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Amezinium metilsulfate

Chemical compound

Amezinium metilsulfate
Summary

Chemical compound

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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.

Synthesis

This antidepressant is made from 2-butyne-1,4-diol starting material with as an intermediate.

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The halogenation of 2-butyne-1,4-diol (1) with chlorine gives mucochloric acid (2). Treatment with phenylhydrazine (3) gives 1-phenyl-4,5-dichloro-6-pyridazone (4). Addition of ammonia leads to chloridazon (5). Catalytic hydrogenation yields 5-amino-2-phenylpyridazin-3-one (6). Alkylation with dimethyl sulfate completes the synthesis of amezinium metisulfate (7).

References

References

  1. (June 1983). "On the mechanism of action of amezinium methylsulphate on the dog saphenous vein". European Journal of Pharmacology.
  2. (1981). "Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action". Arzneimittel-Forschung.
  3. (1981). "Amezinium metilsulfate". Drugs of the Future.
  4. (1981). "Amezinium. Synthesis and radioactive labelling". Arzneimittel-Forschung.
  5. "Heterocyclic hydrazines and hydrazones. II. Synthesis of hydrazino derivatives and of hydrazones in the thiazolo[4,5-d]pyridazin-7-ones". Bulletin de la Société Chimique de France.
Wikipedia Source

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antihypotensive-agents pyridazines methyl-esters
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