Methapyrilene

Methapyrilene
Clinical data
ATC code	R06AC05 (WHO) ;
Identifiers
	IUPAC name N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine;
CAS Number	91-80-5 ;
PubChem CID	4098;
DrugBank	DB04819 ;
ChemSpider	3956 ;
UNII	A01LX40298;
KEGG	C11114 ;
ChEBI	CHEBI:6820 ;
CompTox Dashboard (EPA)	DTXSID2023278 ;
Chemical and physical data
Formula	C14H19N3S
Molar mass	261.39 g·mol−1
3D model (JSmol)	Interactive image;
	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.^[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.^[2] All of these products were reformulated in the late 1970s^[3] when methapyrilene was demonstrated to cause liver cancer in rats when given chronically.^[4]

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[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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[1] [1]
"Archive". Birmingham Post. July 1979 – via The Free Library.

[2] [2]
"FDA Seeks Restrictions On Sleeping Aid Drugs". Daily Press. Vol. 83, no. 164. 1978-06-13. p. 1 – via Newspapers.com.

[3] [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] [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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Methapyrilene

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References

Clinical data

ATC code	R06AC05 (WHO)
Identifiers
IUPAC name N,N-dimethyl-N'-pyridin-2-yl-N'-(2-thienylmethyl)ethane-1,2-diamine
CAS Number	91-80-5^Y
PubChem CID	4098
DrugBank	DB04819^Y
ChemSpider	3956^Y
UNII	A01LX40298
KEGG	C11114^Y
ChEBI	CHEBI:6820^Y
CompTox Dashboard (EPA)	DTXSID2023278
Chemical and physical data
Formula	C₁₄H₁₉N₃S
Molar mass	261.39 g·mol⁻¹
3D model (JSmol)	Interactive image
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^Y Key:HNJJXZKZRAWDPF-UHFFFAOYSA-N^Y
(verify)