Methapyrilene

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"Thionylan" redirects here. Not to be confused with thionyl halides: thionyl fluoride, thionyl chloride and thionyl bromide.
Methapyrilene
Methapyrilene.svg
Clinical data
ATC code
Identifiers
IUPAC name
  • N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H19N3S
Molar mass261.39 g·mol−1
3D model (JSmol)
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 checkY
  • Key:HNJJXZKZRAWDPF-UHFFFAOYSA-N checkY
  

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[]

References[]

  1. ^ The Birmingham Post Archive. thefreelibrary.com
  2. ^ Lijinsky W, Reuber MD, Blackwell BN (August 1980). "Liver tumors induced in rats by oral administration of the antihistaminic methapyrilene hydrochloride". Science. 209 (4458): 817–9. Bibcode:1980Sci...209..817L. doi:10.1126/science.7403848. PMID 7403848.
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