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Naphazoline

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Naphazoline
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Systematic (IUPAC) name
2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
Clinical data
Trade names Naphcon-a
AHFS/Drugs.com monograph
Topical
Identifiers
835-31-4 7pxN
R01AA08 S01GA01
PubChem CID 4436
DrugBank DB06711 7pxY
ChemSpider 4283 7pxY
UNII H231GF11BV 7pxY
KEGG D08253 7pxY
ChEMBL CHEMBL761 7pxY
Chemical data
Formula C14H14N2
210.274
 14pxN (what is this?)  (verify)

Naphazoline (in the hydrochloride form) is the common name for 2-(1-naphthylmethyl)-2-imidazoline hydrochloride. It is a sympathomimetic agent with marked alpha adrenergic activity. It is a vasoconstrictor with a rapid action in reducing swelling when applied to mucous membrane. It acts on alpha-receptors in the arterioles of the conjunctiva to produce constriction, resulting in decreased congestion. It is an active ingredient in several over-the-counter formulations including Clear Eyes and Naphcon eye drops.[1]

It has the molecular formula C14H14N2.HCl and a molecular weight of 246.73 g/mol.

Warnings and contraindications

A few warnings and contraindications that apply to all naphazoline-containing substances intended for medicinal use are:

A possible association with stroke has been suggested.[2]

Chemistry

Naphazoline can be synthesized from (1-naphthyl)acetonitrile, which upon reaction with ethanol transforms into iminoester, and undergoes further heterocyclization into the desired imidazoline derivative upon reaction with ethylene diamine.[3]

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References

  1. ^ Green, S. M. (2008). "Ophthalmology: Naphazoline". Tarascon Pocket Pharmacopoeia 2009. Jones and Bartlett. ISBN 0-7637-6572-4. 
  2. ^ Zavala, J. A.; Pereira, E. R.; Zétola, V. H.; Teive, H. A.; Nóvak, E. M.; Werneck, L. C. (2004). "Hemorrhagic stroke after naphazoline exposition: case report". Arquivos de Neuro-Psiquiatrica 62 (3B): 889–891. PMID 15476091. doi:10.1590/S0004-282X2004000500030. 
  3. ^ A. Sonn, U.S. Patent 2,161,938 (1939)