Methapyrilene

Methapyrilene
Clinical data
ATC code	R06AC05 (WHO) ;
Identifiers
	IUPAC name N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine;
CAS Number	91-80-5 ;
PubChem CID	4098;
DrugBank	DB04819 ;
ChemSpider	3956 ;
UNII	A01LX40298;
KEGG	C11114 ;
ChEBI	CHEBI:6820 ;
CompTox Dashboard (EPA)	DTXSID2023278 ;
Chemical and physical data
Formula	C14H19N3S
Molar mass	261.387 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES n1ccccc1N(CCN(C)C)Cc2sccc2;
	InChI InChI=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 ; Key:HNJJXZKZRAWDPF-UHFFFAOYSA-N ;
	(verify)

"Thionylan" redirects here. The thionyl halides should not be confused with "thionylan" and include thionyl fluoride, thionyl chloride, and thionyl bromide.

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.^[1] 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 when methapyrilene was demonstrated to cause liver cancer in rats when given chronically.^[2]

Synthesis

References

^ http://www.thefreelibrary.com/Archive.-a0119048413
^ http://www.ncbi.nlm.nih.gov/pubmed/7403848
^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01186a023, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01186a023 instead.

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[1] ttp://www.thefreelibrary.com/Archive.-a0119048413

[2] ttp://www.ncbi.nlm.nih.gov/pubmed/7403848

[3] Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01186a023, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with |doi=10.1021/ja01186a023 instead.

[1]

[2]

[3]

v t e Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine

Synthesis

See also

References