108929-04-0

Basic information

• Product Name: EPINASTINE HYDROCHLORIDE
• Synonyms: f)imidazo(1,5-a)azepin-3-amine,9,13b-dihydro-ih-dibenz(hydrochloride;EPINASTINE HCL;EPINASTIN HCL;3-AMINO-9,13B-DIHYDRO-1H-DIBENZ[C,F]IMIDAZO[1,5-A]AZEPINE HYDROCHLORIDE;WAL-801CL;9,13b-Dihydro-1H-Dibenz[c,f]imidazo[1,5-α]azepin-3-amine Hydrochloride;Alesion;Elestat
• CAS NO: 108929-04-0
• Molecular Formula: C₁₆H₁₅N₃*ClH
• Molecular Weight: 285.77
• EINECS: 1312995-182-4
• Product Categories: Antihistaminic;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Inhibitors
• Mol File: 108929-04-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 273-275°C
• Boiling Point: 428 °C at 760 mmHg
• Flash Point: 212.7 °C
• Appearance: white/
• Density: 1.32g/cm3
• Vapor Pressure: 1.56E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: soluble38mg/mL
• CAS DataBase Reference: EPINASTINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: EPINASTINE HYDROCHLORIDE(108929-04-0)
• EPA Substance Registry System: EPINASTINE HYDROCHLORIDE(108929-04-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: HO4360000
• Hazardous Substances Data: 108929-04-0(Hazardous Substances Data)

Usage

Description

Epinastine Hydrochloride is a tetracyclic, non-sedating histamine H1 receptor antagonist with antihistaminic properties. It is a white crystalline solid that is used in various applications due to its ability to block histamine receptors, which can help alleviate symptoms associated with histamine release.

Uses

Used in Pharmaceutical Industry:
Epinastine Hydrochloride is used as an antihistamine for treating allergic symptoms such as itching, redness, and swelling. Its non-sedating nature makes it suitable for use during the day without causing drowsiness.
Used in Ophthalmology:
In the field of ophthalmology, Epinastine Hydrochloride is used as an anti-allergic agent for the treatment of ocular conditions such as conjunctivitis and eye inflammation. Its ability to block histamine receptors helps reduce itching and redness in the eyes.
Used in Dermatology:
Epinastine Hydrochloride is also used in dermatology as a topical treatment for various skin conditions, including atopic dermatitis, urticaria, and other allergic skin reactions. Its antihistaminic properties help to alleviate itching, redness, and inflammation associated with these conditions.
Used in Veterinary Medicine:
In veterinary medicine, Epinastine Hydrochloride is used as an antihistamine to treat allergic reactions in animals, such as itching and inflammation due to insect bites, food allergies, or other environmental factors. Its non-sedating properties make it a suitable choice for use in pets without causing excessive drowsiness.

Biochem/physiol Actions

Epinastine hydrochloride is a non-sedating H1 histamine receptor antagonist.

InChI:InChI=1/C16H15N3.ClH/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16;/h1-8,15H,9-10H2,(H2,17,18);1H

Upstream product

• 706753-75-5 9H-dibenzo[c,f]imidazo[1,5-a]azepin-3-amine 
• 21535-43-3 N-[2-(phenylmethyl)phenyl]-2-chloroacetamide 
• 80012-79-9 6-aminomethyl-6,11-dihydro-5H-dibenzo[b,e]azepine maleate 
• 28059-64-5 2-benzylaniline 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 506-68-3 bromocyane 
• 41218-84-2 6-aminomethyl-6,11-dihydro-5H-dibenzo[b,e]azepine 
• 80012-43-7 epinastine 
• 80012-69-7 11H-dibenzazepine-6-carbonitrile 
• 4998-12-3 6-chloro-11H-dibenzazepine 
• 127786-29-2 3-amino-9,13b-dihydro-1H-dibenzimidazo<1,5-a>azepine hydrobromide 

Relevant articles and documents

A facile synthesis of epinastine HCl via dehydroepinastine intermediate

Epinastine is a second generation histamine H1 receptor antagonist used as a non-sedative antiallergic drug. When given orally, epinastine poorly penetrates blood-brain barrier (BBB) and appears to be free of cardiac toxicity as compared to other antihistamine drugs. A couple of synthetic approaches for epinastine HCl have been reported so far. They hold several problems such as explosive, highly toxic or expensive reagents. Moreover, they usually do not offer concise synthetic steps. In our synthesis shown here, a commonly used starting material, 6-(chloromethyl)-11H-dibenzo[b,e]azepine is treated with cyanamide to afford dehydroepinastine (14) in significantly high yield, which is subsequently reduced in the presence of aqueous HCl to give epinastine HCl in only two steps (75% overall yield for two steps). The problems associated with the reported processes such as using toxic and dangerous chemicals, lengthy synthetic steps or low overall product yields can be overcome by utilizing this new route. We believe our synthetic scheme might provide a breakthrough to reduce the cost of the production of epinastine HCl.

A synthesis method of epinastine hydrochloride

The invention discloses a synthesis method for epinastine hydrochloride. With a compound (6-aminomethyl-6,11-dihydro-5H-dibenzo [b, e] azepine maleate), shown in the formula II, being the initial raw material, epinastine hydrochloride is synthesized. By the utilization of the synthesis method for epinastine hydrochloride, epinsastine hydrochloride can be effectively synthesized, and the method has the advantages of being high in synthesis efficiency, safe in production, simple in technology operation, short in production period and the like and is more suitable for large-scale and industrialized production of epinastine hydrochloride.

Synthetic method of epinastine hydrochloride

The invention discloses a synthetic method of epinastine hydrochloride. The synthetic method comprises the following steps: enabling a substance A to react with a substance B to obtain a substance C; enabling the substance C to be subjected to ring closing reaction with polyphosphoric acid to obtain a substance D; enabling the substance D to react with a de-protection reagent to obtain a substance E; enabling the substance E to react with cyanogen bromide to obtain epinastine and then salifying with hydrochloric acids to obtain the epinastine hydrochloride. The synthetic method disclosed by the invention is easily-available in raw materials, mild in reaction conditions, low in energy consumption, low in production cost, simple to operate, short in preparation period and suitable for large-scale industrial production; the prepared epinastine hydrochloride is high in purity and relatively high in yield in each step of reaction.