Ejectdelay benzocaine dosing, indications, interactions. Lollipacks are also ideal to give to patients for takehome, post operative topical pain. These observations could lead to the conclusion that benzocaine is no longer paminobenzoic acid. The preparation of the local anesthetic, benzocaine, by an. Benzocaine is a benzoate ester having 4aminobenzoic acid as the acid component and ethanol as the alcohol component. It relieves pain and itching caused by conditions like. Sciencemadness discussion board synthesis of benzocaine. Links to pubmed are also available for selected references. Lollicaine is a flavored topical anesthetic gel featuring rapid onset, no systemic absorption, and 15minute duration. 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. Synthesising benzocaine via reflux with a condenser. Us2628182a us161257a us16125750a us2628182a us 2628182 a us2628182 a us 2628182a us 161257 a us161257 a us 161257a us 16125750 a us16125750 a us 16125750a us 2628182 a us2628182 a us 2628182a authority us united states prior art keywords benzocaine example monolaurate hexitan propylene glycol prior art date 19500510 legal status the legal status is an. 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. Synthesis of ethyl paminobenzoate benzocaine from p.
Benzocaine is an ester of paraaminobenzoic acid, lacking the terminal diethylamino group of procaine, with anesthetic activity. Benzocaine was prepared in this experiment by the direct esteri. Get a printable copy pdf file of the complete article 789k, or click on a page image below to browse page by page. List of drug master files dmf of benzocaine active pharmaceutical ingredient api submitted to the u. The preparation of the local anesthetic, benzocaine chem. It is an ingredient in numerous commercial products for application on the skin, as well as in the ears, and mouth. Reaction number compound molar mass g mole density g cm3 refraction index1n20 d 1 4aminobenzoic acid 7 2 ethanol 46 0. Benzocaine is one of the widely used local anesthetics that act by preventing the impulse transmission along the nerve fibers. Home synthesis of ethyl paminobenzoate benzocaine from p nitrobenzoic acid. Cocaine synthesis from recreational drugs by professor. First paminobenzoic acid is produced from taking pacetotoluidide and oxidizing it with magnesium sulfate. Commons is a freely licensed media file repository. How to prepare benzocaine fischer esterification with.
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. Depolarization of the neuronal membrane is inhibited. According to escobel, 2011, aspirin is synthesized through the. Refer to the structure of procaine in the table in the above introduction, local anesthetics. In this experiment, the synthesis of benzocaine 2 is carried out by the acidcatalyzed esterification of 4aminobenzoic 1 acid with ethanol. Synthesis, characterization and antimicrobial activity of some hetero benzocaine dervivatives article pdf available in international journal of pharmacy and pharmaceutical sciences vol 45. Single step synthesis of benzocaine christopher nusbaum dates performed. I couldnt imagine anyone abusing benzocaine, although swirx has heard benzocaine cut cocaine is often mistaken for being higher quality then the real deal by most inexperienced in the trade due to its strong local anesthetic properties. 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 %. Synthesis, characterization and antimicrobial activity of.
The oxidation products of benzocaine the oxidation of benzocaine has been carried out with aps at were dissolved at a concentration of 2. In this video, i am synthesizing benzocaine, and explaining how the process was planned. Information from its description page there is shown below. Pdf microwaveassisted synthesis of local anaesthetic procaine. What do they cut cocaine with so it will not cook into crack. Hazards all reactants, products, and solvents must be handled in a. Synthesis of benzocaine lab help in this lab we used 4aminobenzoic acid, sulfuric acid, ethanol100%, and sodium bicarbonate. Benzocaine is a waterinsoluble estertype local anesthetic agent that is mainly useful for topical application. Remote work advice from the largest allremote company. Lollicaine is packaged in singledose lollipacks for maximum asepsis and ease of use.
What do you put in the round bottom flask prior to starting the reaction. Introduction esters are important compounds in organic chemistry. Pdf microwaveassisted synthesis of local anaesthetic. Experiment nine synthesis and purification of benzocaine. Report synthesis of benzocaine please fill this form, we will try to respond as soon as possible. Lolicaine topical anesthetic gelliquid 20% benzocaine. Can you get a contact high from cooking crack cocaine. The preparation of the local anesthetic, benzocaine, by an esterification reaction.
The risk may be increased in children younger than 2 years of age, elderly patients, or patients with. As a counter electrode, large surface platinum plate was used. The ethanol used was denatured, and contained about 90% ethanol by weight. This study is focused on the synthesis of procaine from its precursor benzocaine using a green chemistry synthesis, namely solventfree. 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 status is an. Synthesis of ethyl paminobenzoate benzocaine from p nitrobenzoic acid. Synthesis of benzocaine quiz synthesis of benzocaine. Chemistry 3720 benzene synthesis problems key provide an efficient synthesis of each of the following substituted benzenes from benzene itself. Description download synthesis of benzocaine comments.
Use any of the reagents seen in chemistry 37193720 so far and pay careful attention to the order of steps. Synthesis and characterisation of benzocaine experiment practical report. Apply basic techniques of organic synthesis to the preparation of drugs. Risk of serious and potentially fatal blood disorder prompts fda action on oral overthecounter benzocaine products used for teething and mouth pain and prescription local anesthetics. Benzocaine oral, oromucosal advanced patient information. Pdf chemical oxidative polymerization of benzocaine. Benzocaine is a topical local anesthetic thats applied to the skin, mouth or gums to numb nerve endings. What is the purpose of adding sodium bicarbonate to raise the ph. Expt 86 the preparation of the local anesthetic, benzocaine, by an esterification reaction adapted by r. They are used in numerous the mechanism of the fischer esterification that was utilized to produce benzocaine is verystraightforward carbonyl. They are used in numerous types ofsynthetic reactions, to create different products for a vast array of purposes, including medicinaland cosmetic.
Preparing benzocaine is often done in a school lab setting to demonstrate the acidcatalyzed esterification of. I think they are getting more people to try this deadly legal high by labeling it this rather then a not so. Naturally occuring local anesthetics have been used for over a century to dull or alleviate the pain involved with medical procedures. A threestep synthesis is used to create benzocaine. Why is the melting point of benzocaine significantly lower than aminobenzoic acid. The preparation of the practicals was thoroughly explained in the organic chemistry laboratory manual year 2 but lets. Benzocaine api dmfs us drug master file dmf details. Full text full text is available as a scanned copy of the original print version.
Treatment of benzocaine with hydrazine leads to aminostimil a compound related to isoniazid. Benzocaine is a weak local anesthetic and has been used primarily as an external pain reliever. In 1903 he patented his formula, and founded a company to manufacture and sell it. All structured data from the file and property namespaces is available under the creative commons cc0 license.
Pdf benzocaine, sold under the brand name orajel among others, is an ester local anesthetic commonly used as a topical pain reliever or in. 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. Benzocaine binds to the sodium channel and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Oxidation of benzocaine sce as a reference electrode. 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. Files are available under licenses specified on their description page.
To prepare benzocaine a local anesthetic from paminobenzoic acid and ethanol, via a fischer esterification reaction. 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. Show the complete reaction mechanism for the synthesis of benzocaine from paba, sulfuric acid and ethanol. This document was uploaded by user and they confirmed that. Benzocaine may cause a rare, but serious blood problem called methemoglobinemia. Students undertake, in a severalweek independent project, the multistep synthesis of a pharmaceutical drug, comprising instructorguided tasks. This condition may occur after use of the spray for medical procedures or use of the overthecounter gel or liquid for mouth sores or teething in children. Aug 22, 2010 our investigators watched one dealer wash benzocaine into rocks of. Benzocaine is an ester and can be prepared via acidcatalyzed fisher.
When the solution turns completely clear inject 4 ml of 70% sodium ethoxide in ethanol. It seems we were successful in producing benzocaine by esterification based on results of melting point, ir spectroscopy, and tlc analysis. Synthesis of benzocainelocal anaesthetic with the yield. The melting point we received was within the range of the known melting point. 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. Benzocaine is an ester and can be prepared via acidcatalyzed fisher esterfication from paminobenzoic acid and ethanol, both of which are readily available starting materials. Benzocaine uses, products, precautions and alternatives. Benzocaine is the most popular cutting agent worldwide, benzocaine was used in synthesis of leteprinim. Benzocaine is a local anesthetic commonly used for pain relief. Benzocaine can be prepared by esterification using 4aminobenzoic acid and ethanol. Antimicrobial properties of topical anesthetic liquids. This aug 2004 static snapshot is hosted by erowid as of may 2005 and is not being updated. Benzocaine is the common name of ethyl aminobenzoate, normally prepared by acid catalyzed esterification. Risk of serious and potentially fatal blood disorder.
1085 160 1339 873 696 1065 1560 414 1156 1605 859 1461 1393 287 246 318 1635 1359 352 217 1221 1243 519 261 959 1036 955 296 1083 453 448 2 846 274 271 249 457 1186 130 1098 694 625 329 608 1120 1122 1333