Mepyramine

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.

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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.912
Chemical and physical data
FormulaC17H23N3O
Molar mass285.391 g·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,12-14H2,1-3H3 checkY
  • Key:YECBIJXISLIIDS-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

It is used in over-the-counter combination products to treat the common cold and menstrual symptoms such as Midol Complete.[6] It is also the active ingredient of the topical antihistamine creams Anthisan[7] and Neoantergan[1] sold for the treatment of insect bites, stings, and nettle rash.

See also

References
  1. 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. 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, Ganellin CR (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. 6 (9): 408–412. doi:10.1016/S0361-1124(77)80006-3. PMID 330911.
  6. "Active Ingredients for Midol Complete". Bayer HealthCare LLC. Archived from the original on 2009-12-02. Retrieved 2009-12-08.
  7. "Anthisan Cream - Patient Information Leaflet (PIL)". SANOFI Consumer Healthcare.
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