Naphazoline HCl | CAS#550-99-2 | α1-Adrenergic receptor agonist

Naphazoline HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540308

CAS#: 550-99-2

Description: Naphazoline HCl is an α1-Adrenergic receptor agonist used to treat congestion and ocular pathologies. It also induces autophagy and necrotic cell death in erythroleukemia cells and inhibits erythroid differentiation.

Chemical Structure

Naphazoline HCl

CAS# 550-99-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 540308
Name: Naphazoline HCl
CAS#: 550-99-2
Chemical Formula: C14H15ClN2
Exact Mass: 246.09
Molecular Weight: 246.738
Elemental Analysis: C, 68.15; H, 6.13; Cl, 14.37; N, 11.35

Price and Availability

Size	Price	Availability	Quantity
10g	USD 200
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Appearance: Solid powder

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

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Product Data:

Product Data

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	Water	49.5	200.62

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.

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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.

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