Naphazoline

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

MedKoo CAT#: 318305

CAS#: 835-31-4

Description: 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.


Price and Availability

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Naphazoline is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318305
Name: Naphazoline
CAS#: 835-31-4
Chemical Formula: C14H14N2
Exact Mass: 210.1157
Molecular Weight: 210.2744
Elemental Analysis: C, 79.97; H, 6.71; N, 13.32


Synonym: Naphazoline, Naphcon-a, AK-Con, All Clear, Clear Eyes

IUPAC/Chemical Name: 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole

InChi Key: CNIIGCLFLJGOGP-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H14N2/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)

SMILES Code: C1(CC2=C3C=CC=CC3=CC=C2)=NCCN1


Technical Data

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, not in water

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).

Harmonized System Code:
293490


References

1: Oliveira Tda C, Freitas JM, Abarza Munoz RA, Richter EM. A batch injection analysis system with square-wave voltammetric detection for fast and simultaneous determination of naphazoline and zinc. Talanta. 2016 May 15;152:308-13. doi: 10.1016/j.talanta.2016.02.031. Epub 2016 Feb 15. PubMed PMID: 26992525.

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. PubMed PMID: 26936233.

3: Liguori C, Garaci F, Romigi A, Mercuri NB, Marciani MG, Placidi F. Bilateral thalamic stroke due to nasal ephedrine and naphazoline use. Neurol Sci. 2015 Jul;36(7):1285-6. doi: 10.1007/s10072-014-2030-z. Epub 2014 Dec 20. PubMed PMID: 25527367.

4: Hoang VD, Hue NT, Tho NH, Nguyen HM. Simultaneous determination of chloramphenicol, dexamethasone and naphazoline in ternary and quaternary mixtures by RP-HPLC, derivative and wavelet transforms of UV ratio spectra. Spectrochim Acta A Mol Biomol Spectrosc. 2015 Mar 15;139:20-7. doi: 10.1016/j.saa.2014.11.101. Epub 2014 Dec 12. PubMed PMID: 25546493.

5: Pemberton JD, MacIntosh PW, Zeglam A, Fay A. Naphazoline as a confounder in the diagnosis of carotid artery dissection. Ophthal Plast Reconstr Surg. 2015 Mar-Apr;31(2):e33-5. doi: 10.1097/IOP.0000000000000059. PubMed PMID: 24807801.

6: Imani-Nabiyyi A, Sorouraddin MH. Determination of naphazoline hydrochloride in biological and pharmaceutical samples by a quantum dot-assisted chemiluminescence system using response-surface methodology. Luminescence. 2014 Dec;29(8):994-1002. doi: 10.1002/bio.2649. Epub 2014 Apr 14. PubMed PMID: 24733642.

7: Huang T, Chen N, Wang D, Lai Y, Cao Z. A validated stability-indicating HPLC method for the simultaneous determination of pheniramine maleate and naphazoline hydrochloride in pharmaceutical formulations. Chem Cent J. 2014 Feb 1;8(1):7. doi: 10.1186/1752-153X-8-7. PubMed PMID: 24485011; PubMed Central PMCID: PMC3931327.

8: Iranifam M, Sorouraddin MH. Flow injection chemiluminescence determination of naphazoline hydrochloride in pharmaceuticals. Luminescence. 2014 Feb;29(1):48-51. doi: 10.1002/bio.2500. Epub 2013 Mar 6. PubMed PMID: 23463582.

9: Marszałł MP, Sroka WD, Balinowska A, Mieszkowski D, Koba M, Kaliszan R. Ionic liquids as mobile phase additives for feasible assay of naphazoline in pharmaceutical formulation by HPTLC-UV-densitometric method. J Chromatogr Sci. 2013 Jul;51(6):560-5. doi: 10.1093/chromsci/bms168. Epub 2012 Oct 16. PubMed PMID: 23076785.

10: Ali NW, Hegazy MA, Abdelkawy M, Abdelfatah RM. Report: Simultaneous determination of naphazoline hydrochloride, chlorpheniramine maleate and methylene blue in their ternary mixture. Pak J Pharm Sci. 2013 May;26(3):641-8. PubMed PMID: 23625443.

11: Di Lorenzo C, Coppola G, La Salvia V, Pierelli F. Nasal decongestant and chronic headache: a case of naphazoline overuse headache? F1000Res. 2013 Nov 11;2:237. doi: 10.12688/f1000research.2-237.v1. eCollection 2013. PubMed PMID: 25110575; PubMed Central PMCID: PMC4111119.

12: Zhu S, Liu Y. Spectroscopic analyses on interaction of Naphazoline hydrochloride with bovine serum albumin. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Dec;98:142-7. doi: 10.1016/j.saa.2012.08.040. Epub 2012 Aug 23. PubMed PMID: 22995546.

13: Peralta CM, Silva RA, Fernández LP, Masi AN. Online naphazoline quality control by micellar-enhanced spectrofluorimetry. Luminescence. 2011 Nov-Dec;26(6):689-95. doi: 10.1002/bio.1297. Epub 2011 May 2. PubMed PMID: 21538792.

14: Nagane Y, Utsugisawa K, Suzuki S, Masuda M, Shimizu Y, Utsumi H, Uchiyama S, Suzuki N. Topical naphazoline in the treatment of myasthenic blepharoptosis. Muscle Nerve. 2011 Jul;44(1):41-4. doi: 10.1002/mus.22002. Epub 2011 Apr 12. PubMed PMID: 21491460.

15: Frag EY, Mohamed GG, El-Dien FA, Mohamed ME. Construction and performance characterization of screen printed and carbon paste ion selective electrodes for potentiometric determination of naphazoline hydrochloride in pharmaceutical preparations. Analyst. 2011 Jan 21;136(2):332-9. doi: 10.1039/c0an00343c. Epub 2010 Oct 20. PubMed PMID: 20959926.

16: Asadpour-Zeynali K, Ghavami R, Esfandiari R, Soheili-Azad P. Simultaneous determination of antazoline and naphazoline by the net analyte signal standard addition method and spectrophotometric technique. J AOAC Int. 2010 Nov-Dec;93(6):1995-2001. PubMed PMID: 21313830.

17: Klein KU, Wisser G, Engelhard K, Werner C. Pulmonary edema and prolonged awakening after nasal naphazoline application in a transspenoidal hypophysectomy patient. J Neurosurg Anesthesiol. 2010 Jul;22(3):269. doi: 10.1097/ANA.0b013e3181dcb5b8. PubMed PMID: 20548172.

18: Criado S, García NA. A comparative kinetic and mechanistic study between tetrahydrozoline and naphazoline toward photogenerated reactive oxygen species. Photochem Photobiol. 2010 Jan-Feb;86(1):23-30. doi: 10.1111/j.1751-1097.2009.00616.x. Epub 2009 Aug 26. PubMed PMID: 19709378.

19: Yamadori Y, Oiso N, Hirao A, Kawara S, Kawada A. Allergic contact dermatitis from dibucaine hydrochloride, chlorpheniramine maleate, and naphazoline hydrochloride in an over-the-counter topical antiseptic. Contact Dermatitis. 2009 Jul;61(1):52-3. doi: 10.1111/j.1600-0536.2009.01556.x. PubMed PMID: 19659969.

20: Wang NN, Shao YQ, Tang YH, Yin HP, Wu XZ. Flow-injection chemiluminescence method for the determination of naphazoline hydrochloride and oxymetazoline hydrochloride. Luminescence. 2009 May-Jun;24(3):178-82. doi: 10.1002/bio.1092. PubMed PMID: 19253271.