Mepyramine
- R06AC01 (WHO) D04AA02 (WHO)
- In general: Over-the-counter (OTC)
- N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
- 91-84-9 Y
59-33-6 (maleate)
- 4992
- 1227
- DB06691 N
- 4818 Y
- HPE317O9TL
- D08183 Y
- CHEBI:6762 N
- ChEMBL511 Y
- DTXSID9023542
- Interactive image
- O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C
- 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
Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor as an inverse agonist.[1] Mepyramine rapidly permeates the brain, often causing drowsiness.[2] 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).[3]
It was patented in 1943 and came into medical use in 1949.[4] It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval.[5] 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.[5] The US FDA included it in the list of chemicals and compounds barred from use in over-the-counter nighttime sleep aid products in 1989.[6]
It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete.[7] It is also the active ingredient of the topical antihistamine creams Anthisan[8] and Neoantergan[1] sold for the treatment of insect bites, stings, and nettle rash.
See also
- Chloropyramine (chloro instead of methoxy)
References
- ^ a b 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.
- ^ "Mepyramine". drugbank.com. Retrieved 8 May 2021.
- ^ 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.
- ^ Fischer J, Gannelin CR, eds. (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495.
- ^ a b 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.
- ^ 54 FR 6826
- ^ "Active Ingredients for Midol Complete". Bayer HealthCare LLC. Archived from the original on 2 December 2009. Retrieved 8 December 2009.
- ^ "Anthisan Cream - Patient Information Leaflet (PIL)". Medicines.org.
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