Amezinium metilsulfate

Amezinium metilsulfate

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C01CA25 ( WHO )
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
CAS Number	30578-37-1  N
PubChem CID	71926
ChemSpider	64937  Y
UNII	03NR868ICX
KEGG	D01304  Y
ChEBI	CHEBI:31201
ChEMBL	ChEMBL2106667  N
CompTox Dashboard (EPA)	DTXSID00184657
ECHA InfoCard	100.045.665
Chemical and physical data
Formula	C12H15N3O5S
Molar mass	313.33 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=[N+](N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O)[O-]
InChI InChI=1S/C11H11N3O.CH4O4S/c1-15-11-7-9(12)8-13-14(11)10-5-3-2-4-6-10;1-5-6(2,3)4/h2-8,12H,1H3;1H3,(H,2,3,4) Y Key:ZEASXVYVFFXULL-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

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 2-butyne-1,4-diol starting material with chloridazon  [ de ] as an intermediate.

Thieme ChemDrug Synthesis:

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

1. Araújo D, Caramona MM, Osswald W (June 1983). "On the mechanism of action of amezinium methylsulphate on the dog saphenous vein". European Journal of Pharmacology. 90 (2–3): 203–14. doi:10.1016/0014-2999(83)90238-8. PMID   6873182.
2. Lenke D, Gries J, Kretzschmar R (1981). "Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action". Arzneimittel-Forschung. 31 (9a): 1558–65. PMID   7197970.
3. Unterhalt B (1981). "Amezinium metilsulfate". Drugs of the Future. 6 (4): 207. doi:10.1358/dof.1981.006.04.199346.
4. Reicheneder F, Burger TF, König H, Kropp R, Lietz H, Thyes M, Wiersdorff WW (1981). "Amezinium. Synthesis and radioactive labelling". Arzneimittel-Forschung. 31 (9a): 1529–1533. PMID   7197967.
5. Beljean M, Pays M. "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. 12 (2): 3324–3330.