2508-72-7

Basic information

• Product Name: Antazoline hydrochloride
• Synonyms: 2-((n-benzylanilino)methyl)-2-imidazolinmonohydrochloride;2-(n-phenyl-n-benzylaminomethyl)imidazolinehydrochloride;2-phenylbenzylaminomethylimidazolinehydrochloride;antistinehydrochloride;fenazolina;histazine;Antazolin Hcl;2-(N-Benzyl-N-phenylaminonomethyl)-2-imidazoline
• CAS NO: 2508-72-7
• Molecular Formula: C₁₇H₁₉N₃*ClH
• Molecular Weight: 301.81
• EINECS: 219-719-8
• Product Categories: Histamine receptor
• Mol File: 2508-72-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 238 °C
• Boiling Point: 475.5 °C at 760 mmHg
• Flash Point: 241.4 °C
• Appearance: White or almost white crystalline powder
• Vapor Pressure: 3.31E-09mmHg at 25°C
• Storage Temp.: Store at RT
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• Merck: 14,680
• CAS DataBase Reference: Antazoline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Antazoline hydrochloride(2508-72-7)
• EPA Substance Registry System: Antazoline hydrochloride(2508-72-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: NJ2150000
• Hazardous Substances Data: 2508-72-7(Hazardous Substances Data)

Usage

Description

Antazoline hydrochloride is a white or almost white crystalline powder that is recognized for its pharmaceutical applications, particularly as an antihistamine and H1 antagonist. It is also known to act as an imidazoline binding site ligand.

Uses

Used in Pharmaceutical Industry:
Antazoline hydrochloride is used as an antihistamine for treating allergic reactions and symptoms such as itching, swelling, and redness. It functions by blocking the action of histamine, a compound released during an allergic response.
Antazoline hydrochloride is used as an H1 antagonist for preventing the effects of histamine on H1 receptors, which are involved in allergic reactions and other conditions like rhinitis and urticaria.
Additionally, Antazoline hydrochloride is used as an imidazoline binding site ligand, which may have potential applications in the treatment of various conditions, although further research is needed to fully understand its implications in this area.

Originator

Antistine HCl,Ciba,US,1948

Manufacturing Process

15.4 parts of 2-chloromethylimidazoline hydrochloride, 45.8 parts of Nbenzylaniline and 150 parts of alcohol are heated in an oil bath at 100° to 110°C. After distilling off the alcohol, the reaction mass is maintained at this temperature for a further 3 hours and then triturated with water and 10 parts of sodium bicarbonate. The unconsumed benzylaniline is extracted with ether and the aqueous solution neutralized with dilute hydrochloric acid. By evaporating this solution and extracting the residue with alcohol there is obtained 2-(N-phenyl-N-benzylaminomethyl)imidazoline hydrochloride in the form of colorless crystals of melting point 227° to 229°C.

Therapeutic Function

Antihistaminic

Biological Activity

Imidazoline binding site ligand; a potent inducer of insulin secretion in rat pancreas. Also an antihistamine.

InChI:InChI=1/C17H19N3/c1-3-7-15(8-4-1)13-20(14-17-18-11-12-19-17)16-9-5-2-6-10-16/h1-10H,11-14H2,(H,18,19)/p+1

Synthetic route

antazoline hydrochloride (2508-72-7) → 4-nitrobenzyl nitrate (15539-77-2) + picramide (489-98-5) + N,2,4,6-Tetranitro-N-(2-nitrobenzyl)-anilin (95711-93-6) + N,2,4,6-Tetranitro-N-(3-nitrobenzyl)-anilin (95711-94-7) + N,2,4,6-Tetranitro-N-(4-nitrobenzyl)-anilin (95711-95-8) + 4-nitrobenzaldehdye (555-16-8)

Conditions	Yield
With nitric acid Product distribution;

Downstream Products

• 15539-77-2 4-nitrobenzyl nitrate 
• 489-98-5 picramide 
• 95711-93-6 N,2,4,6-Tetranitro-N-(2-nitrobenzyl)-anilin 
• 95711-94-7 N,2,4,6-Tetranitro-N-(3-nitrobenzyl)-anilin 
• 95711-95-8 N,2,4,6-Tetranitro-N-(4-nitrobenzyl)-anilin 
• 555-16-8 4-nitrobenzaldehdye