Oxidation of benzocaine sce as a reference electrode. Oct, 2011 this article describes one of the projects in the advanced undergraduate organic chemistry laboratory course concerning the synthesis of two local anesthetic drugs, prilocaine and benzocaine, with a common threestep sequence starting from toluene. Experiment nine synthesis and purification of benzocaine. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses. Seraphim gibbons undergraduate symposium by an authorized administrator of sophia. As a counter electrode, large surface platinum plate was used. In australia, crack falls under the same category as cocaine, which is listed as a schedule 8 controlled drug, indicating that any substances and preparations for therapeutic use under this category have high potential for abuse and addiction. Synthesising benzocaine via reflux with a condenser. The ethanol used was denatured, and contained about 90% ethanol by weight. Benzocaine is a local anesthetic commonly used for pain relief. Sep 06, 2019 how to prepare benzocaine fischer esterification.
Benzocaine binds to the sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. A ester of paba and ethanolsynthesis of benzocaine. Synthesis and characterization of benzocaine lessons. How to prepare benzocaine fischer esterification with. Lidocaine is a member of the caine family of pharmaceutical local anesthetics. 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. Sciencemadness discussion board synthesis of benzocaine. Benzocaine, the ethyl ester of paraaminobenzoic acid that finds an application as a local anesthetic, is found to adopt in its protonated form at least two populations of distinct structures in the gas phase, and their relative intensities strongly depend on the properties of the solvent.
You also need to do some on your own reading of section 2015 in wade and become familiar with macroscale recrystallization and macroscale separation using a separatory funnel. Benzocaine c9h11no2 reaction scheme for fischer esterification of paminobenzoic acid. Depolarization of the neuronal membrane is inhibited, thereby blocking the initiation and. Pdf chemical oxidative polymerization of benzocaine. Transfer 100 ml of acetic acid into the flask, and dissolve the benzocaine in the acid by placing the container in an ultrasonic bath at 2025c for 23 minutes. Introduction esters are important compounds in organic chemistry. To produce an ester, one can utilize an esterification reaction. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. The oxidation products of benzocaine the oxidation of benzocaine has been carried out with aps at were dissolved at a concentration of 2. Reaction of ethanol with paminobenzoic acid a place 0. Take your hr comms to the next level with prezi video.
Preparing benzocaine is often done in a school lab setting to demonstrate the acid. Add 10 ml of a mercuric acetate solution, and let the flask stand for 45 minutes. Pdf microwaveassisted synthesis of local anaesthetic procaine. This ethyl ester of p aminobenzoic acid paba, a common sunscreen ingredient can react with compounds in sunscreens and hair dyes or produce an allergic reaction. Important key differences between benzocaine and lidocaine.
Synthesis and characterization of covalently bound benzocaine graphite oxide derivative. The onset of action is rapid benzocaine is most commonly available as a 20% aerosol spray that is easily applied to the oropharyngeal mucosa. A explain why paminobenzoic acid precipitates when h2so4 is added to the solution. Benzocaine is an ester and can be prepared via acidcatalyzed. It is permitted for some medical use, but is otherwise outlawed. Metabolism, elimination, and pharmacokinetics of the fish. Dried thoroughly by leaving it in an open container until the next lab, weigh it, calculate the % yield, and determine its melting point.
Synthesising benzocaine via reflux with a condenser uk essays. Anesthetics topicalmucosal americaine hemorrhoidal. May 15, 2019 cooking benzocaine into crack australia. Do not use for more than 2 days unless directed by clinician. It is the active ingredient in many overthecounter anesthetic ointments such as products for oral ulcers. Benzocaine can be prepared by esterification using 4aminobenzoic acid and ethanol. Uses topical pain relief of variety of conditions, including, canker sores, insect bites, hemorrhoids, poison ivy, ingrown toenails, and irritation of the mouth and gums. To prepare benzocaine a local anesthetic from paminobenzoic acid and ethanol, via a fischer esterification reaction. Description download synthesis of benzocaine comments.
Heat this mixture on a sand bath until all the solid dissolves. According to escobel, 2011, aspirin is synthesized. Synthesis, characterization and antimicrobial activity of. Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Benzocaine should be stored in closed bottles, away from moisture and air, if stored for long periods of time. Single step synthesis of benzocaine christopher nusbaum dates performed. Students undertake, in a severalweek independent project, the multistep synthesis of a pharmaceutical drug, comprising instructorguided tasks. Anesthetics topicalmucosal is a topic covered in the daviss drug guide. Benzocaine uses, products, precautions and alternatives. We chose not to use a ph buffer with ms222 as recommended by lowe 2004 because we did not detect substantial ph change during use, as measured initially by a ph meter ysi ph100. Learn vocabulary, terms, and more with flashcards, games, and other study tools. This article describes one of the projects in the advanced undergraduate organic chemistry laboratory course concerning the synthesis of two local anesthetic drugs, prilocaine and benzocaine, with a common threestep sequence starting from toluene. 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. 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.
Expired lifetime application number us769285a inventor jr george m illich ralph m robinson. Capitals indicate lifethreatening, underlines indicate most frequent. Benzocaine is a topical local anesthetic thats applied to the skin, mouth or gums to numb nerve endings. The present invention relates to a preparation method of ethyl4dimethylaminobenzoate intermediate benzocaine ethyl4aminobenzoate. 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. Students undertake, in a severalweek independent project, the multistep synthesis of a pharmaceutical drug. Benzocaine is a pain reliever and has many active overthecounter ingredients. Preparing benzocaine is often done in a school lab setting to demonstrate the acidcatalyzed esterification of a carboxylic. The classic, optimal way of benzocaine synthesis is the reduction of the nitro. C9h11no2 thesaurusantonymsrelated wordssynonymslegend. Show the detailed mechanism for the formation of benzocaine from paminobenzoic acid.
Apr 30, 2017 synthesis of benzocaine brought to you by. Weigh approximately 150170 mg of benzocaine into a 250 ml conical flask. This event is brought to you for free and open access by the conferences and events at sophia. The preparation of the local anesthetic, benzocaine, by an. Report synthesis of benzocaine please fill this form, we will try to respond as soon as possible. Pdf benzocaine, sold under the brand name orajel among others, is an ester local anesthetic commonly used as a topical pain. The preparation of the local anesthetic, benzocaine penn state. Benzocaine, a common ingredient in sunburn remedies and first aid creams, is a topical anestheticit numbs the nerve endings near the surface of the skin where it is applied. The synthesis of benzocaine, a common anesthetic prelab readingvideo.
Benzocaine definition of benzocaine by the free dictionary. A white, odorless, tasteless crystalline ester, c9h11no2, used as a local anesthetic. Us3037046a us769285a us76928558a us3037046a us 3037046 a us3037046 a us 3037046a us 769285 a us769285 a us 769285a us 76928558 a us76928558 a us 76928558a us 3037046 a us3037046 a us 3037046a authority us united states prior art keywords ethyl benzocaine nitrobenzoate solvent process prior art date 19581024 legal status the legal. They are used in numerous types ofsynthetic reactions, to create different products for a vast array of purposes, including medicinaland cosmetic. Synthesis of ethyl paminobenzoate benzocaine from p. The intention of the experiment was to synthesise benzocaine, an ester, from. Free resources to assist you with your university studies. The reaction mechanism for the synthesis of benzocaine is divided into six key steps. The equilibrium was made to lie far to the right by using acid in excess and carrying out the. The immediate environment of a molecule can have a profound influence on its properties. Benzocaine can be either oxidized with fentons reagent or poured down the drain, depending on the amount of waste you intend to dispose. Benzocaine pharmacokinetic parameters of uptake, clearance, and metabolic clearance are influenced by temperature, i. Lidocaine and benzocaine have very similar side effects. Benzocaine is the ethyl ester of 4aminobenzoic acid 2.
Benzocaine is a waterinsoluble estertype local anesthetic agent that is mainly useful for topical application. Synthesis in a 5ml round bottom flask, add 120 mg of 4aminobenzoic acid often called paba for paminobenzoic acid, 1. Pdf synthesis, characterization and antimicrobial activity. The most common side effect of both medications is a stinging, tenderness, redness, or local skin reaction in. Synthesis of procaine february 23, 2016 december 23, 2017 organic put 9. Naturally occuring local anesthetics have been used for over a century to dull or alleviate the pain involved with medical procedures. Metal and base free synthesis of primary amines via ipso amination of. 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. Pdf microwaveassisted synthesis of local anaesthetic. Benzocaine is the most popular cutting agent worldwide, benzocaine was used in synthesis of leteprinim.
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. A ester of paba and ethanol synthesis of benzocaine. Synthesis and characterization of benzocaine lessons tes. Benzocaine was prepared in this experiment by the direct esteri. Show the complete reaction mechanism for the synthesis of benzocaine from paba, sulfuric acid and ethanol. Treatment of benzocaine with hydrazine leads to aminostimil a compound related to isoniazid. Mohannad alashker nathan dyer william cobb dylan davies joe joiner. Uses, side effects, interactions, pictures, warnings density calculation. For the synthesis of benzocaine from paminobenzoic acid in sulfuric acid. Synthesis, characterization and antimicrobial activity of some hetero benzocaine dervivatives article pdf available in international journal of pharmacy and pharmaceutical sciences vol. Apply small amount to the penis gland 1520 min before sexual intercourse. Use three 1ml portions of cold water to wash the product crystals from the flask onto the funnel. Synthesis and characterization of covalently bound benzocaine.
Ejectdelay benzocaine dosing, indications, interactions. It is also combined with antipyrine to form ab otic drops to relieve ear pain and remove earwax. Synthesis and characterisation of benzocaine experiment practical report. Synthesis and characterisation of benzocaine experiment practical report aim. Synthesis, characterization and antimicrobial activity of some hetero benzocaine dervivatives article pdf available in international journal of pharmacy and pharmaceutical sciences vol 45. It relieves pain and itching caused by conditions like insect bites, sore throats and toothaches.
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