At the dose level of 2 microgramscm2, benzocaine was rapidly absorbed and extensively metabolized 80% by acetyltransferase. The effect of temperature on phase separation induced by these drugs was not reported previously. Benzocaine can be prepared by esterification using 4 aminobenzoic acid and ethanol. You are purchasing 100 grams of 99% minimum purity benzocaine hydrochloride. Nh2 is also protonated 2 nucleophillic attack of the alcohol at the carbonyl carbon 3 loss of oxonium leaving group 4 proton transfer leading to a. Procaine, isocaine, procainamide, tocainide, and mexiletine are other members of this family of compounds. Show the complete reaction mechanism for the synthesis of benzocaine from paba, sulfuric acid and ethanol. Benzocaine is structurally related to parabens it differs from ethylparaben in a nh 2 instead of the oh group attached to the benzene ring, and there are no data available on the solubility in dioxanewater at several temperatures. Benzocaine is the most popular cutting agent worldwide, benzocaine was used in synthesis of leteprinim. Benzocaine is an ester and can be prepared via acidcatalyzed. The effect of dose and enzymatic inhibition on the percutaneous absorption and metabolism of benzocaine was studied in vitro in the hairless guinea pig. Apply basic techniques of organic synthesis to the preparation of drugs. The synthesis of lidocaine introduction lidocaine trade names lidothesin, xylocain, anestacon is an important member of class 1b drugs used as local anesthetics. Benzocaine is the ethyl ester of 4aminobenzoic acid 2.
Benzocaine is a benzoate ester having 4aminobenzoic acid as the acid component and ethanol as the alcohol component. Which brand of paper towel is the strongest experiment. Resume preparation tax deductible research proposals. Combine the aqueous extracts in a 125ml erlenmeyer flask or a large beaker, depending on the volume of extractions, cool the flask or beaker in an icesalt bath, and neutralize the acidic solution by addition of 3. Synthesis of phenacetin from acetaminophen labeled. Why is the melting point of benzocaine significantly lower than aminobenzoic acid. Resume preparation tax deductible research proposals re application letter.
Benzocaine containing topical formulations should not be used in children younger than 2 years of age unless prescribed by a physician. Students undertake, in a severalweek independent project, the multistep synthesis of a. The onset of action is rapid benzocaine is most commonly available as a 20% aerosol spray that is easily applied to the oropharyngeal mucosa. Will ptoluidine dissolve when it is mixed with an aqueous solution of hcl. Elimination of benzocaine from plasma is characterized by a very rapid initial phase followed by a relatively slow terminal phase. A ester of paba and ethanol synthesis of benzocaine. The purpose of this experiment was to synthesize benzocaine, a common topical anesthetic, via acidcatalyzed fisher esterfication of paminobenzoic acid and ethanol results and discussion. Webmd provides common contraindications for benzocaine benzyl benzoate topical. Add carbopol in portions to the alcohol benzocaine mixture with continual stirring.
An experiment was performed to synthesize ethyl 4aminobenzoate benzocaine, an ester, from absolute ethanol an alcohol and 4aminobenzoic acid a carboxylic acid and sulfuric acid as a catalyst. Abstract the multistep synthesis of benzocaine was carried out starting with ptoluidine in a four step reaction. In step 1 common reduction of aromatic paranitrobenzoic acid by tin and hydrochloric acid to paraaminobenzoic acid and in step 2 esterification of paraaminobenzoic acid by sulphuric acid and ethanol to benzocaine occurring called fischer esterification. Synthesis of benzocainelocal anaesthetic with the yield. Relevant identified uses of the substance or mixture and uses advised against not applicable. Preparing benzocaine is often done in a school lab setting to demonstrate the acidcatalyzed esterification of a carboxylic. Compare benzocaine vs prilocaine comprehensive analysis.
Contraindications for benzocainebenzyl benzoate topical. Benzocaine, in contrast, is active as a local anesthetic but is not used for injection. A threestep synthesis is used to create benzocaine. Cetacaine topical anesthetic gel should be applied directly to the site where pain control is required. Carbomer is the generic name for carbopol family of resins. Introduction esters are important compounds in organic chemistry. Synthesis of benzocaine lab help in this lab we used 4aminobenzoic acid, sulfuric acid, ethanol100%, and sodium bicarbonate. The synthesis of lidocaine university of san diego. Anesthesia is produced in approximately 30 seconds with an approximate duration of thirty to sixty minutes. Uses, side effects, interactions, pictures, warnings density calculation. Benzocaine can be prepared by esterification using 4. To produce an ester, one can utilize an esterification reaction.
Buyer assumes all liability for the use of this item. Synthesis of aspirin post lab questions media and pop culture essays examples. Find out what health conditions may be a health risk when taken with benzocaine benzyl benzoate topical. For the synthesis of benzocaine etpaba, paminobenzoic acid paba in 99% purity is usually used by applying the socalled fischer esterification reaction. Synthesising benzocaine via reflux with a condenser uk essays. The preparation of the local anesthetic, benzocaine, by an. And if that is the case would i just convert to moles of ptoluidine, multiply by 1. I am starting with ptoluidine pmethylacetanalide pacetamidobenzoic acid paminobenzoic acid benzocaine i am starting with 1. What do you put in the round bottom flask prior to starting the reaction. The reaction mechanism for the synthesis of benzocaine is divided into six key steps. A surface anaesthetic, it is used to suppress the gag reflex, and as a lubricant and topical anaesthetic on the larynx, mouth, nasal cavity, respiratory tract, oesophagus, rectum, urinary tract, and vagina. The sulfuric acid in the benzocaines synthesis is used as. Comparative efficacy of 2 topical anesthetics for the.
Take your hr comms to the next level with prezi video. Synthesis of ethyl paminobenzoate benzocaine from p. Find patient medical information for lidocaine hcl benzocaine methyl salicylatecapsaicin topical on webmd including its uses, side effects and. In this video, i am synthesizing benzocaine, and explaining how the process was planned. Organic ii lab report 8 synthesis of benzocaine chem. Synthesis of benzocaine from pnitrotoluene or even toluene is a very good multistep synthesis to get familiar with organic chemistry technics, i often recommend it to begginers, lots of trivial reactions, which helps one discover workup technics etc. Treatment of benzocaine with hydrazine leads to aminostimil a compound related to isoniazid.
What type of filtration will you use to collect the product. The preparation of the local anesthetic, benzocaine, by an esterification reaction. Each 200 mg dose of cetacaine topical anesthetic gel contains 28 mg of benzocaine, 4 mg of butamben and 4 mg of tetracaine hcl. Significant differences in favor of the benzocaine group were also recorded for prid at 10, 15, and 30. Metabolism of benzocaine during percutaneous absorption in. The purpose of this lab is to synthesize benzocaine, an ester, from p aminobenzoic acid, acarboxylic acid, by fischer esterification. Important key differences between benzocaine and lidocaine. The salt ions will dissolve in water because of iondipole imfs. Benzocaine definition of benzocaine by medical dictionary.
Buyer agrees to not hold rnd center or amazon liable for the use of this item. Benzocaine is an ester and can be prepared via acidcatalyzed fisher. Synthesis of benzocaine quiz synthesis of benzocaine. The ethanol used was denatured, and contained about 90% ethanol by weight. Metabolism, elimination, and pharmacokinetics of the fish.
It is used primarily in skin preparations, in which it can be included in an ointment of salve for direct. Norpatchoulenol is a tricyclic terpenoid found in commercial patchouli extract in small quantities, and thought to contribute significantly to the aroma of. Put alcohol in beaker, and add benzocaine with stirring. All of them have an amine functional group in common, which appears to be. When the solution turns completely clear inject 4 ml of 70% sodium ethoxide in ethanol. Sciencemadness discussion board synthesis of benzocaine. Benzocaine is a local anesthetic commonly used for pain relief. For the synthesis of benzocaine etpaba, paminobenzoic acid paba in 99% purity is usually used by applying the socalled fischer. You are purchasing 25 grams of 99% minimum purity benzocaine hydrochloride. The reactions were acetylation, oxidation, hydrolysis and fischer esterification. What is the purpose of adding sodium bicarbonate to raise the ph. During the initial elimination phase, the majority of benzocaine is lost from the fish while only a small portion of the benzocaine is lost during the terminal elimination phase.
Benzocaine is a waterinsoluble estertype local anesthetic agent that is mainly useful for topical application. Preparation and purification of the topical local anaesthetic benzocaine, ethyl4aminobenzoate, via two alternative routes. Yes, it will because of the formation of ammonium salts. Single step synthesis of benzocaine christopher nusbaum dates performed. To prepare benzocaine a local anesthetic from paminobenzoic acid and ethanol, via a fischer esterification reaction. If in scope, these drugs will include rxnorm normal forms when editing is complete. The classic, optimal way of benzocaine synthesis is the reduction of the nitro group of the ethyl ester of 4nitrobenzoic acid to benzocaine by hydrogen, which generates directly in the reaction medium by the reaction of iron filings with dilute acids 2426. This study compared the effectiveness of topical benzocaine 20% versus a combination of lidocaine, tetracaine, and phenylephrine in providing sufficient analgesia for the placement of orthodontic temporary anchorage devices tads. How to prepare benzocaine fischer esterification with. Identification ghs product identifier other means of identification. Evonik benzocaine innovation power challenge ekipa. Synthesis and characterisation of benzocaine experiment practical report aim. Ejectdelay benzocaine dosing, indications, interactions.
The product of each reaction was carried over to the next to complete the synthesis of benzocaine. The drug is an ingredient in aaa spray, intralgin, merocaine and tyrozets. Benzocaine was prepared in this experiment by the direct esteri. It is powdery material with some small clumping from time to time. Benzocaine benzocaine should be used with caution in infants and young children because increased absorption through the skin with excessive use may result in methemoglobinemia. They are used in numerous types ofsynthetic reactions, to create different products for a vast array of purposes, including medicinaland cosmetic. Benzocaine hydrochloride hcl, high purity, 100 grams. The experiment was to synthesise benzocaine via reflux with a. The preparation of the local anesthetic, benzocaine penn state. Often used in lozenges in combination with antiseptics. Benzocaine can be prepared by esterification using 4aminobenzoic acid and ethanol. It does not suffuse well into tissue and is not watersoluble. First paminobenzoic acid is produced from taking pacetotoluidide and oxidizing it with magnesium sulfate. The absolute ethanol, sulfuric acid and 4aminobenzoic acid are refluxed.
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