Methapyrilene

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"Thionylan" redirects here. The thionyl halides should not be confused with "thionylan" and include thionyl fluoride, thionyl chloride, and thionyl bromide.
Methapyrilene
Methapyrilene.png
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E number{{#property:P628}}
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FormulaC14H19N3S
Molar mass261.387 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

Methapyrilene synthesis[3]

See also


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.
  3. Leonard, Frederick; Solmssen, Ulrich V. (1948). "2-Thenyl Substituted Diamines with Antihistaminic Activity". Journal of the American Chemical Society. 70 (6): 2064–2067. doi:10.1021/ja01186a023.



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