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Mepyramine

Clinical data
Other names	Pyrilamine; N--N-pyridin-2-amine
AHFS/Drugs.com	International Drug Names
MedlinePlus	a606008
Routes of administration	By mouth, topical
Drug class	First-generation antihistamine
ATC code	R06AC01 (WHO) D04AA02 (WHO)
Legal status
Legal status	In general: Over-the-counter (OTC)
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
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
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Mepyramine, also known as pyrilamine, is a first-generation antihistamine, targeting the H₁ receptor as an inverse agonist. Mepyramine rapidly permeates the brain, often causing drowsiness. It is often sold as a maleate salt, pyrilamine maleate.

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).

It was patented in 1943 and came into medical use in 1949. It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval. In the 1960s and 70s it was a very common component in over-the-counter sleep aids such as Alva-Tranquil, Dormin, Sedacaps, Sominex, Nytol, and many others. The US Food and Drug Administration (FDA) included it in the list of chemicals and compounds barred from use in over-the-counter (OTC) nighttime sleep aid products in 1989.

It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete. 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

References

1. ^ Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 (Suppl 1) (published 2 February 2009): S127 – S135. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.
2. "Mepyramine". drugbank.com. Retrieved 8 May 2021.
3. 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): 277–282. doi:10.1254/jjp.43.277. PMID 2884340.
4. Fischer J, Gannelin CR, eds. (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495.
5. ^ Thornton WE (September 1977). "Sleep aids and sedatives". Journal of the American College of Emergency Physicians (JACEP). 6 (9): 408–412. doi:10.1016/S0361-1124(77)80006-3. PMID 330911.
6. 54 FR 6826
7. "Active Ingredients for Midol Complete". Bayer HealthCare LLC. Archived from the original on 2 December 2009. Retrieved 8 December 2009.
8. "Anthisan Cream - Patient Information Leaflet (PIL)". Medicines.org.

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