Pyrilamine

Chemical Abstracts Registry No, 101-26-8 Trade Name Manufacturer 

3-Hydroxypyridine Dimethyl carbamic acid chloride Methyl bromide 

Patent 2,572,579 October 23, 1951 assigned t3 Hoffmann-La Roche Inc. 

Chemical Name N-[(4-Methoxyphenyl)methylJ -N, N -dimethyl-N-2-pyridiny -1,2-ethanedi-amine (often used as the maleate) 

Trade Name Manufacturer Country Year Introduced 

43 g of a-p-methoxybenzylaminopyridine (from 4-methoxybenzaldehyde reaction with 2-aminopyridinel are heated in 60 cc of toluene to 95°C to 100°C. 18 g of sodamide (85%) and 110 cc of a 40% toluene solution of 1-dimethylamino-2-chloroethane are added in small amounts alternately with shaking the addition takes 1 hour. Toluene Is distilled off, first at normal pressure, then under reduced pressure, until there remains a pasty mass. The mass is taken up with dilute hydrochloric acid and ether, neutralized to pH 7, and p-methoxybenzyl-aminopyridine separates. After making alkaline using excess of potash, it is extracted with benzene, dried and distilled. The product thereby obtained, N, N -dimethylaminoethyl-N-p-methoxybenzyl-tt-aminopyridine boils at IBb C to 190°C/2 mm. The monohydrochloride melts at 135°C (block Maquenne). 

Common Name Mepyramine, pyranisamine Structural Formula  

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Substitution of a 2-pyridyl residue for the phenyl attached rectly to nitrogen affords a series of potent antihistamines, eparation of these compounds, too, is accomplished by a series alkylation reactions. It is further probable that the order the reaction can be readily interchanged. Thus, alkylation 2-aminopyridine with the chloroethyldimethylamine side chain ads to the diamine, 59. Alkylation with benzyl chloride af-rds tripelenamine (60) reaction with p-methoxybenzyl chloride ads to pyrilamine (61), °... 

Amino-1,3-propanediol lopamidol 2-Aminopyrazine Sulfalene 2-Aminopyridine Diphenpyramide Methapyrilene HCI Phenyramidol Pyrilamine Sulfadiazine Tripelennamine Zolimidine... 

Triacort - Triamcinolone acetonide Triaderm Triamcinolone acetonide Triadol Benorylate Triafed Triprolidine Triagen Chlorotrianisene Triaget - Triamcinolone acetonide Trialona Triamcinolone Trielona Triamcinolone acetonide Triamalone Triamcinolone acetonide Triamcin Triamcinolone diacetete Triamcort Triamcinolone Triemetine Triethylenemelemine Triam Forte Triamcinolone diacetete Trieminic Pyrilamine... 

Tricodeine Cough Cold Liquid—codeine phosphate, pyrilamine maleate... 

Uv absorption, 254 nm 1 = maleic acid 2 = phenylephrine 3 = norephedrine 4 = naphazoline 5 = phenacetin 6 = pyrilamine... 

Systemic administration of the Hi receptor antagonists pyrilamine and diphenhydramine decreased wakefulness and increased NREM sleep in rats (Monti et al., 1986) conversely, intracerebroventricular application of the... 

Hi-receptor agonist 2-thiazolylethylamine dose-dependently increased wakefulness and decreased both NREM sleep and REM sleep. Furthermore, the Hi receptor antagonist pyrilamine blocked the wakefulness-inducing effects of the Hi-receptor agonist 2-thiazolylethylamine (Monti et al., 1986). 

Organic cation/camitine OCTN1 TEA, pyrilamine, quinidine and verapamil... 

Antagonists Pyrilamine (mepyramine) Ranitidine Zolantidine Thioperamide 5 Clobenpropit 5 Ciproxyfan Thioperamide 5 Iodophenpropit 5 J J7777120... 

Brompheniramine maleate Chlorpheniramine maleate Dexchlorpheniramine maleate Ethanolamine class, nonselective Carbinoxamine maleate Clemastine fumarate Diphenhydramine hydrochloride Ethylenediamine class, nonselective Pyrilamine maleate Tripelennamine hydrochloride Phenothiazine class, nonselective Promethazine hydrochloride Piperidine class, nonselective Cyproheptadine hydrochloride Phenindamine tartrate... 

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