2315-02-8

Basic information

• Product Name: Oxymetazoline hydrochloride
• Synonyms: 2-(4-t-butyl-2,6-dimethyl-3-hydroxybenzyl)-2-imidazoliniumchloride;2,6-dimethyl-2-(4-tertiarybutyl-3-hydroxyphenyl)methylimidazolinehydrochlori;6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethyl-phenohydrochloride;6-t-butyl-3-(2-imidazolin-2-ylmethyl)-2,4-dimethylphenolhydrochloride;afrazine;afrinhydrochloride;duration;iliadinhydrochloride
• CAS NO: 2315-02-8
• Molecular Formula: C₁₆H₂₄N₂O*ClH
• Molecular Weight: 296.84
• EINECS: 219-015-0
• Product Categories: Adrenoceptor;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;API;PAVABID
• Mol File: 2315-02-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: approximate 300℃ (dec.)
• Boiling Point: 431.9°Cat760mmHg
• Flash Point: 215°C
• Appearance: white/solid
• Density: 1.08g/cm³
• Vapor Pressure: 4.59E-08mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: H2O: soluble
• CAS DataBase Reference: Oxymetazoline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Oxymetazoline hydrochloride(2315-02-8)
• EPA Substance Registry System: Oxymetazoline hydrochloride(2315-02-8)

Safety Data

• Hazard Codes: T+
• Statements: 28
• Safety Statements: 22-28-36/37/39-45
• RIDADR: UN 2811 6.1/PG 1
• WGK Germany: 3
• RTECS: SK1225000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 2315-02-8(Hazardous Substances Data)

Usage

Description

Oxymetazoline hydrochloride is a hydrochloride salt resulting from the reaction of equimolar quantities of oxymetazoline and hydrogen chloride. It is a direct-acting sympathomimetic with marked alpha-adrenergic activity, characterized as a vasoconstrictor used to relieve nasal congestion. Oxymetazoline hydrochloride is an off-white solid and functions as an α1-AR and α2-AR adrenergic receptor agonist.

Uses

Used in Pharmaceutical Industry:
Oxymetazoline hydrochloride is used as a muscle relaxant (smooth) for its ability to induce relaxation in smooth muscles, which can be beneficial in various medical applications.
Used in Cerebral Vasodilation:
Oxymetazoline hydrochloride is used as a cerebral vasodilator to improve blood flow in the brain, which can be helpful in treating certain neurological conditions.
Used in Nasal Decongestant Applications:
Oxymetazoline hydrochloride is used as a vasoconstrictor, specifically as a nasal decongestant, to relieve nasal congestion. It is an ingredient in products like Drixin, which is utilized for this purpose.
Used in Nasal Decongestant Formulations:
As an α1-AR and α2-AR adrenergic receptor agonist, Oxymetazoline hydrochloride is used as a vasoconstrictor in nasal decongestant formulations to provide relief from nasal congestion and improve breathing.

Therapeutic Function

Nasal decongestant

Biological Activity

Partial α 2A adrenoceptor agonist and α 1A agonist. Agonist/antagonist activity at 5-HT receptors.

InChI:InChI=1/C16H24N2O/c1-10-8-13(16(3,4)5)15(19)11(2)12(10)9-14-17-6-7-18-14/h8,19H,6-7,9H2,1-5H3,(H,17,18)/p+1

Synthetic route

Oxymetazoline hydrochloride (2315-02-8) → 6-(tert-butyl)-3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-2,4-dimethylphenyl (R)-5-(1,2-dithiolan-3-yl)pentanoate

Conditions	Yield
Multi-step reaction with 4 steps 1: ammonium hydroxide / 25 - 30 °C 2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 5 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 18 h / 20 - 30 °C / Inert atmosphere 4: hydrogen; palladium 10% on activated carbon / methanol View Scheme

Oxymetazoline hydrochloride (2315-02-8) → C31H42N2O2S2

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide / 25 - 30 °C 2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 5 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 18 h / 20 - 30 °C / Inert atmosphere View Scheme

Oxymetazoline hydrochloride (2315-02-8) → oxymetazoline (1491-59-4)

Conditions	Yield
With ammonium hydroxide at 25 - 30℃;

Oxymetazoline hydrochloride (2315-02-8) → C23H30N2O

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / 25 - 30 °C 2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 5 °C View Scheme

Oxymetazoline hydrochloride (2315-02-8) → C35H52N2O2

Conditions	Yield
Multi-step reaction with 3 steps 1.1: ammonium hydroxide / 25 - 30 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 5 °C 3.1: sodium hydride / tetrahydrofuran / 0 - 5 °C 3.2: 2 h / 0 - 5 °C View Scheme

Oxymetazoline hydrochloride (2315-02-8) → 6-(tert-butyl)-3-((4,5-dihydro-1H-imidazol-2-yl)methyl)-2,4-dimethylphenyl dodecanoate

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ammonium hydroxide / 25 - 30 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 5 °C 3.1: sodium hydride / tetrahydrofuran / 0 - 5 °C 3.2: 2 h / 0 - 5 °C 4.1: hydrogen; palladium 10% on activated carbon / methanol / 12 h / 25 - 30 °C View Scheme

Downstream Products

• 1491-59-4 oxymetazoline 

Relevant articles and documents

Method for the treatment of CNS disorders with substituted 2-imidazoles or imidazole derivatives

The present invention relates a method for treating depression, anxiety disorders, bipolar disorder, attention deficit hyperactivity disorder, stress-related disorders, psychotic disorders such as schizophrenia, neurological diseases such as Parkinson's disease, neurodegenerative disorders such as Alzheimer's disease, epilepsy, migraine, hypertension, substance abuse and metabolic disorders such as eating disorders, diabetes, diabetic complications, obesity, dyslipidemia, disorders of energy consumption and assimilation, disorders and malfunction of body temperature homeostasis, disorders of sleep and circadian rhythm, and cardiovascular disorders which comprises administering to an individual a therapeutically effective amount of a compound of formula I wherein R, R1, R2, A and n are as defined in the specification and to their pharmaceutically active salts. The invention also relates to novel compounds of formula I, pharmaceutical compositions containing them, and methods for their preparation.