56775-88-3

Tan Oil

Serotonin uptake inhibitor. Antidepressant

5-HT re-uptake inhibitor; selective over noradrenalin and dopamine uptake (IC 50 values are 0.33, 8.2 and 12 μ M respectively). Modulates nociception and induces hyperglycemia in vivo , and is an orally active antidepressant.

Normud ,Astra ,W. Germany ,1981

ChEBI: Zimeldine is a member of styrenes.

To 9 g of n-butyl lithium in 200 ml of dry ether 20 g of 3-bromopyridine is added as quickly as possible at -40°C without raising the temperature. When the addition is finished the mixture is stirred for another 30 minutes. Thereafter 32.5 g of ω-dimethylamino-4'-bromopropiophenone is added in such a way that the temperature does not exceed -40°C. The cooling is discontinued and the mixture is stirred during the night whereupon the reaction mixture is poured onto ice and diluted HCl, which is washed with ether and is extracted with 20 ml of methylene dichloride. The methylene dichloride is dried and evaporated. The crystals are dissolved in water, which then is made alkaline with a solution of Na 2 CO 3 , is extracted with ether, dried, and evaporated and recrystallized from isopropyl ether, petroleum ether 1:1. Yield 4 g of 1-(4'-bromophenyl)-3-(N,N-dimethylamino)-1-(3''-pyridyl)- propanol. Melting point 67°C.
3.6 g of 1-(4'-bromophenyl)-3-(N,N-dimethylamino)-1-(3''-pyridyl)-propanol are dissolved in 15 ml of 85% H 2 SO 4 and heated at 170°C for 10 minutes. The reaction mixture is poured into 60 ml of water, which is then made alkaline with 10 N NaOH, and is extracted with 2 x 25 ml of ether. The ether is dried with Na 2 SO 4 , treated with active carbon and evaporated. The residue is dissolved in 25 ml of acetone and an equivalent amount of oxalic acid dissolved in 25 ml of acetone is added. The precipitate obtained is filtered off, is dissolved in 50 ml of water, which is made alkaline with 10 N NaOH and is extracted with 2 x 25 ml of ether. The ether solution is dried with Na 2 SO 4 and is filtered, whereupon dry HCl is introduced. The precipitate obtained is filtered off. Yield 1.2 g of 3-(4'-bromophenyl)-3-(3''-pyridyl)- dimethylallylamine dihydrochloride (H 102/09). Melting point 193°C.

Normid;Normud;Zelmidine.

Antidepressant

Zimeldine, an inhibitor of serotonin uptake, was introduced in 1982 for the treatment of depressive illness. By 1983 its use had been associated with incidences of hypersensitivity of varying severity and serious neurological side effects including the Guillain-Barr, syndrome. Following discussions with the National Board of Health and Welfare of Sweden, the major manufacturer decided to withdraw the drug on a worldwide basis.