Mepyramine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Mepyramine
Mepyramine.svg
Clinical data
Synonyms N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
AHFS/Drugs.com International Drug Names
MedlinePlus a606008
ATC code
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.001.912 Edit this at Wikidata
Chemical and physical data
Formula C17H23N3O
Molar mass 285.38 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor.[1] It rapidly permeates the brain often causing drowsiness. It also has anticholinergic properties. However, its anticholinergic potency is negligible compared to its antihistaminergic activity; it has an H1 to muscarinic Ki ratio of 130,000 to 1, compared to a ratio of 20 to 1 for diphenhydramine.[2] It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.[3] It is also the active ingredient of the topical antihistamine creams Anthisan and Neoantergan, sold for the treatment of insect bites, stings, and nettle rash.

Synthesis[edit]

Pyrilamine synthesis:[4][5][6]

See also[edit]

References[edit]

  1. ^ Parsons, Mike E.; Ganellin, C. Robin (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 (S1): S127–S135. doi:10.1038/sj.bjp.0706440. PMC 1760721Freely accessible. PMID 16402096. 
  2. ^ 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. ISSN 0021-5198. PMID 2884340. 
  3. ^ Active Ingredients for Midol Complete
  4. ^ R.J. Horclois, U.S. Patent 2,502,151 (1950), to Rhône-Poulenc.
  5. ^ Huttrer, C. P.; Djerassi, C.; Beears, W. L.; Mayer, R. L.; Scholz, C. R. (1946). "Heterocyclic amines with antithistaminic activity". Journal of the American Chemical Society. 68 (10): 1999–2002. doi:10.1021/ja01214a037. PMID 21001124. 
  6. ^ D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).