Chemistry:Mepyramine

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Short description: First generation antihistamine
Mepyramine
Mepyramine.svg
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
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC17H23N3O
Molar mass285.391 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

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]

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. 1.0 1.1 "Histamine and its receptors". British Journal of Pharmacology 147 (Suppl 1): S127–S135. January 2006. doi:10.1038/sj.bjp.0706440. PMID 16402096. 
  2. "Mepyramine". https://go.drugbank.com/drugs/DB06691. 
  3. "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology 43 (3): 277–282. March 1987. doi:10.1254/jjp.43.277. PMID 2884340. 
  4. (in en) Analogue-based Drug Discovery. John Wiley & Sons. 2006. p. 545. ISBN 9783527607495. https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA545. 
  5. 5.0 5.1 "Sleep aids and sedatives". Journal of the American College of Emergency Physicians 6 (9): 408–412. September 1977. doi:10.1016/S0361-1124(77)80006-3. PMID 330911. 
  6. "Active Ingredients for Midol Complete". Bayer HealthCare LLC. http://midol.com/menstrual_complete_caps.html#q1. 
  7. "Anthisan Cream - Patient Information Leaflet (PIL)". SANOFI Consumer Healthcare. https://www.medicines.org.uk/emc/product/1618/pil.