Synonym
Albalon Liquifilm; Nafazair; Naphazoline HCl; Rhinantin; Vasocon
IUPAC/Chemical Name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole hydrochloride
InChi Key
DJDFFEBSKJCGHC-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H14N2.ClH/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;/h1-7H,8-10H2,(H,15,16);1H
SMILES Code
[H]Cl.C1(CC2=C3C=CC=CC3=CC=C2)=NCCN1
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
>2 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
2934.99.9001
Biological target:
Naphazoline (Naphthazoline) hydrochloride is a potent α-adrenergic receptor agonist.
In vitro activity:
This study discovered that the α1-adrenergic agonists naphazoline, oxymetazoline and also the α1-adrenergic antagonist benoxathian are able to raise the intracellular Ca2+-content in K562 cells. Furthermore, this study demonstrates that naphazoline treatment induces ROS-formation as well as an increase in Δψm in K562 cells.
Reference: Exp Cell Res. 2011 Dec 10;317(20):2969-80. https://pubmed.ncbi.nlm.nih.gov/21851819/
In vivo activity:
An allergic conjunctivitis mouse model was established using histamine or an antigen (ovalbumin), following which mice were treated with 1% olopatadine solution and/or 0.2 mg/ml of naphazoline hydrochloride. The results indicated that olopatadine and naphazoline hydrochloride significantly suppressed conjunctival dye leakage in mice with histamine or antigen‑induced conjunctival vascular hyperpermeability. In addition, treatment with olopatadine and naphazoline hydrochloride was able to reduce the levels of inflammatory factors (TNF‑α, IL‑1β and IL‑6), cytokines (IFN‑γ and IL‑4), IgE, GMCSF, and NGF in antigen‑induced conjunctival vascular hyperpermeability mice.
Reference: Mol Med Rep. 2016 Apr;13(4):3319-25. https://pubmed.ncbi.nlm.nih.gov/26936233/
|
Solvent |
mg/mL |
mM |
| Solubility |
| Water |
49.5 |
200.62 |
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
246.74
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. Fuchs R, Schraml E, Leitinger G, Letofsky-Papst I, Stelzer I, Haas HS, Schauenstein K, Sadjak A. α1-adrenergic drugs exhibit affinity to a thapsigargin-sensitive binding site and interfere with the intracellular Ca2+ homeostasis in human erythroleukemia cells. Exp Cell Res. 2011 Dec 10;317(20):2969-80. doi: 10.1016/j.yexcr.2011.08.003. Epub 2011 Aug 9. PMID: 21851819.
2. Quan L, He H. Treatment with olopatadine and naphazoline hydrochloride reduces allergic conjunctivitis in mice through alterations in inflammation, NGF and VEGF. Mol Med Rep. 2016 Apr;13(4):3319-25. doi: 10.3892/mmr.2016.4937. Epub 2016 Feb 23. PMID: 26936233.
3. Tanaka Y, Mizutani N, Fujii M, Nabe T, Kohno S. Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):144-54. doi: 10.1016/j.prostaglandins.2006.06.003. Epub 2006 Jul 25. PMID: 16939879.
In vitro protocol:
1. Fuchs R, Schraml E, Leitinger G, Letofsky-Papst I, Stelzer I, Haas HS, Schauenstein K, Sadjak A. α1-adrenergic drugs exhibit affinity to a thapsigargin-sensitive binding site and interfere with the intracellular Ca2+ homeostasis in human erythroleukemia cells. Exp Cell Res. 2011 Dec 10;317(20):2969-80. doi: 10.1016/j.yexcr.2011.08.003. Epub 2011 Aug 9. PMID: 21851819.
In vivo protocol:
1. Quan L, He H. Treatment with olopatadine and naphazoline hydrochloride reduces allergic conjunctivitis in mice through alterations in inflammation, NGF and VEGF. Mol Med Rep. 2016 Apr;13(4):3319-25. doi: 10.3892/mmr.2016.4937. Epub 2016 Feb 23. PMID: 26936233.
2. Tanaka Y, Mizutani N, Fujii M, Nabe T, Kohno S. Different mechanisms between thromboxane A2- and leukotriene D4-induced nasal blockage in guinea pigs. Prostaglandins Other Lipid Mediat. 2006 Sep;80(3-4):144-54. doi: 10.1016/j.prostaglandins.2006.06.003. Epub 2006 Jul 25. PMID: 16939879.
1: van Montfrans GA, van Steenwijk RP, Vyth A, Borst C. Intravenous naphazoline intoxication. Acta Med Scand. 1981;209(5):429-30. PubMed PMID: 7246278.
2: Uncini A, De Nicola G, Di Muzio A, Rancitelli G, Colangelo L, Gambi D, Gallenga PE. Topical naphazoline in treatment of myopathic ptosis. Acta Neurol Scand. 1993 Apr;87(4):322-4. PubMed PMID: 8503264.
3: Dockhorn RJ, Duckett TG. Comparison of Naphcon-A and its components (naphazoline and pheniramine) in a provocative model of allergic conjunctivitis. Curr Eye Res. 1994 May;13(5):319-24. PubMed PMID: 8055694.
4: van de Donk HJ, Zuidema J, Merkus FW. Correlation between the sensitivity of the ciliary beat frequency of human adenoid tissue and chicken embryo tracheas for some drugs. Rhinology. 1982 Jun;20(2):81-7. PubMed PMID: 6180466.
5: Le Pelley E, Klossek JM, Bouquet S, Ferrier B, Fusciardi J. [Cocaine contact anesthesia for endonasal surgery. Kinetics and clinical tolerance of a concentrated solution]. Ann Fr Anesth Reanim. 1995;14(6):472-7. French. PubMed PMID: 8745970.
6: Hiramoto T, Kushida H, Endoh M. Further characterization of the myocardial alpha-adrenoceptors mediating positive inotropic effects in the rabbit myocardium. Eur J Pharmacol. 1988 Aug 2;152(3):301-10. PubMed PMID: 2906004.
