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{{Short description|Chemical compound}} |
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{{Unreferenced stub|auto=yes|date=December 2009}} |
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{{hatnote|"Thionylan" redirects here. Not to be confused with thionyl halides: ], ] and ].}} |
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{{Drugbox |
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{{Drugbox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 400306518 |
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| verifiedrevid = 447612304 |
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| IUPAC_name = ''N'',''N''-dimethyl-''N<nowiki>'</nowiki>''-pyridin-2-yl-''N<nowiki>'</nowiki>''-(2-thienylmethyl)ethane-1,2-diamine |
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| IUPAC_name = ''N'',''N''-dimethyl-''N<nowiki>'</nowiki>''-pyridin-2-yl-''N<nowiki>'</nowiki>''-(2-thienylmethyl)ethane-1,2-diamine |
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| image = Methapyrilene.svg |
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| image = Methapyrilene.svg |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 91-80-5 |
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| CAS_number = 91-80-5 |
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| ATC_prefix = R06 |
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| ATC_prefix = R06 |
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| ATC_suffix = AC05 |
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| ATC_suffix = AC05 |
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| PubChem = 4098 |
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| PubChem = 4098 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04819 |
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| DrugBank = DB04819 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 3956 |
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| ChemSpiderID = 3956 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = A01LX40298 |
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| UNII = A01LX40298 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C11114 |
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| KEGG = C11114 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 6820 |
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| ChEBI = 6820 |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=14 | H=19 | N=3 | S=1 |
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| C=14 | H=19 | N=3 | S=1 |
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| molecular_weight = 261.387 |
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| smiles = n1ccccc1N(CCN(C)C)Cc2sccc2 |
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| smiles = n1ccccc1N(CCN(C)C)Cc2sccc2 |
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| InChI = 1/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3 |
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| InChIKey = HNJJXZKZRAWDPF-UHFFFAOYAC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3 |
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| StdInChI = 1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3 |
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| StdInChIKey = HNJJXZKZRAWDPF-UHFFFAOYSA-N |
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| StdInChIKey = HNJJXZKZRAWDPF-UHFFFAOYSA-N |
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}} |
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'''Methapyrilene''' is an ] and ] of the ] ] which was developed in the early 1950s. It was sold under the trade names Co-Pyronil and Histadyl EC in the UK.<ref>{{cite news |date=July 1979 |title=Archive. |url=http://www.thefreelibrary.com/Archive.-a0119048413 |work=] |via=]}}</ref> It has relatively strong ] effects, to the extent that its primary use was as a medication for ] rather than for its antihistamine action. Together with ], it was the main ingredient in ], Nytol, and Sleep-Eze. It also provided the sedative component of Excedrin PM.<ref>{{cite news |date=1978-06-13 |title=FDA Seeks Restrictions On Sleeping Aid Drugs |url=https://newspapers.com/image/233886246/ |url-access=subscription |work=] |via=] |volume=83 |issue=164 |page=1}}</ref> All of these products were reformulated in the late 1970s<ref>{{cite news | vauthors = Cook C |date=1979-06-28 |title=Sleep aids back with new drug {{!}} Critics assail 'human testing' |url=https://www.newspapers.com/image/191023340/ |url-access=subscription |work=] |via=] |pages=, }}</ref> when methapyrilene was demonstrated to cause ] in rats when given chronically.<ref>{{cite journal | vauthors = Lijinsky W, Reuber MD, Blackwell BN | title = Liver tumors induced in rats by oral administration of the antihistaminic methapyrilene hydrochloride | journal = ] | volume = 209 | issue = 4458 | pages = 817–819 | date = August 1980 | pmid = 7403848 | doi = 10.1126/science.7403848 | bibcode = 1980Sci...209..817L }}</ref> |
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'''Methapyrilene''' is a ] and ] of the ] ] which was developed in the early 1950s. It has relatively strong ] effects, to the extent that its primary use was as a medication for ] rather than for its antihistamine action. Together with ], it was the main ingredient in '''Sominex''', '''Nytol''', and '''Sleep-Eze'''. It also provided the sedative component of '''Excedrin PM'''. All of these products were reformulated in the late 1970s because methapyrilene was demonstrated to cause ] in rats when given chronically. |
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== See also == |
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== See also == |
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== References == |
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== References == |
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{{Reflist|2}} |
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{{Reflist}} |
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{{Hypnotics}} |
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{{Hypnotics}} |
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{{Antihistamines}} |
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{{Cholinergics}} |
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{{respiratory-system-drug-stub}} |
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