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Revision as of 12:02, 29 November 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: StdInChI StdInChIKey.← 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 editors137,946 edits templated cites; removed patent citations (unreliable sources)
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			{{Short description|Chemical compound}}
	{{Drugbox		{{Drugbox
			| Verifiedfields = changed
⚫	| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
			| verifiedrevid = 456687368
	| image = Amezinium metilsulfate.png
		⚫	| IUPAC_name = 6-Methoxy-1-phenylpyridazin-1-ium-4-amine; methyl sulfate
			| image = Structural formula of amezinium metilsulfate.svg
			<!--Clinical data-->
			| tradename =
			| Drugs.com = {{drugs.com|international|amezinium-metilsulfate}}
		⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
		⚫	| pregnancy_US = <!-- A / B / C / D / X -->
		⚫	| pregnancy_category =
		⚫	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
		⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
		⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
		⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
		⚫	| legal_status = Rx-only
		⚫	| routes_of_administration = Oral
			<!--Pharmacokinetic data-->
		⚫	| bioavailability =
		⚫	| protein_bound =
		⚫	| metabolism =
		⚫	| elimination_half-life =
		⚫	| excretion =
			<!--Identifiers-->
			| CAS_number_Ref = {{cascite|changed|??}}
		⚫	| CAS_number = 30578-37-1
		⚫	| ATC_prefix = C01
		⚫	| ATC_suffix = CA25
		⚫	| ATC_supplemental =
		⚫	| PubChem = 71926
			| ChEBI = 31201
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 2106667
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
		⚫	| DrugBank =
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 64937		| ChemSpiderID = 64937
			| UNII_Ref = {{fdacite|changed|FDA}}
	| 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)
			| UNII = 03NR868ICX
	| InChIKey = ZEASXVYVFFXULL-UHFFFAOYAG
			| KEGG_Ref = {{keggcite|correct|kegg}}
	| smiles1 = S(=O)(=O)OC.O(c1(ncc(N)c1)c2ccccc2)C
			| KEGG = D01304
			<!--Chemical data-->
		⚫	| chemical_formula =
		⚫	| C=12 | H=15 | N=3 | O=5 | S=1
		⚫	| smiles = COC1=(N=CC(=C1)N)C2=CC=CC=C2.COS(=O)(=O)
			| 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)
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = ZEASXVYVFFXULL-UHFFFAOYSA-N		| StdInChIKey = ZEASXVYVFFXULL-UHFFFAOYSA-N
⚫	| CAS_number = 30578-37-1
	| CAS_supplemental =
⚫	| ATC_prefix = none
⚫	| ATC_suffix =
⚫	| ATC_supplemental =
⚫	| PubChem = 71926
⚫	| DrugBank =
⚫	| chemical_formula =
⚫	| 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)
⚫	| bioavailability =
⚫	| protein_bound =
⚫	| metabolism =
⚫	| elimination_half-life =
⚫	| excretion =
⚫	| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
⚫	| pregnancy_US = <!-- A / B / C / D / X -->
⚫	| pregnancy_category=
⚫	| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
⚫	| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
⚫	| legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
⚫	| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
⚫	| legal_status = Rx-only
⚫	| routes_of_administration = Oral
	}}		}}
			'''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''' (]) is a sympathomimetic drug.
			==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 ==
	{{pharma-stub}}
			{{reflist}}
			{{Cardiac stimulants excluding cardiac glycosides}}
			]
	]		]
			]
			{{cardiovascular-drug-stub}}