Amezinium metilsulfate explained

Amezinium metilsulfate (INN, trade name Regulton) is a sympathomimetic drug used for the treatment of low blood pressure. It has multiple mechanisms, including stimulation of alpha and beta-1 receptors and inhibition of noradrenaline and tyramine uptake.[1] [2]

Synthesis

This antidepressant is made from Chloridazon starting material.The halogenation of 2-Butyne-1,4-diol [110-65-6] (1) with chlorine gives Mucochloric acid [87-56-9] (2). Treatment with Phenylhydrazine [100-63-0] (3) gives 1-Phenyl-4,5-dichloro-6-pyridazone [1698-53-9] (4). Addition of ammonia leads to Chloridazon [1698-60-8] (5). Catalytic hydrogenation yields 5-amino-2-phenylpyridazin-3-one [13589-77-0] (6). Alkylation with dimethyl sulfate completed the synthesis of Amezinium metisulfate (7).

Notes and References

  1. Araújo D, Caramona MM, Osswald W . On the mechanism of action of amezinium methylsulphate on the dog saphenous vein . European Journal of Pharmacology . 90 . 2–3 . 203–14 . June 1983 . 6873182 . 10.1016/0014-2999(83)90238-8 .
  2. Lenke D, Gries J, Kretzschmar R . Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action . Arzneimittel-Forschung . 31 . 9a . 1558–65 . 1981 . 7197970 .