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Mepyramine

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Mepyramine
Clinical data
Other namesPyrilamine;N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Routes of
administration		oral, topical,
ATC code
Legal status
Legal status
Identifiers
  • N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.001.912Edit this at Wikidata
Chemical and physical data
FormulaC17H23N3O
Molar mass285.391g·mol−1
3D model (JSmol)
  • 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,12-14H2,1-3H3checkY
  • Key:YECBIJXISLIIDS-UHFFFAOYSA-NcheckY
☒NcheckY(what is this?)(verify)

Mepyramine,also known aspyrilamine,is afirst generation antihistamine,targeting theH1receptoras aninverse agonist.[1]Mepyramine rapidly permeates the brain, often causingdrowsiness.[2]It is often sold as amaleatesalt,pyrilamine maleate.

The medication has negligibleanticholinergicactivity, with 130,000-foldselectivityfor thehistamineH1receptorover themuscarinic acetylcholine receptors(for comparison,diphenhydraminehad 20-fold selectivity for the H1receptor).[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 USFDAincluded it in the list of chemicals and compounds barred from use inover-the-counternighttime sleep aid products in 1989.[6]

It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such asMidol 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

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References

[edit]
  1. ^abParsons 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.PMC1760721.PMID16402096.
  2. ^ "Mepyramine".drugbank.com.Retrieved8 May2021.
  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.PMID2884340.
  4. ^Fischer J, Gannelin CR, eds. (2006).Analogue-based Drug Discovery.John Wiley & Sons. p. 545.ISBN9783527607495.
  5. ^abThornton 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.PMID330911.
  6. ^54FR6826
  7. ^"Active Ingredients for Midol Complete".Bayer HealthCare LLC.Archived fromthe originalon 2 December 2009.Retrieved8 December2009.
  8. ^"Anthisan Cream - Patient Information Leaflet (PIL)".Medicines.org.
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