10563-70-9

Crystalline Solid

Trausabun,Lusofarma,W. Germany,1965

Antidepressant

ChEBI: Melitracen hydrochloride is a member of anthracenes.

24 g of 2-o-benzoylphenylpropanol-2 (MP 116°C) were dissolved in 250 ml of anhydrous ether and the resulting solution was added dropwise while stirring to a suspension of 0.22 mol of dimethylaminopropylmagnesium chloride in 100 ml of ether. The reaction mixture was refluxed for one hour on a steam bath, and water and dilute hydrochloric acid were added until the reaction was pH 4-5. The aqueous phase was separated and 60 ml of concentrated aqueous ammonia were added. The mixture was extracted with ether, and the ether phase was separated, dried and evaporated in a steam bath. The residue was dissolved in hot petroleum ether and the solution left standing to cool for some time, whereupon 4-dimethylamino-1-phenyl-1-[2-(2-hydroxy-2- propyl)phenyl]-butanol-1 crystallized out as white crystals which were sucked off. After drying they melted at 88°C to 90°C.
10 g of this compound were cautiously dissolved in 50 ml of concentrated sulfuric acid under cooling and the mixture was kept at room temperature for 24 hours, whereupon the reaction mixture was poured into 200 g of finely crushed ice, and concentrated aqueous ammonia was added to about pH 9, whereupon the oil which separated out was extracted with ether. The ether phase was separated, dried and the ether evaporated on a steam bath. The residue was dissolved in 20 ml of acetone and the solution neutralized with a solution of dry hydrogen chloride in ether. The white crystals of 9-γdimethylaminopropylidene-10,10-dimethyl-9,10-dihydroanthracene hydrochloride which separated out was filtered off and dried. Yield 9 g. MP 245°C to 247°C.

Antidepressant

Melitracen is a tricyclic antidepressant (TCA) th at likely exerts its in vivo efficacy similarly as imipramine and amitriptyline by inhibiting serotonin-norepinephrine reuptake.