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	285.391 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 as an inverse agonist.^[1] It rapidly permeates the brain often causing drowsiness. It also has anticholinergic properties. However, its anticholinergic potency is negligible compared to its antihistaminergic activity; it has an H₁ to muscarinic K_i ratio of 130,000 to 1, compared to a ratio of 20 to 1 for diphenhydramine.^[2]

It was patented in 1943 and came into medical use in 1949.^[3] It is used in over-the-counter combination products to treat the common cold and menstrual symptoms.^[4] 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.

References

^ Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 Suppl 1 (S1): S127-35. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.
^ Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987). "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology. 43 (3): 277–82. doi:10.1254/jjp.43.277. PMID 2884340.
^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
^ "Active Ingredients for Midol Complete". Archived from the original on 2009-12-02. Retrieved 2009-12-08.

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[1] Parsons ME, Ganellin CR (January 2006). "Histamine and its receptors". British Journal of Pharmacology. 147 Suppl 1 (S1): S127-35. doi:10.1038/sj.bjp.0706440. PMC 1760721. PMID 16402096.

[2] Kubo N, Shirakawa O, Kuno T, Tanaka C (March 1987). "Antimuscarinic effects of antihistamines: quantitative evaluation by receptor-binding assay". Japanese Journal of Pharmacology. 43 (3): 277–82. doi:10.1254/jjp.43.277. PMID 2884340.

[Fis2006-3] Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 545. ISBN 9783527607495. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)

[4] "Active Ingredients for Midol Complete". Archived from the original on 2009-12-02. Retrieved 2009-12-08.

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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) Difelikefalin 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

See also

References