Amezinium metilsulfate

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]

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)

Synthesis

This antidepressant is made from Chloridazon starting material.

Thieme ChemDrug Synthesis:^[3][4][5] Patents:^[6][7]

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).

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.; Amezinium metilsulfate. Drugs Fut 1981, 6, 4, 207.
4. Reicheneder F, Burger TF, König H, Kropp R, Lietz H, Thyes M, Wiersdorff WW. Amezinium. Synthesis and radioactive labelling. Arzneimittelforschung. 1981;31(9a):1529-33. PMID: 7197967.
5. Beljean, M.; et al.; Synthse de drivs hydrazino et hydrazones dans la srie des thiazolo[4,5-d]pyridazinos-7. Bull Soc Chim France 1973, 3324.
6. Walter-Wielant Dr. Wiersdorff, Rudolf Kropp, EP0063267 (1982 to BASF Aktiengesellschaft).
7. Rudolf Kropp, Franz Reicheneder, US3631038 (1971 to Basf Ag).