View lab report report sheet for benzocaine synthesis from bio sci 100lw at university of california, irvine. Anesthetics topicalmucosal americaine hemorrhoidal. It is the active ingredient in many overthecounter anesthetic ointments such as products for oral ulcers. Home natural sciences chemisty esterification of benzocaine. Benzocaine, sold under the brand name orajel amongst others, is an ester local anesthetic commonly used as a topical pain reliever or in cough drops. Benzocaine is a short acting local anaesthetic used in a wide variety of clinical situations including mucous membrane anaesthesia, gag reflex suppression, anorectal. As a counter electrode, large surface platinum plate was used. A ester of paba and ethanolsynthesis of benzocaine.
Important key differences between benzocaine and lidocaine. Synthesis of ethyl paminobenzoate benzocaine from p. Report synthesis of benzocaine please fill this form, we will try to respond as soon as possible. Single step synthesis of benzocaine christopher nusbaum dates performed. Pdf procaine and benzocaine are used as local anaesthetic agents used in so called small surgery. Benzocaine is a waterinsoluble estertype local anesthetic agent that is mainly useful for topical application. Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Description download synthesis of benzocaine comments. Introduction esters are important compounds in organic chemistry.
Synthesis of ethyl paminobenzoate benzocaine from p nitrobenzoic acid. Click, drag, and drop to reorder files or press delete to remove any content you dont want. The preparation of the local anesthetic, benzocaine penn state. It is also combined with antipyrine to form ab otic drops to relieve ear pain and remove earwax. The experiment was to synthesise benzocaine via reflux with a condenser and was characterised by examining at the infrared spectrum and chemical shifts of nmr. Pdf benzocaine degradation in oral disintegrating tablet. Report sheet for benzocaine synthesis report sheet for. Files are available under licenses specified on their description page. The onset of action is rapid files dmf, cepcos, japanese dmfs, written confirmation wc details listed on. Experiment nine synthesis and purification of benzocaine.
To practice the techniques of refluxing and vacuum filtration to perform an esterification reaction to create benzocaine from paminobenzoic acid. Oxidation of benzocaine sce as a reference electrode. The ethanol used was denatured, and contained about 90% ethanol by weight. Benzocaine 8ispreparedfrompmethylacetanilide3part c in scheme 1 in a threestep reaction sequence, involving procedures described in this journal14 and in several laboratory instruction manuals overall yields of about 12 to 22 %. Acidcatalyzed ester formation synthesis of benzocaine. Naturally occuring local anesthetics have been used for over a century to dull or alleviate the pain involved with medical procedures. Multistep synthesis in a projectoriented laboratory course.
Benzocaine is a local anesthetic commonly used for pain relief. Refer to the structure of procaine in the table in the above introduction, local anesthetics. Files available from the acs website may be downloaded for personal use only. Preparing benzocaine is often done in a school lab setting to demonstrate the acidcatalyzed esterification of. In this experiment, the synthesis of benzocaine 2 is carried out by the acidcatalyzed esterification of 4aminobenzoic 1 acid with ethanol.
Acetylation of ptoluidine to pmethylacetanilide 7 acetylation is carried out using acetic anhydride in a nucleophilic addition reaction to add an acetyl group c2h3o on to the amine group nh2. Synthesis and characterization of covalently bound benzocaine graphite oxide derivative. Pdf microwaveassisted synthesis of local anaesthetic. Students undertake, in a severalweek independent project, the multistep synthesis of a. Risk of serious and potentially fatal blood disorder. Synthesis of benzocaine h2n co2h etoh h2so4 h2n co2et procedure. The oxidation products of benzocaine the oxidation of benzocaine has been carried out with aps at were dissolved at a concentration of 2. List of drug master files dmf of benzocaine active pharmaceutical ingredient api submitted to the u. Handle all chemicals with care avoid inhaling vapors or contact with skin. Use three 1ml portions of cold water to wash the product crystals from the flask onto the funnel. According to escobel, 2011, aspirin is synthesized through the. Side effects of americaine benzocaine, warnings, uses.
The preparation of the local anesthetic, benzocaine, by an. The synthesis of benzocaine, a common anesthetic prelab. Dried thoroughly by leaving it in an open container until the next lab, weigh it, calculate the % yield, and determine its melting point. All structured data from the file and property namespaces is available under the creative commons cc0 license. Divergent synthesis of prilocaine hydrochloride 5 and benzocaine 8. Find information on anesthetics topicalmucosal americaine hemorrhoidal, anbesol in daviss drug guide including dosage, side effects, interactions, nursing implications, mechanism of action, half life, administration, and more. Hazards all reactants, products, and solvents must be handled in a.
Depolarization of the neuronal membrane is inhibited, thereby blocking the initiation and conduction of nerve impulses. Synthesis of two local anesthetics from toluene acs publications. Using a magnetic stir bar stir the mixture until the solid dissolves completely. Benzocaine api dmfs us drug master file dmf details. They are used in numerous types ofsynthetic reactions, to create different products for a vast array of purposes, including medicinaland cosmetic. The format of this report book have been checked in our athabasca laboratories.
Synthesis of benzocaine lab help in this lab we used 4aminobenzoic acid, sulfuric acid, ethanol100%, and sodium bicarbonate. Synthesis and characterisation of benzocaine experiment practical report. This is an update to two previous fda drug safety communications, reports of a rare, but serious and potentially fatal adverse effect with the use of overthecounter otc benzocaine gels and. Experiment 1benzocaine 11 experiment 1 synthesis of. Americaine benzocaine is also used to numb the skin or surfaces inside the. Pdf chemical oxidative polymerization of benzocaine. How to prepare benzocaine fischer esterification with. Add a magnetic spin vane and stir the mixture until the solid dissolves completely. Synthesis and characterization of benzocaine lessons. Home synthesis of ethyl paminobenzoate benzocaine from p nitrobenzoic acid. In this experiment, the synthesis of benzocaine 2 is carried out by the acidcatalyzed esterification of. Why is the melting point of benzocaine significantly lower than aminobenzoic acid. Pdf microwaveassisted synthesis of local anaesthetic procaine. Synthesis of benzocaine in this experiment, a procedure is given for the preparation of a local anaesthetic, benzocaine ethyl aminobenzoate, by fischer esterification of paminobenzoic acid with ethanol.
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. To prepare benzocaine a local anesthetic from paminobenzoic acid and ethanol, via a fischer esterification reaction. Benzocaine is an ester and can be prepared via acidcatalyzed fisher. Benzocaine was prepared in this experiment by the direct esteri. Sciencemadness discussion board synthesis of benzocaine.
Uses, side effects, interactions, pictures, warnings density calculation. Synthesising benzocaine via reflux with a condenser. What is the purpose of adding sodium bicarbonate to raise the ph. Create marketing content that resonates with prezi video.
You can merge pdfs or a mix of pdf documents and other files. How to merge pdfs and combine pdf files adobe acrobat dc. The preparation of the local anesthetic, benzocaine. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Click add files and select the files you want to include in your pdf. Americaine benzocaine anesthetic lubricant is a local anesthetic numbing medication used to reduce pain or discomfort caused by minor skin irritations, sore throat, sunburn, teething pain, vaginal or rectal irritation, ingrown toenails, hemorrhoids, and many other sources of minor pain on a surface of the body. Show the complete reaction mechanism for the synthesis of benzocaine from paba, sulfuric acid and ethanol. Synthesis and characterization of covalently bound 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. Benzocaine binds to the sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions.
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