Mepyramine

Mepyramine
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a606008
ATC code	R06AC01 (WHO) D04AA02 (WHO);
ECHA InfoCard	100.001.912
Identifiers
	IUPAC name N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine;
Synonyms	N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
CAS Number	91-84-9 ;
PubChem CID	4992;
IUPHAR/BPS	1227;
DrugBank	DB06691 ;
ChemSpider	4818 ;
UNII	HPE317O9TL;
KEGG	D08183 ;
ChEBI	CHEBI:6762 ;
ChEMBL	CHEMBL511 ;
Chemical and physical data
Formula	C17H23N3O
Molar mass	285.38 g/mol
3D model (Jmol)	Interactive image;
	SMILES O(c1ccc(cc1)CN(c2ncccc2)CCN(C)C)C ;
	InChI 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 ; Key:YECBIJXISLIIDS-UHFFFAOYSA-N ;
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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]

^ 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.
^ Active Ingredients for Midol Complete
^ R.J. Horclois, U.S. Patent 2,502,151 (1950).
^ 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.
^ D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).

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[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): 1999–2002. doi:10.1021/ja01214a037. PMID 21001124.

[5] D. Bovet, R. Horclois, F. Walthert, C.R. Soc. Biol., 138, 99 (1944).

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v t e Antipruritics (D04)

Antihistamines for topical use	Thonzylamine Mepyramine Thenalidine Tripelennamine Chloropyramine Promethazine Tolpropamine Dimetindene Clemastine Bamipine Isothipendyl Diphenhydramine Chlorphenoxamine

Anesthetics for topical use	Lidocaine Dibucaine Oxybuprocaine Benzocaine Quinisocaine Tetracaine Pramocaine

Others	Corticosteroids (e.g., hydrocortisone) Counterirritants (e.g., mint oil, menthol, camphor) Nalfurafine

v t e Antihistamines (R06)

Aminoalkyl ethers	Bromazine (bromodiphenhydramine) Carbinoxamine Clemastine Chlorphenoxamine Diphenylpyraline Diphenhydramine Doxylamine Orphenadrine Phenyltoloxamine

Substituted alkylamines	Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Dimetindene Pheniramine Talastine

Substituted ethylenediamines	Chloropyramine Histapyrrodine Mepyramine Methapyrilene Tripelennamine (pyribenzamine)

Phenothiazine derivatives	Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine

Piperazine derivatives	Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Hydroxyzine Meclizine Oxatomide

Others for systemic use	Antazoline Azanator Azatadine Bamipine Cyproheptadine Deptropine Ebastine Emedastine Epinastine Ketotifen Latrepirdine Mebhydrolin Mizolastine Olopatadine Phenindamine Pimethixene Pyrrobutamine Quifenadine Rupatadine Triprolidine selective (Acrivastine Astemizole Azelastine Bilastine Desloratadine Fexofenadine Loratadine Terfenadine)

For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Promethazine Thenalidine

Mepyramine

Synthesis[edit]

See also[edit]

References[edit]

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