Mepyramine

Mepyramine
Clinical data
Other names	Pyrilamine; N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
AHFS/Drugs.com	International Drug Names
MedlinePlus	a606008
ATC code	R06AC01 (WHO) D04AA02 (WHO);
Identifiers
	IUPAC name N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine;
CAS Number	91-84-9 ; 59-33-6 (maleate);
PubChem CID	4992;
IUPHAR/BPS	1227;
DrugBank	DB06691 ;
ChemSpider	4818 ;
UNII	HPE317O9TL;
KEGG	D08183 ;
ChEBI	CHEBI:6762 ;
ChEMBL	ChEMBL511 ;
CompTox Dashboard (EPA)	DTXSID9023542 ;
ECHA InfoCard	100.001.912
Chemical and physical data
Formula	C17H23N3O
Molar mass	285.391 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C;
	InChI InChI=1S/C17H23N3O/c1-19(2)12-13-20(17-6-4-5-11-18-17)14-15-7-9-16(21-3)10-8-15/h4-11H,12-14H2,1-3H3 ; Key:YECBIJXISLIIDS-UHFFFAOYSA-N ;
	(verify)

Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H₁ receptor as an inverse agonist.^[1] It rapidly permeates the brain often causing drowsiness.

The medication has negligible anticholinergic activity, with 130,000-fold selectivity for the histamine H₁ receptor over the muscarinic acetylcholine receptors (for comparison, diphenhydramine had 20-fold selectivity for the H₁ receptor).^[2]

It was patented in 1943 and came into medical use in 1949.^[3] It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.^[4] It is also the active ingredient of the topical antihistamine creams Anthisan and Neoantergan sold for the treatment of insect bites, stings, and nettle rash.

References

^ Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 Suppl 1 (S1): S127-35. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.
^ Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987). "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology. 43 (3): 277–82. doi:10.1254/jjp.43.277. PMID 2884340.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495.
^ "Active Ingredients for Midol Complete". Archived from the original on 2009-12-02. Retrieved 2009-12-08.

[1] Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 Suppl 1 (S1): S127-35. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.

[pmid2884340-2] Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987). "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology. 43 (3): 277–82. doi:10.1254/jjp.43.277. PMID 2884340.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495.

[4] "Active Ingredients for Midol Complete". Archived from the original on 2009-12-02. Retrieved 2009-12-08.

[1]

[2]

[3]

[4]

Mepyramine

See also

References