CLEMASTINE FUMARATE CAS 15686-51-8

Introduction：Basic information about CLEMASTINE FUMARATE CAS 15686-51-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

CLEMASTINE FUMARATE Basic information

• Product Name: CLEMASTINE FUMARATE
• Synonyms: Pyrrolidine, 2-2-(1R)-1-(4-chlorophenyl)-1-phenylethoxyethyl-1-methyl-, (2R)-;Pyrrolidine, 2-[2-[(p-chloro-α-methyl-α-phenylbenzyl)oxy]ethyl]-1-methyl-, (+)- (8CI);[2R,(+)]-2-[2-[[(R)-1-(p-Chlorophenyl)-1-phenylethyl]oxy]ethyl]-1-methylpyrrolidine;CLEMASTINE;CLEMASTINE FUMARATE SALT;CLEMASTINUM;(2R)-2-[2-[(1R)-1-(4-CHLOROPHENYLETHOXY)]ETHYL]-1-METHYL-2-PYRROLIDINE FUMARATE;(+)-(2R)-2-[2-[[(R)-p-Chloro-alpha-methyl-alpha-phenylbenzyl]oxy]ethyl]-1-methylpyrrolidine
• CAS: 15686-51-8
• MF: C21H26ClNO
• MW: 343.89
• EINECS: 239-055-2
• Product Categories: Active Pharmaceutical Ingredients
• Mol File: 15686-51-8.mol

CLEMASTINE FUMARATE Chemical Properties

• alpha: D20 +33.6° (ethanol)
• Boiling point: bp0.02 154°
• density: 1.097±0.06 g/cm3(Predicted)
• refractive index: nD22 1.5582
• form: Solid
• pka: 10.23±0.40(Predicted)
• color: White to off-white
• CAS DataBase Reference: 15686-51-8(CAS DataBase Reference)

CLEMASTINE FUMARATE Usage And Synthesis

Originator

Tavegyl,Sandoz,France,1967

Uses

Antihistaminic.

Uses

Clemastine is used for allergy symptoms, rhinites, Quinke’s edema, anaphylactic shock,hay fever, allergic dermatitis and dermatosis, and chronic eczema. Synonyms of this drugare tavegil and meclastine.

Definition

ChEBI: 2-[(2R)-1-Methylpyrrolidin-2-yl]ethanol in which the hydrogen of the hydroxy group is substituted by a 1-(4-chlorophenyl)-1-phenylethyl group (R configuration). An antihistamine with antimuscarinic and moderate sedative prperties, it is used as its fumarate salt for the symptomatic relief of allergic conditions such as rhinitis, urticaria, conjunctivitis and in pruritic (severe itching) skin conditions.

Manufacturing Process

9.9 g of α-methyl-p-chlorobenzhydrol are added to a suspension of 2.3 g ofpowdered sodamide in 30 cc of benzene. Subsequently 7.4 g of Nmethylpyrrolidyl-(2)-ethyl chloride are added and the solution is heated to theboil at reflux for 20 hours. Then shaking is first effected with water and then 4times each time with 25 cc of 2 N hydrochloric acid. The acid extracts aremade alkaline with potassium hydroxide solution while cooling strongly, andthe precipitated oil is extracted with ether. After drying of the ethereal solutionover potassium carbonate, the solvent is evaporated and the residue isfractionally distilled in a high vacuum, whereby N-methyl-2-[2'-(α-methyl-pchlorobenzhydryloxy)-ethyl]-pyrrolidine boils over at 154°C/0.02 mm Hg. Thebase is converted to the fumarate by reaction with fumaric acid.

Brand name

Tavist (Novartis);Aller-ez plus;Alogynan;Antihist-1;Arrest;Benaznyl;Clemastin fumerate syrup;Corto-tavegil;Dexa-tavegil;Fumarsutin;Licasol;Maikohist;Mallermin;Rhinergal tavegil;Tavist 1;Tavist tablets;Tavist-1;Tavist-d;Tavist-syrup.

Therapeutic Function

Antihistaminic

Clinical Use

Antihistamine:
Symptomatic relief of allergy such as hay fever, urticaria

Synthesis

Clemastine, 2-[2-[1-(4-chlorophenyl)-1-phenylethoxy]ethyl]-1-methylpyrrolidine(16.1.4), is synthesized by reacting 1-(4-chlorophenyl)-1-phenylethanol (16.1.3) with 2-(2-chlorethyl)-2-methylpyrrolidine using sodium amide as a base. The starting1-(4-chlorophenyl)-1-phenylethanol (16.1.3) is synthesized either by reacting 4-chlorobenzophenonewith methylmagnesium chloride, or by reacting 4-chloroacetophenone withphenylmagnesium bromide.

Drug interactions

Potentially hazardous interactions with other drugs
Analgesics: sedative properties increased with opioid analgesics.

Metabolism

Extensively metabolised in the liver mainly by mono- and didemethylation and glucuronide conjugation.The metabolites are mainly excreted in the urine.

CLEMASTINE FUMARATE Preparation Products And Raw materials

• Raw materials: Sodium amide-->Fumaric acid