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'''Amezinium metilsulfate''' (], trade name '''Regulton''') is a ] drug used for the treatment of low ]. It has multiple mechanisms, including stimulation of ] and ]s and inhibition of ] and ] uptake.<ref>{{cite journal | vauthors = Araújo D, Caramona MM, Osswald W | title = On the mechanism of action of amezinium methylsulphate on the dog saphenous vein | journal = European Journal of Pharmacology | volume = 90 | issue = 2–3 | pages = 203–14 | date = June 1983 | pmid = 6873182 | doi = 10.1016/0014-2999(83)90238-8 }}</ref><ref>{{cite journal | vauthors = Lenke D, Gries J, Kretzschmar R | title = Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action | journal = Arzneimittel-Forschung | volume = 31 | issue = 9a | pages = 1558–65 | year = 1981 | pmid = 7197970 }}</ref> '''Amezinium metilsulfate''' (], trade name '''Regulton''') is a ] drug used for the treatment of low ]. It has multiple mechanisms, including stimulation of ] and ]s and inhibition of ] and ] uptake.<ref>{{cite journal | vauthors = Araújo D, Caramona MM, Osswald W | title = On the mechanism of action of amezinium methylsulphate on the dog saphenous vein | journal = European Journal of Pharmacology | volume = 90 | issue = 2–3 | pages = 203–14 | date = June 1983 | pmid = 6873182 | doi = 10.1016/0014-2999(83)90238-8 }}</ref><ref>{{cite journal | vauthors = Lenke D, Gries J, Kretzschmar R | title = Pharmacology of amezinium, a novel antihypotensive drug. III. Studies on the mechanism of action | journal = Arzneimittel-Forschung | volume = 31 | issue = 9a | pages = 1558–65 | year = 1981 | pmid = 7197970 }}</ref>

==Synthesis== ==Synthesis==
This antidepressant is made from ] starting material. This antidepressant is made from ] starting material.
Synthesis:<ref>Unterhalt, B.; Amezinium metilsulfate. Drugs Fut 1981, 6, 4, 207.</ref><ref>{{Cite journal |last=Reicheneder |first=F. |last2=Burger |first2=T. F. |last3=König |first3=H. |last4=Kropp |first4=R. |last5=Lietz |first5=H. |last6=Thyes |first6=M. |last7=Wiersdorff |first7=W. W. |date=1981 |title=Amezinium. Synthesis and radioactive labelling |url=https://pubmed.ncbi.nlm.nih.gov/7197967 |journal=Arzneimittel-Forschung |volume=31 |issue=9a |pages=1529–1533 |issn=0004-4172 |pmid=7197967}}</ref><ref>Beljean, M.; et al.; Synthse de drivs hydrazino et hydrazones dans la srie des thiazolopyridazinos-7. Bull Soc Chim France 1973, 3324.</ref> Patents:<ref>Walter-Wielant Dr. Wiersdorff, Rudolf Kropp, EP0063267 (1982 to BASF Aktiengesellschaft).</ref><ref>Rudolf Kropp, Franz Reicheneder, US3631038 (1971 to Basf Ag).</ref>]] Synthesis:<ref>{{cite journal | vauthors = Unterhalt B | title = Amezinium metilsulfate | journal = Drugs of the Future | date = 1981 | volume = 6 | issue = 4 | pages = 207 | doi = 10.1358/dof.1981.006.04.199346 }}</ref><ref>{{cite journal | vauthors = Reicheneder F, Burger TF, König H, Kropp R, Lietz H, Thyes M, Wiersdorff WW | title = Amezinium. Synthesis and radioactive labelling | journal = Arzneimittel-Forschung | volume = 31 | issue = 9a | pages = 1529–1533 | date = 1981 | pmid = 7197967 }}</ref><ref>{{cite journal | vauthors = Beljean M, Pays M | title = Heterocyclic hydrazines and hydrazones. II. Synthesis of hydrazino derivatives and of hydrazones in the thiazolopyridazin-7-ones | journal = Bulletin de la Societe Chimique de France | volume = 12 | issue = 2 | pages = 3324–3330 }}</ref>]]
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 completed the synthesis of Amezinium metisulfate (7). 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 completed the synthesis of Amezinium metisulfate (7).


Latest revision as of 07:17, 23 December 2024

Chemical compound Pharmaceutical compound
Amezinium metilsulfate
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.045.665 Edit this at Wikidata
Chemical and physical data
FormulaC12H15N3O5S
Molar mass313.33 g·mol
3D model (JSmol)
SMILES
  • COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=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)
  • Key:ZEASXVYVFFXULL-UHFFFAOYSA-N
  (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.

Synthesis

This antidepressant is made from Chloridazon starting material.

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 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 (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 thiazolopyridazin-7-ones". Bulletin de la Societe Chimique de France. 12 (2): 3324–3330.
Cardiac stimulants excluding cardiac glycosides (C01C)
Adrenergic and
dopaminergic agents
Adrenergic agonists
α
β
mixed
Dopamine agonists
Both
Unknown/ungrouped
Phosphodiesterase inhibitors (PDE3I)
Other cardiac stimulants
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