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Methapyrilene

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Methapyrilene
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
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UNII
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ChEBI
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Chemical and physical data
FormulaC14H19N3S
Molar mass261.39 g·mol
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
  • Key:HNJJXZKZRAWDPF-UHFFFAOYSA-N
  (verify)

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. 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.

See also

References

  1. "Archive". Birmingham Post. July 1979 – via The Free Library.
  2. "FDA Seeks Restrictions On Sleeping Aid Drugs". Daily Press. Vol. 83, no. 164. 1978-06-13. p. 1 – via Newspapers.com.
  3. Cook C (1979-06-28). "Sleep aids back with new drug | Critics assail 'human testing'". The Minneapolis Star. pp. 1A, 6A – via Newspapers.com.
  4. Lijinsky W, Reuber MD, Blackwell BN (August 1980). "Liver tumors induced in rats by oral administration of the antihistaminic methapyrilene hydrochloride". Science. 209 (4458): 817–819. Bibcode:1980Sci...209..817L. doi:10.1126/science.7403848. PMID 7403848.
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