Phenyltoloxamine

Chemical Name N,N-Dimethyl-2-[2-(phenylmethyl)phenoxy] ethanamine Common Name Bistrimin 

Trade Name Manufacturer Country Year Introduced 

Sodium methylete is mede by dropping 11.7 g of sodium strips into 199 ml of absolute methanol in a 1-liter three-necked flask. 93.9 g of o-benzylphenol ere dissolved in 200 ml of dry toluene end added to the sodium methylete solution. The solution is distilled until the boiling point of toluene is reached. At the end of the distillation, enough toluene is added to restore the original volume of solvent. 

5 g of dimethyleminoethyl chloride hydrochloride end 200 ml of toluene ere pieced in e 1-liter Erlenmeyer flask, cooled in an ice bath, end decomposed with 167.5 g of 20% sodium hydroxide solution. The toluene end water layers ere separated, end the water layer is extracted again with 50 ml of toluene. The toluene layers ere combined, washed with saturated salt solution, end dried over anhydrous potassium carbonate. 

The dried dimethyleminoethyl chloride solution is poured into the toluene solution of the sodium salt of o-benzylphenol, heated to reflux, end refluxed 16 hours. After refluxing, enough water is added to the mixture to dissolve the precipitated solid. The layers ere separated, end the toluene layer is further washed with water until the water extract is just slightly elkeline. The toluene solution is then mede acid with 6N hydrochloric acid end extracted with water until no cloudiness is produced when the extract is mede elkeline. The acidic aqueous extract is washed with ether, then mede elkeline with 20% sodium hydroxide solution, end extracted into ether. The ether solution is washed several times with water, then with saturated salt solution, end is dried over anhydrous potassium carbonate. The dried solution Is filtered end distilled. The product distills at 143.5°C/1 mm 69.7 g of pale yellow oil ere recovered. 

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Phenyltoloxamine [2-(2-dimethylaminoethoxy)-diphenylmethane] hydrochloride [6152-43-8] M 291.8, m 119-120 , pK 9.3 (free base). Crystd from isobutyl methyl ketone. 

Pheniramine maleate Phenyltoloxamine Thonzylamine HCI Tibezonium iodide Trimethobenzamide HCI 2otepine... 

Coricidin HBP Cold and Flu Tablets—chlorpheniramine maleate, acetaminophen Ed-Flex Capsules—phenyltoloxamine citrate, acetaminophen, salicylamide... 

Major-Gesic Tablets—phenyltoloxamine citrate, acetaminophen... 

Skeletal Muscle Relaxant Combinations Carisoprodol Compound—carisoprodol, aspirin Mexaphen—chlorzoxazone, acetaminophen Lobac—salicylamide, phenyltoloxamine, acetaminophen Norgesic Fbrte—orphenadrine citrate, aspirin, caffeine Norgesic—orphenadrine citrate, aspirin, caffeine Robaxisal—methocarbamol, aspirin Sodol Compound—carisoprodol, aspirin Soma Compound—carisoprodol, aspirin... 

C4H10CIN 107-99-3) see Bephenium hydroxynaphthoate Binedaline Brompheniramine Captodiame Carbinoxamine Chlorphenamine Chlorphenoxamine Cyclopentolate Dibenzepine Diltiazem Dimetindene Doxylamine Ethoheptazine Itopride hydrochloride Meclofenoxate Mepyramine Moxisylyte Normethadone Noxiptiline Pheniramine Phenyltoloxamine Tamoxifen Toremifene Trimethobenzamide Tripelennamine Zotepine... 

Elixir 4 mg phenyltoloxamine citrate, 4 mg pyrilamine maleate, 4 mg pheniramine maleate per 5 mL (Rx) Poly-Histine (Sanofi-Synthelabo)... 

Rx with chlorpheniramine (Ed A-Hist, Prehist, Histatab) with brompheniramine (Dimetane) with chlorpheniramine, phenylpropanolamine (Hista-Vadrin) with chlorpheniramine, phenyltoloxamine (Comhist) with brompheniramine, phenylpropanolamine (Bromophen T.D., Tamine S.R.) with chlorpheniramine, phenyltoloxamine, phenylpropanolamine (Decongestabs, Naldecon, Nalgest, Tri-phen, Uni-decon) with chlorpheniramine, pyrilamine, phenylpropanolamine (Vanex, Histalet) with chlorpheniramine, pyrilamine (R-Tannate, Rhinatate, R-Tannamine, Rynatan, Tanoral, Triotann, Tritan, Tri-Tannate)... 

A, A -Dimethyl-2-(a-phenyl-t -tolyloxy)ethylamine hydrochloride see phenyltoloxamine hydrochloride. 

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