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Mepyramine

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Title: Mepyramine  
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Subject: Triprolidine, Meclizine, Phenyltoloxamine, Pheniramine, Pizotifen
Collection: Amines, Aromatic Amines, H1 Receptor Antagonists, Phenol Ethers, Pyridines
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Mepyramine

Mepyramine
Systematic (IUPAC) name
N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
Clinical data
AHFS/Drugs.com
MedlinePlus
Legal status
?
Identifiers
CAS number  YesY
59-33-6 (maleate)
ATC code R06 D04
PubChem
IUPHAR ligand
DrugBank
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  N
ChEMBL  YesY
Synonyms N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
Chemical data
Formula C17H23N3O 
Mol. mass 285.38 g/mol
 N   

Mepyramine, also known as pyrilamine, is a first generation antihistamine, targeting the H1 receptor.[1] However, it rapidly permeates the brain often causing drowsiness. It also has anticholinergic properties. It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.[2] 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

Pyrilamine synthesis:[3][4][5]

See also

References

  1. ^ Parsons, Mike E.; Ganellin, C. Robin (January 2006). "Histamine and its receptors". British Journal of Pharmacology 147 (S1): S127–S135.  
  2. ^ Active Ingredients for Midol Complete
  3. ^ R.J. Horclois, U.S. Patent 2,502,151 (1950).
  4. ^ 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.  
  5. ^ D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).


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