Mepyramine

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Mepyramine
Mepyramine.svg
Systematic (IUPAC) name
N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Legal status
?
Identifiers
CAS number91-84-9 YesY
59-33-6 (maleate)
ATC codeR06AC01 D04AA02
PubChemCID 4992
IUPHAR ligand1220
DrugBankDB06691
ChemSpider4818 YesY
UNIIHPE317O9TL YesY
KEGGD08183 YesY
ChEBICHEBI:6762 N
ChEMBLCHEMBL511 YesY
SynonymsN-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
Chemical data
FormulaC17H23N3O 
Mol. mass285.38 g/mol
 N (what is this?)  (verify)
 
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Mepyramine
Mepyramine.svg
Systematic (IUPAC) name
N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine
Clinical data
AHFS/Drugs.comInternational Drug Names
MedlinePlusa606008
Legal status
?
Identifiers
CAS number91-84-9 YesY
59-33-6 (maleate)
ATC codeR06AC01 D04AA02
PubChemCID 4992
IUPHAR ligand1220
DrugBankDB06691
ChemSpider4818 YesY
UNIIHPE317O9TL YesY
KEGGD08183 YesY
ChEBICHEBI:6762 N
ChEMBLCHEMBL511 YesY
SynonymsN-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
Chemical data
FormulaC17H23N3O 
Mol. mass285.38 g/mol
 N (what is this?)  (verify)

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[edit]

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

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 1760721. PMID 16402096. 
  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. doi:10.1021/ja01214a037. PMID 21001124.  edit
  5. ^ D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).