Mepyramine

Mepyramine
Names
Other namesPyrilamine; N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
IUPAC name
  • N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
Clinical data
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Routes of
use		oral, topical,
External links
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Legal
Legal status
Chemical and physical data
FormulaC17H23N3O
Molar mass285.391 g·mol−1
3D model (JSmol)
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 checkY
  • Key:YECBIJXISLIIDS-UHFFFAOYSA-N checkY

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]

Medical use

It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete.[4] It is also the active ingredient of the topical antihistamine creams Anthisan[5] and Neoantergan[1] sold for the treatment of insect bites, stings, and nettle rash.

History

It was patented in 1943 and came into medical use in 1949.[6] It was marketed under the names Histadyl, Histalon, Neo-Antergan, Neo-Pyramine, and Nisaval.[7] 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.[7]

Anti-histamine cream

See also

References

  1. 1 2 Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 (Suppl 1): S127–S135. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.
  2. ↑ "Mepyramine". drugbank.com. Archived from the original on 16 May 2021. 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. ↑ "Active Ingredients for Midol Complete". Bayer HealthCare LLC. Archived from the original on 2009-12-02. Retrieved 2009-12-08.
  5. ↑ "Anthisan Cream - Patient Information Leaflet (PIL)". SANOFI Consumer Healthcare. Archived from the original on 2022-09-30. Retrieved 2023-04-02.
  6. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495. Archived from the original on 2023-01-12. Retrieved 2023-04-02.
  7. 1 2 Thornton WE (September 1977). "Sleep aids and sedatives". Jacep. 6 (9): 408–412. doi:10.1016/S0361-1124(77)80006-3. PMID 330911.
Identifiers:
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