Amezinium metilsulfate (

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, trade name Regulton) is a sympathomimetic drug used for the treatment of low

blood pressure Blood pressure (BP) is the pressure of Circulatory system, circulating blood against the walls of blood vessels. Most of this pressure results from the heart pumping blood through the circulatory system. When used without qualification, the term ...

. It has multiple mechanisms, including stimulation of

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and beta-1 receptors and inhibition of

noradrenaline Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as a hormone, neurotransmitter and neuromodulator. The name "noradrenaline" (from ...

and

tyramine Tyramine ( ) (also spelled tyramin), also known under several other names, is a naturally occurring trace amine derived from the amino acid tyrosine. Tyramine acts as a catecholamine releasing agent. Notably, it is unable to cross the bl ...

uptake.

Synthesis

This antidepressant is made from Chloridazon starting material. Amezinium metilsulfate synthesis

The halogenation of 2-Butyne-1,4-diol 10-65-6(1) with chlorine gives Mucochloric acid 7-56-9(2). Treatment with Phenylhydrazine 00-63-0(3) gives 1-Phenyl-4,5-dichloro-6-pyridazone 698-53-9(4). Addition of ammonia leads to Chloridazon 698-60-8(5). Catalytic hydrogenation yields 5-amino-2-phenylpyridazin-3-one 3589-77-0(6). Alkylation with dimethyl sulfate completed the synthesis of Amezinium metisulfate (7).

References

Antihypotensive agents Pyridazines Methyl esters {{cardiovascular-drug-stub