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Methapyrilene

Summary

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]

Methapyrilene
Clinical data
ATC code
Identifiers
  • N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine
CAS Number
  • 91-80-5 checkY
PubChem CID
  • 4098
DrugBank
  • DB04819 checkY
ChemSpider
  • 3956 checkY
UNII
  • A01LX40298
KEGG
  • C11114 checkY
ChEBI
  • CHEBI:6820 checkY
CompTox Dashboard (EPA)
  • DTXSID2023278 Edit this at Wikidata
Chemical and physical data
FormulaC14H19N3S
Molar mass261.39 g·mol−1
3D model (JSmol)
  • Interactive image
  • n1ccccc1N(CCN(C)C)Cc2sccc2
  • 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
  (verify)

See also edit

References edit

  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.