal BL, Mazzucchelli P, Ismaili S, Marzo A. Bioequivalence study of fluoxetine hydrochloride in healthy volunteers. Arzneimittelforschung. 2005;55(9):491-7. PubMed PMID: 16229112.
3: Pohland RC, Bernhard NR. Postmortem serum and tissue redistribution of fluoxetine and norfluoxetine in dogs following oral administration of fluoxetine hydrochloride (Prozac). J Forensic Sci. 1997 Sep;42(5):812-6. PubMed PMID: 9304827.
4: Spencer MJ. Fluoxetine hydrochloride (Prozac) toxicity in a neonate. Pediatrics. 1993 Nov;92(5):721-2. PubMed PMID: 8414864.
5: Lester BM, Cucca J, Andreozzi L, Flanagan P, Oh W. Possible association between fluoxetine hydrochloride and colic in an infant. J Am Acad Child Adolesc Psychiatry. 1993 Nov;32(6):1253-5. PubMed PMID: 8282672.
