Mepyramine

Mepyramine
Clinical data
Other names	N-[2-(dimethylamino)ethyl]-N-[(4-methoxyphenyl)methyl]pyridin-2-amine
AHFS/Drugs.com	International Drug Names
MedlinePlus	a606008
ATC code	R06AC01 (WHO) D04AA02 (WHO);
Identifiers
	IUPAC name N-(4-methoxybenzyl)-N',N'-dimethyl-N-pyridin-2-ylethane-1,2-diamine;
CAS Number	91-84-9 ; 59-33-6 (maleate);
PubChem CID	4992;
IUPHAR/BPS	1227;
DrugBank	DB06691 ;
ChemSpider	4818 ;
UNII	HPE317O9TL;
KEGG	D08183 ;
ChEBI	CHEBI:6762 ;
ChEMBL	ChEMBL511 ;
CompTox Dashboard (EPA)	DTXSID9023542 ;
ECHA InfoCard	100.001.912
Chemical and physical data
Formula	C17H23N3O
Molar mass	285.38 g/mol g·mol−1
3D model (JSmol)	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 ;
	(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

References

^ 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	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Pheniramine Promethazine Thenalidine Thonzylamine Tolpropamine Tripelennamine
Anesthetics for topical use	Benzocaine Cinchocaine Dibucaine Lidocaine Oxybuprocaine Pramocaine Quinisocaine Tetracaine
Others	Corticosteroids (e.g., hydrocortisone) Counterirritants (e.g., mint oil, menthol, camphor) Difelikefalin Doxepin Nalfurafine

v t e Antihistamines (R06)
Benzimidazoles (*)	Astemizole Azelastine Bilastine Emedastine Mizolastine Talastine
Diarylmethanes	Diarylmethoxyalkylamines: Bromazine (bromodiphenhydramine) Carbinoxamine Chlorphenoxamine Clemastine Diphenhydramine (+naproxen) Diphenylpyraline Doxylamine Ebastine Orphenadrine Diphenylmethanolpiperidines: Fexofenadine Terfenadine Diphenylmethylpiperazines: Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Etodroxizine Hydroxyzine Meclizine Oxatomide Phenylpyridinylpropanamines: Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Pheniramine Others: Acrivastine Bamipine Dimetindene Phenyltoloxamine Pyrrobutamine Quifenadine Triprolidine
Ethylenediamines	Antazoline Chloropyramine Histapyrrodine Mepyramine (pyrilamine) Methapyrilene Phenbenzamine Thenalidine Tripelennamine (pyribenzamine)
Tricyclics	Dibenzocycloheptenes: Antidepressants (e.g., amitriptyline) Azatadine Cyproheptadine Deptropine Desloratadine Ketotifen Loratadine Rupatadine Phenothiazines: Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine Others: Antidepressants (e.g., doxepin, mirtazapine, trimipramine) Epinastine Latrepirdine Mebhydrolin Olopatadine Perlapine Phenindamine Pimethixene
Others	Phenylpiperazines: Antidepressants (e.g., trazodone) Phenbenzamine
For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Doxepin Isothipendyl Mepyramine (pyrilamine) Promethazine

Synthesis

See also

References