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{{Short description|Chemical compound}}
{{Unreferenced stub|auto=yes|date=December 2009}}
{{hatnote|"Thionylan" redirects here. Not to be confused with thionyl halides: [[thionyl fluoride]], [[thionyl chloride]] and [[thionyl bromide]].}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 400306518
| verifiedrevid =
| IUPAC_name = ''N'',''N''-dimethyl-''N<nowiki>'</nowiki>''-pyridin-2-yl-''N<nowiki>'</nowiki>''-(2-thienylmethyl)ethane-1,2-diamine
| IUPAC_name = ''N'',''N''-dimethyl-''N<nowiki>'</nowiki>''-pyridin-2-yl-''N<nowiki>'</nowiki>''-(2-thienylmethyl)ethane-1,2-diamine
| image = Methapyrilene.svg
| image = Methapyrilene.svg
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 91-80-5
| CAS_number = 91-80-5
| ATC_prefix = R06
| ATC_prefix = R06
| ATC_suffix = AC05
| ATC_suffix = AC05
| PubChem = 4098
| PubChem = 4098
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite||drugbank}}
| DrugBank = DB04819
| DrugBank = DB04819
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 3956
| ChemSpiderID = 3956
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite||FDA}}
| UNII = A01LX40298
| UNII = A01LX40298
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite||kegg}}
| KEGG = C11114
| KEGG = C11114
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite||EBI}}
| ChEBI = 6820
| ChEBI = 6820


<!--Chemical data-->
<!--Chemical data-->
| C=14 | H=19 | N=3 | S=1
| C=14 | H=19 | N=3 | S=1
| molecular_weight = 261.387
| smiles = n1ccccc1N(CCN(C)C)Cc2sccc2
| smiles = n1ccccc1N(CCN(C)C)Cc2sccc2
| 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
| InChIKey = HNJJXZKZRAWDPF-UHFFFAOYAC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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
| 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
Line 48: Line 46:
| StdInChIKey = HNJJXZKZRAWDPF-UHFFFAOYSA-N
| StdInChIKey = HNJJXZKZRAWDPF-UHFFFAOYSA-N
}}
}}
'''Methapyrilene''' is an [[antihistamine]] and [[anticholinergic]] of the [[pyridine]] [[chemical class]] 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=[[Birmingham Post]] |via=[[The Free Library]]}}</ref> It has relatively strong [[sedative]] effects, to the extent that its primary use was as a medication for [[insomnia]] rather than for its antihistamine action. Together with [[Hyoscine hydrobromide|scopolamine]], it was the main ingredient in [[Sominex]], 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=[[Daily Press (Virginia)|Daily Press]] |via=[[Newspapers.com]] |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=[[Star Tribune|The Minneapolis Star]] |via=[[Newspapers.com]] |pages=[https://www.newspapers.com/newspage/191023340/ 1A], [https://www.newspapers.com/newspage/191023631/ 6A]}}</ref> when methapyrilene was demonstrated to cause [[liver cancer]] 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 = [[Science (journal)|Science]] | volume = 209 | issue = 4458 | pages = 817–819 | date = August 1980 | pmid = 7403848 | doi = 10.1126/science.7403848 | bibcode = 1980Sci...209..817L }}</ref>

'''Methapyrilene''' is a [[antihistamine]] and [[anticholinergic]] of the [[pyridine]] [[chemical class]] which was developed in the early 1950s. It has relatively strong [[sedative]] effects, to the extent that its primary use was as a medication for [[insomnia]] rather than for its antihistamine action. Together with [[scopolamine]], 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 [[liver cancer]] in rats when given chronically.


== See also ==
== See also ==
* [[Scopolamine]]
*[[]]
*[[Methaphenilene]]


== References ==
== References ==
{{Reflist|2}}
{{Reflist}}



{{Hypnotics}}
{{Hypnotics}}
{{Antihistamines}}
{{Cholinergics}}
{{Cholinergics}}
{{Histaminergics}}
{{Histaminergics}}


[[Category:]]


[[Category:Sedatives]]
[[Category:Sedatives]]
[[Category:Pyridines]]
[[Category:Thiophenes]]
[[Category:Thiophenes]]
[[Category:Amines]]
[[Category:]]
[[Category:H1 receptor antagonists]]
[[Category:H1 receptor antagonists]]
[[Category:Dimethylamino compounds]]



{{respiratory-system-drug-stub}}
{{respiratory-system-drug-stub}}
{{sedative-stub}}
{{sedative-stub}}

[[th:เมตทาไพริลีน]]