Basic information
- CAS
10061-11-7- Standard SMILES
c1ccc2c(CC3=NCCN3)cccc2c1- InChIKey
CNIIGCLFLJGOGP-UHFFFAOYSA-N- Molecular formula
- C14H14N2
- Average molar mass
- 210.27 g/mol
- Monoisotopic mass
- 210.11569846
Overview
2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole is a member of naphthalenes.
Names & identifiers
- Preferred name
- Naphazoline
- IUPAC
- 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole
- English name
- Naphazoline
- Molecular formula
- C14H14N2
- Molecular weight
- 210.27
Names & synonyms
naphazoline835-31-42-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazoleNafazolinaClearineNafazolinNaphazolinum2-(1-Naphthylmethyl)-2-imidazolineCiba 2020/Ralpha-Naphthylmethyl imidazoline1H-Imidazole, 4,5-dihydro-2-(1-naphthalenylmethyl)-DTXSID3048449
Show more names
NAPHAZOLINE HCLNAFAZOLINENaphazoline-d42-(1-NAPHTHYLMETHYL)-2-IMIDAZOLINE HYDROCHLORIDEAntanImidinPrivineSanorinRhinazineciba2020/r
H231GF11BVDTXCID90198485Tele StullnAK ConVasoconstrictor PensaPensa, VasoconstrictorRefChem:56335naphthizinum (for the nitrate)
Database identifiers
- CAS
10061-11-7、835-31-4- PubChem CID
- 4436
- DTXSID
DTXSID3048449
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 24.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 272
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Physical DescriptionSolid
Collision Cross Section
149.6 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
147.59 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 254 °C · 254 °C
- Boiling point
- 339.81 °C · 339.81°C (rough estimate)
- Density
- 1.1063 · 1.1063 (rough estimate)
- refractive index
- 1.618 · 1.6180 (estimate)
- storage temp.
- 2 · 2-8°C
- pka
- 10.35 · pKa 10.35 ± 0.02(H2O,t =25,Iundefined) (Uncertain)
- form
- Solid
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationREACH registered substance: Naphazoline (EC: 212-641-5)
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- rtecs
- NJ4375000
- ridadr
- UN 2811 6.1/PG 2
- risk_code
- 25
- hazard_code
- T
- safety_code
- 45
- REACH Registrations
- Inactive
Chemistry & industry
Pharmacology
ATC Code
R01AA08
S - Sensory organs
R - Respiratory system
R - Respiratory system
QR - Respiratory system
QR - Respiratory system
Protein BindingProtein binding data for naphazoline is unavailable.
PharmacodynamicsNaphazoline is a sympathomimetic alpha adrenergic agonist that acts to vasoconstrict nasal or ocular arterioles, resulting in reduced congestion at the site of administration.
Mechanism of Action
Naphazoline is a vasoconstrictor that functions by stimulating alpha adrenergic receptors in arterioles leading to decreased congestion at the site of administration. Naphazoline causes the release of norepinephrine in sympathetic nerves. Norepinephrine binds to alpha adrenergic receptors and causes vasoconstriction. Naphazoline is also a mild beta adrenergic receptor agonist, which can cause rebound vasodilation after the alpha adrenergic stimulation has ended. Naphazoline's release of norepinephrine also triggers a negative feedback loop which decreases production of norepinephrine, which can lead to rhinitis medicamentosa after long term use when naphazoline is stopped.
Biological Half-LifeHalf life has not been determined but effects last for 4 to 8 hours. Other imidazoline compounds have half lives varying from 2 to 12 hours.
Metabolism/MetabolitesMetabolism data for naphazoline are scarce. Imidazoline compounds undergo some hepatic metabolism but a large fraction of the dose may be excreted unchanged in the urine.
MeSH Pharmacological Classification
Drugs that selectively bind to and activate alpha adrenergic receptors.
Drugs designed to treat inflammation of the nasal passages, generally the result of an infection (more often than not the common cold) or an allergy related condition, e.g., hay fever. The inflammation involves swelling of the mucous membrane that lines the nasal passages and results in inordinate mucus production. The primary class of nasal decongestants are vasoconstrictor agents. (From PharmAssist, The Family Guide to Health and Medicine, 1993)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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