Capitals indicate lifethreatening, underlines indicate most frequent. 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. The reaction mechanism for the synthesis of benzocaine is divided into six key steps. Free resources to assist you with your university studies. Benzocaine uses, products, precautions and alternatives.
How to prepare benzocaine fischer esterification with. Synthesising benzocaine via reflux with a condenser. Learn vocabulary, terms, and more with flashcards, games, and other study tools. The preparation of the local anesthetic, benzocaine penn state. Uses, side effects, interactions, pictures, warnings density calculation. Synthesising benzocaine via reflux with a condenser uk essays. Mohannad alashker nathan dyer william cobb dylan davies joe joiner. It is permitted for some medical use, but is otherwise outlawed. In this experiment, the synthesis of benzocaine 2 is carried out by the. May 15, 2019 cooking benzocaine into crack australia. Synthesis, characterization and antimicrobial activity of. The most common side effect of both medications is a stinging, tenderness, redness, or local skin reaction in.
Pdf chemical oxidative polymerization of benzocaine. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed. Benzocaine was prepared in this experiment by the direct esteri. Benzocaine is a topical local anesthetic thats applied to the skin, mouth or gums to numb nerve endings. The synthesis of benzocaine, a common anesthetic prelab readingvideo. Heat this mixture on a sand bath until all the solid dissolves. Synthesis and characterization of covalently bound benzocaine. Seraphim gibbons undergraduate symposium by an authorized administrator of sophia. The present invention relates to a preparation method of ethyl4dimethylaminobenzoate intermediate benzocaine ethyl4aminobenzoate.
Synthesis and characterization of benzocaine lessons tes. The preparation of the local anesthetic, benzocaine, by an. Show the detailed mechanism for the formation of benzocaine from paminobenzoic acid. 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. Apply small amount to the penis gland 1520 min before sexual intercourse. Expired lifetime application number us769285a inventor jr george m illich ralph m robinson. Benzocaine is a pain reliever and has many active overthecounter ingredients. Important key differences between benzocaine and lidocaine.
It is the active ingredient in many overthecounter anesthetic ointments such as products for oral ulcers. 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 purpose of this experiment was to synthesize benzocaine, a common topical anesthetic, via acidcatalyzed fisher esterfication of paminobenzoic acid and ethanol results and discussion. This study is focused on the synthesis of procaine from its precursor benzocaine using a green chemistry synthesis, namely solventfree.
Lidocaine is a member of the caine family of pharmaceutical local anesthetics. Benzocaine pharmacokinetic parameters of uptake, clearance, and metabolic clearance are influenced by temperature, i. Report synthesis of benzocaine please fill this form, we will try to respond as soon as possible. Pdf microwaveassisted synthesis of local anaesthetic. Metabolism, elimination, and pharmacokinetics of the fish. Ejectdelay benzocaine dosing, indications, interactions. A white, odorless, tasteless crystalline ester, c9h11no2, used as a local anesthetic. 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. Weigh approximately 150170 mg of benzocaine into a 250 ml conical flask. Benzocaine is the ethyl ester of 4aminobenzoic acid 2. 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. Preparing benzocaine is often done in a school lab setting to demonstrate the acid. Pdf synthesis, characterization and antimicrobial activity.
Benzocaine should be stored in closed bottles, away from moisture and air, if stored for long periods of time. Depolarization of the neuronal membrane is inhibited, thereby blocking the initiation and. Synthesis of ethyl paminobenzoate benzocaine from p. The classic, optimal way of benzocaine synthesis is the reduction of the nitro. 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.
Synthesis and characterisation of benzocaine experiment practical report aim. Pdf microwaveassisted synthesis of local anaesthetic procaine. It relieves pain and itching caused by conditions like insect bites, sore throats and toothaches. Benzocaine can be either oxidized with fentons reagent or poured down the drain, depending on the amount of waste you intend to dispose.
For the synthesis of benzocaine from paminobenzoic acid in sulfuric acid. 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. Synthesis of procaine february 23, 2016 december 23, 2017 organic put 9. 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. Single step synthesis of benzocaine christopher nusbaum dates performed. Synthesis, characterization and antimicrobial activity of some hetero benzocaine dervivatives article pdf available in international journal of pharmacy and pharmaceutical sciences vol. 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. The equilibrium was made to lie far to the right by using acid in excess and carrying out the. Metal and base free synthesis of primary amines via ipso amination of. 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. The immediate environment of a molecule can have a profound influence on its properties. Benzocaine binds to the sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions.
It is also combined with antipyrine to form ab otic drops to relieve ear pain and remove earwax. Synthesis and characterization of benzocaine lessons. Show the complete reaction mechanism for the synthesis of benzocaine from paba, sulfuric acid and ethanol. Synthesis and characterisation of benzocaine experiment practical report. As a counter electrode, large surface platinum plate was used. Benzocaine is a waterinsoluble estertype local anesthetic agent that is mainly useful for topical application. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses. Description download synthesis of benzocaine comments. According to escobel, 2011, aspirin is synthesized. 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.
The oxidation products of benzocaine the oxidation of benzocaine has been carried out with aps at were dissolved at a concentration of 2. Experiment nine synthesis and purification of benzocaine. Synthesis, characterization and antimicrobial activity of some hetero benzocaine dervivatives article pdf available in international journal of pharmacy and pharmaceutical sciences vol 45. Preparing benzocaine is often done in a school lab setting to demonstrate the acidcatalyzed esterification of a carboxylic. Pdf benzocaine, sold under the brand name orajel among others, is an ester local anesthetic commonly used as a topical pain. Benzocaine is the most popular cutting agent worldwide, benzocaine was used in synthesis of leteprinim.
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. A explain why paminobenzoic acid precipitates when h2so4 is added to the solution. The ethanol used was denatured, and contained about 90% ethanol by weight. Anesthetics topicalmucosal is a topic covered in the daviss drug guide. Introduction esters are important compounds in organic chemistry. Benzocaine definition of benzocaine by the free dictionary.
Sep 06, 2019 how to prepare benzocaine fischer esterification. 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. Take your hr comms to the next level with prezi video. Synthesis in a 5ml round bottom flask, add 120 mg of 4aminobenzoic acid often called paba for paminobenzoic acid, 1. Naturally occuring local anesthetics have been used for over a century to dull or alleviate the pain involved with medical procedures. C9h11no2 thesaurusantonymsrelated wordssynonymslegend. Benzocaine c9h11no2 reaction scheme for fischer esterification of paminobenzoic acid. A ester of paba and ethanol synthesis of benzocaine. A ester of paba and ethanolsynthesis of benzocaine. Apr 30, 2017 synthesis of benzocaine brought to you by. Benzocaine is a local anesthetic commonly used for pain relief. 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.
To prepare benzocaine a local anesthetic from paminobenzoic acid and ethanol, via a fischer esterification reaction. To produce an ester, one can utilize an esterification reaction. The intention of the experiment was to synthesise benzocaine, an ester, from. Use three 1ml portions of cold water to wash the product crystals from the flask onto the funnel. Benzocaine can be prepared by esterification using 4aminobenzoic acid and ethanol. Oxidation of benzocaine sce as a reference electrode. Add 10 ml of a mercuric acetate solution, and let the flask stand for 45 minutes. They are used in numerous types ofsynthetic reactions, to create different products for a vast array of purposes, including medicinaland cosmetic. 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. Lidocaine and benzocaine have very similar side effects. Reaction of ethanol with paminobenzoic acid a place 0.
Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Dried thoroughly by leaving it in an open container until the next lab, weigh it, calculate the % yield, and determine its melting point. Students undertake, in a severalweek independent project, the multistep synthesis of a pharmaceutical drug. Benzocaine is an ester and can be prepared via acidcatalyzed. Treatment of benzocaine with hydrazine leads to aminostimil a compound related to isoniazid. Synthesis and characterization of covalently bound benzocaine graphite oxide derivative. This event is brought to you for free and open access by the conferences and events at sophia.
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