| Revision as of 15:02, 21 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'CAS_number').← Previous edit |
Latest revision as of 07:17, 23 December 2024 edit undoBoghog (talk | contribs)Autopatrolled, Extended confirmed users, IP block exemptions, New page reviewers, Pending changes reviewers, Rollbackers, Template editors137,751 edits templated cites; removed patent citations (unreliable sources) |
| (17 intermediate revisions by 16 users not shown) |
| Line 1: |
Line 1: |
|
|
{{Short description|Chemical compound}} |
|
{{Drugbox |
|
{{Drugbox |
|
| Verifiedfields = changed |
|
| Verifiedfields = changed |
|
⚫ |
| verifiedrevid = 456687368 |
|
| Watchedfields = changed |
|
| ⚫ |
| verifiedrevid = 399504585 |
|
|
| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate |
|
| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate |
|
| image = Amezinium metilsulfate.png |
|
| image = Structural formula of amezinium metilsulfate.svg |
|
|
|
|
|
<!--Clinical data--> |
|
<!--Clinical data--> |
| Line 27: |
Line 27: |
|
|
|
|
|
<!--Identifiers--> |
|
<!--Identifiers--> |
|
|
| CAS_number_Ref = {{cascite|changed|??}} |
|
| CAS_number = <!-- blanked - oldvalue: 30578-37-1 --> |
|
| CAS_number = 30578-37-1 |
|
| ATC_prefix = C01 |
|
| ATC_prefix = C01 |
|
| ATC_suffix = CA25 |
|
| ATC_suffix = CA25 |
|
| ATC_supplemental = |
|
| ATC_supplemental = |
|
| PubChem = 71926 |
|
| PubChem = 71926 |
|
|
| ChEBI = 31201 |
|
|
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
|
|
| ChEMBL = 2106667 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank = |
|
| DrugBank = |
| Line 37: |
Line 41: |
|
| ChemSpiderID = 64937 |
|
| ChemSpiderID = 64937 |
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
| UNII_Ref = {{fdacite|changed|FDA}} |
|
| UNII = <!-- blanked - oldvalue: 03NR868ICX --> |
|
| UNII = 03NR868ICX |
|
| KEGG_Ref = {{keggcite|changed|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = D01304 |
|
| KEGG = D01304 |
|
|
|
|
| Line 44: |
Line 48: |
|
| chemical_formula = |
|
| chemical_formula = |
|
| C=12 | H=15 | N=3 | O=5 | S=1 |
|
| C=12 | H=15 | N=3 | O=5 | S=1 |
|
| molecular_weight = 313.32 g/mol |
|
|
| smiles = COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O) |
|
| smiles = COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O) |
|
| InChI = 1/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) |
|
|
| InChIKey = ZEASXVYVFFXULL-UHFFFAOYAG |
|
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 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) |
|
| StdInChI = 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) |
| Line 54: |
Line 55: |
|
}} |
|
}} |
|
|
|
|
|
'''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>{{pmid|6873182}}</ref><ref>{{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> |
|
|
|
|
|
==References== |
|
==Synthesis== |
|
|
This antidepressant is made from ] starting material. |
|
|
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). |
|
|
|
|
|
== References == |
|
{{reflist}} |
|
{{reflist}} |
|
|
|
|
|
{{Cardiac stimulants excluding cardiac glycosides}} |
|
{{Cardiac stimulants excluding cardiac glycosides}} |
|
|
|
|
|
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
|
|
|
|
{{cardiovascular-drug-stub}} |
|
{{cardiovascular-drug-stub}} |
|
|
|
|
] |
|