Mepyramine

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Mepyramine
Mepyramine.svg
Clinical data
Other namesPyrilamine; N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
ATC code
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 Edit this at Wikidata
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)

Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor as an inverse agonist.[1] It rapidly permeates the brain often causing drowsiness.[2]

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 is used in over-the-counter combination products to treat the common cold and menstrual symptoms.[5] It is also the active ingredient of the topical antihistamine creams Anthisan[6] and Neoantergan [7]sold for the treatment of insect bites, stings, and nettle rash.

See also[edit]

References[edit]

  1. ^ Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 Suppl 1 (S1): S127-35. 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): 277–82. 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. ^ "Active Ingredients for Midol Complete". Archived from the original on 2009-12-02. Retrieved 2009-12-08.
  6. ^ https://www.medicines.org.uk/emc/product/1618/pil
  7. ^ http://europepmc.org/article/PMC/1760721