Ethyl-p-aminobenzoate hydrochloride

Diethylamino) ethyl-p-aminobenzoate hydrochloride Benzoic acid, 4-amino-, 2-(diethylamino) ethyl ester, monohydrochloride Ethocaine hydrochloride Allocaine S3mcaine B.P. U.S.P, Eur. P. Int. R, Ind. P,... 

Synonyms cas 31-05-8 anesthesol procaine hydrochloride ethyl-p-aminobenzoate hydrochloride... 

Ethyl-p-aminobenzoate hydrochloride. See Procaine hydrochloride Ethyl p-aminobenzoate, 2 mole propoxylate. 

Benzoic acid, p-amino-, 2-(diethylamino) ethyl ester, monohydrochloride Diethylaminoethanol-4-aminobenzoate hydrochloride 2-(Diethylamino) ethyl 4-aminobenzoate hydrochloride 2-Diethylaminoethyl-p-aminobnzoate hydrochloride Ethyl-p-aminobenzoate hydrochloride Empirical C13H20N2O2 CIH Properties Wh. cryst. powd., odorless, tasteless sol. in dil. acids less sol. in chloroform, ether, alcohol very si. sol. in water m.w. 272.81 m.p. 88-92 C... 

Ethyl p-aminobenzoate. Saturate 80 ml (63.2 g, 1.37 mol) of absolute ethanol with dry hydrogen chloride, add 12 g (0.088 mol) of p-aminobenzoic acid and heat the mixture under reflux for 2 hours. Upon cooling, the reaction mixture sets to a solid mass of the hydrochloride of ethyl p-aminobenzoate. It is better, however, to pour the hot solution into excess of water (no hydrochloride separates) and add sodium carbonate to the clear solution until it is neutral to litmus. Filter off the precipitated ester at the pump and dry in the air. The yield of ethyl p-aminobenzoate, m.p. 91 °C, is 10 g (69%). Recrystallisation from rectified spirit does not affect the m.p. 

It should be mentioned that several more drastic simplifications of cocaine appeared on the scene even earlier. The only survivor is ethyl p-aminobenzoate (benzocaine, Table 13-6, No. 5). The others of interest were methyl p-amino-m-hydroxybenzoate (ortho-form), which, like benzocaine, was nontoxic, highly insoluble, and therefore not suitable for parenteral administration. Orthoform has no activity on intact skin, but it was useful as a powder on painful wounds. It was superseded commercially by the position isomer p-hydroxy-m-aminobenzoate methyl ester for reasons of cost since large-scale production of orthoform (as the pure, correct isomer) presented difficulties at the time. It should be pointed out that water-soluble hydrochlorides of the aminobenzoates can be prepared however, their solutions are much too acidic to inject. 

Aminobenzoic acid 2-(diethylamino) ethyl ester p-Aminobenzoic acid diethylaminoethyl ester p-Aminobenzoic acid-2-diethylaminoethyl ester. See Procaine 4-Aminobenzoic acid 2-(diethylamino) ethyl ester hydrochloride p-Aminobenzoic acid-2-diethylaminoethyl ester, hydrochloride. See Procaine hydrochloride 4-Aminobenzoic acid ethyl ester. See Ethyl-p-aminobenzoate... 

Diethylamino) ethyl 4-aminobenzoate hydrochloride 2-Diethylaminoethyl-p-amlnobnzoate hydrochloride. See Procaine hydrochloride Diethylaminoethyl cellulose CAS 9013-34-7... 

Cysteine hydrochloride, nicotinic acid, pantothenic acid plus glycine, pteroylglutamic acid plus p-aminobenzoic acid, and methionine were added in final concentrations of 50, 5, 0.5, and 0.06 iig, per milliliter with and without vitamin Bu, 5 Hfig. per milliliter. Nicotinic acid, 50 Mg. per milliliter, was completely inhibitory, while 6 Mg. per milliliter was not. Pteroylglutamic acid, p-aminobenzoic acid, pyridoxine hydrochloride, glycine, pantothenic acid, and uracil in concentrations of 0.5 Mg. per milliliter without vitamin Bis, and 50, 5, 0.5, and 0.05 Mg. per milliliter with vitamin Bis, 6 nng. per milliliter, were also tested. Ethyl alcohol (12.5%, 2.5%, 0.25%, 0.026%, and 0.0025%) and ammonium hydroxide (5%, 0.5%, 0.05%, and 0.005%) with and without vitamin Bis, 5 MMg- per milliliter, were tested because of their use in dissolving some of the substances listed above. Ethyl alcohol, 12.5% but not 2.6%, and 5% ammonium hydroxide, but not 0.5%, were inhibitory. Leuconostoc citrovorum factor (folinic acid), 75 Mg. per milliliter, did not replace vitamin Bis. 

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