Amitriptyline Oxide

Trade Name Manufacturer Country Year Introduced 

Phthalic anhydride is reacted with phenylacetic acid to form 3-benzylidenephthalide which is then hydrogenated to 2-phenethylbenzoic acid. Conversion to the acid chloride followed by intramolecular dehydrochlorination yields the ketone, 5H-dibenzo[a,d] cyclohepten-5-one. The ketone undergoes a Grignard reaction with 3-(dimethylamino)propyl chloride to give 5-(7-dimethylaminopropylidene)-5H-dibenzo[a,d] cycloheptene. 

Chemical Name 3-(3 -Dimethylaminopropylidene)dibenzo [a,d] cyclohepta-1,4-diene N-oxide 

3 g (0.1 mol) of 3-(3 -dimethylaminopropylidene)dibenzo[a,d] cyclohepta-1,4-diene hydrochloride are dissolved in water, and the free base is liberated by means of a 28% aqueous solution of sodium hydroxide. The free base is sucked off, washed with water, and dissolved in 100 ml of methanol. To the solution are added 31 ml of 30% hydrogen peroxide. After 7 days, the reaction mixture is diluted with 200 ml of water, and the major part of the methanol Is evaporated in vacuum. The precipitated N-oxide crystals are filtered off, washed with water, and dried, yielding 27 g of the dihydrate of 3-(3 -dimethylaminopropylidene)dibenzo-[a,d] cyclohepta-1,4-diene N-oxide with melting point of 102° to 103°C. In dehydrated state the melting point is 228°to 230°C. 

Dibenzo[adl cyclohepta-1,4-diene-5-one 3-Dlmethylamlnopropanol Magnesium Chloride Hydrogen Peroxide 

3-(Dimethylamino)propyl Chloride Hydrochloric Acid Phenylacetic Acid  

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Dibenzo[a,dlcyclohepta-1,4-diene-5-one Amitriptylin oxide Dibenzo[a,el cycloheptatrien-5-one Cyproheptadine 5H-Dibenzo (a,d 1 cycloheptene Protriptyline... 

Amitriptylin oxide 3-(Dimethylamino) propyl chloride Amitriptyline HCI Ch/orprothixene Clomipramine Cyclobenzaprine Imipramine HCI Oxetorone fumarate Prothipendyl HCI... 

Amitriptyline oxide Oxygenated ring Metabolite of amitriptyline... 

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