Methapyrilene

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

Methapyrilene

Systematic (IUPAC) name
N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine
Identifiers
CAS Number	91-80-5
ATC code	R06AC05 (WHO)
PubChem	CID 4098
DrugBank	DB04819
ChemSpider	3956
UNII	A01LX40298
KEGG	C11114
ChEBI	CHEBI:6820
Chemical data
Formula	C14H19N3S
Molar mass	261.387 g/mol
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
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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]

See also

• Thenalidine
• Methaphenilene

References

1. The Birmingham Post Archive. thefreelibrary.com
2. Lijinsky, W; Reuber, M.; Blackwell, B. (1980). "Liver tumors induced in rats by oral administration of the antihistaminic methapyrilene hydrochloride". Science 209 (4458): 817–819. doi:10.1126/science.7403848. PMID 7403848.