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methapyrilene
Sign in to saveMethapyrilene 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 liv
Chemical data
- Formula
- C14H19N3S
- Molecular weight
- 261.39 g/mol
- IUPAC name
- N,N-dimethyl-N'-pyridin-2-yl-N'-(thiophen-2-ylmethyl)ethane-1,2-diamine
- SMILES
- CN(C)CCN(CC1=CC=CS1)C2=CC=CC=N2
- InChIKey
- HNJJXZKZRAWDPF-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 47.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
269 papers- Methapyrilene toxicity.Clinical toxicology · 1977
- In vitro proteomic analysis of methapyrilene toxicity in rat hepatocytes reveals effects on intermediary metabolism.Archives of toxicology · 2019
- Methapyrilene hepatotoxicity is associated with oxidative stress, mitochondrial disfunction and is prevented by the Ca2+ channel blocker verapamil.Toxicology · 1998
- Methapyrilene kinetics and dynamics.Clinical pharmacology and therapeutics · 1981
- Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation.Chemico-biological interactions · 2000
via PubMed
Wikidata facts
- Subclass of
- pyridine alkaloid
- Mass
- 261.129968608
Show 4 more facts
- found in taxon
- Thermopsis alterniflora
- canonical SMILES
- CN(C)CCN(Cc1cccs1)c2ccccn2
- chemical formula
- C₁₄H₁₉N₃S
- Commons category
- Methapyrilene
Sources (2)
via Wikidata · CC0
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Encyclopedic overview
2 sectionsContents
- See also
- References
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 == Thenalidine Methaphenilene
Excerpted from Wikipedia’s “methapyrilene” article, available under the CC BY-SA 4.0 licence.
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