Methaphenilene

Methaphenilene
Identifiers
	IUPAC name N,N-Dimethyl-N′-phenyl-N′-(thiophen-2-ylmethyl)ethane-1,2-diamine;
CAS Number	493-78-7 ;
ChemSpider	9884 ;
UNII	Q1MP2MRW1E;
CompTox Dashboard (EPA)	DTXSID5020817 ;
ECHA InfoCard	100.007.074
Chemical and physical data
Formula	C15H20N2S
Molar mass	260.40 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCN(Cc1cccs1)c2ccccc2;
	InChI InChI=InChI=1S/C15H20N2S/c1-16(2)10-11-17(13-15-9-6-12-18-15)14-7-4-3-5-8-14/h3-9,12H,10-11,13H2,1-2H3 ; Key:LDYJXVUOVPVZKA-UHFFFAOYSA-N ;

Methaphenilene is an antihistamine and anticholinergic.

Synthesis

Methaphenilene can be synthesized from N,N-dimethyl-N′-phenylethane-1,2-diamine by alkylation with 2-(chloromethyl)thiophene.^[1]

References

^ Leonard F, Solmssen UV (June 1948). "Thenyl Substituted Diamines with Antihistaminic Activity". Journal of the American Chemical Society. 70 (6): 2064–7. doi:10.1021/ja01186a023. PMID 18863797.

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[1] Leonard F, Solmssen UV (June 1948). "Thenyl Substituted Diamines with Antihistaminic Activity". Journal of the American Chemical Society. 70 (6): 2064–7. doi:10.1021/ja01186a023. PMID 18863797.

[1]

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