Mepyramine

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. It also has anticholinergic properties. However, its anticholinergic potency is negligible compared to its antihistaminergic activity; it has an H₁ to muscarinic K_i ratio of 130,000 to 1, compared to a ratio of 20 to 1 for diphenhydramine.[2]

Mepyramine

Clinical data
Other names	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^Y 59-33-6 (maleate)
PubChem CID	4992
IUPHAR/BPS	1227
DrugBank	DB06691^N
ChemSpider	4818^Y
UNII	HPE317O9TL
KEGG	D08183^Y
ChEBI	CHEBI:6762^N
ChEMBL	ChEMBL511^Y
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^Y Key:YECBIJXISLIIDS-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

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.

See also

• Chloropyramine (chloro instead of methoxy)

References

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.
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.
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.