See discussions, stats, and author profiles for this publication at: https://www.researchgate.

net/publication/337317814

Synthesis of Benzocaine; Anbesol; Cepacol; Lanacane; Orajel; Anesthesin

Article · November 2019

CITATIONS READS

0 4,971

1 author:

Aymen Labidi
École nationale supérieure de chimie de Paris
66 PUBLICATIONS   0 CITATIONS   

SEE PROFILE

Some of the authors of this publication are also working on these related projects:

Sizing of unit operations in process engineering View project

Study of the effect of temperature, pressure and initial composition on the thermodynamic equilibrium of ammonia synthesis View project

All content following this page was uploaded by Aymen Labidi on 17 November 2019.

The user has requested enhancement of the downloaded file.

CODE REF AL7CB116

ORGANIC CHEMISTRY

Synthesis of Benzocaine; Anbesol; Cepacol; Lanacane; Orajel; Anesthesin

Aymen LABIDI
INSAT, Université de Carthage, Centre Urbain Nord, BP 676, Tunis-Cedex, 1080 Tunis, Tunisia

articleinfo abstract
Article history:
Benzocaine, sold under the brand name Orajel among others, is an ester local anesthetic commonly used as a topical pain
Written 17 November 2019
reliever or in cough drops. It is the active ingredient in many over-the-counter anesthetic ointments such as products
Revised 17 November 2019 for oral ulcers. It is also combined with antipyrine to form A/B otic drops to relieve ear pain and remove earwax. It is not
Available 20 November 2019 recommended in children younger than two years old.
Keywords: It was first described in 1895 and approved for medical use in 1902
A. Benzocaine
A. Reduction
C. Nitration
D. Oxydation

1. Introduction

Benzocaine is indicated to treat a variety of pain-related conditions. It 2. Experimental details

may be used for:
2.1. Synthesis
Benzocaine can be prepared by esterification using 4-
 Local anesthesia of oral and pharyngeal mucous membranes
aminobenzoic acid and ethanol.[30][31] It can also be prepared by
(sore throat, cold sores, mouth ulcers, toothache, sore gums,
reduction of ethyl 4-nitrobenzoate to the amine.[32][33] In
denture irritation)[4]
industrial practice, the reducing agent is usually iron and water in
 Otic pain (earache)[4] the presence of a little acid
 Surgical or procedural local anesthesia

Benzocaine is used as a key ingredient in numerous pharmaceuticals:

 Some glycerol-based ear medications for use in removing excess

wax as well as relieving ear conditions such as otitis
media and swimmers ear.
 Some previous diet products such as Ayds.
 Some condoms designed to prevent premature ejaculation.
Benzocaine largely inhibits sensitivity on the penis, and can
allow for an erection to be maintained longer (in a continuous
act) by delaying ejaculation. Conversely, an erection will also
fade faster if stimulus is interrupted.[6][7]
 Benzocaine mucoadhesive patches have been used in
reducing orthodontic pain.[8]
 In Poland it is included, together with menthol and zinc oxide,
in the liquid powder (not to be confused with the liquid face
powder) used mainly after mosquito bites. Today's ready made
Pudroderm[9] was once used there as pharmaceutical
compound

n
Corresponding author. Tel.: 00216 97 53 75 01.

E-mail address aymenlabidi@insat.u-carthage.tn.

 References

1. Pubchem. "Benzocaine". pubchem.ncbi.nlm.nih.gov.

2. ^ "Safety Alerts for Human Medical Products - Oral Over-the-Counter Benzocaine Products: Drug Safety Communication - Risk of Serious and Potentially Fatal Blood
Disorder". www.fda.gov. Retrieved May 26, 2018.
3. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 475. ISBN 9783527607495.
4. ^ Jump up to:a b AHFS Drug Information 2007. McEvoy GK, ed. Benzocaine. Bethesda, MD: American Society of Health-System Pharmacists; 2007: 2844-5.
5. ^ Sultan Healthcare. Topex®metered spray (benzocaine 20%) prescribing information. Englewood, NJ; 2006.
6. ^ "'Longer-lasting' condom launched". BBC News. June 17, 2002.
7. ^ Garner, Dwight (December 15, 2002). "Endurance Condoms". The New York Times.
8. ^ Eslamian L, Borzabadi-Farahani A, Edini HZ, Badiee MR, Lynch E, Mortazavi A (2013). "The analgesic effect of benzocaine mucoadhesive patches on orthodontic pain caused by
elastomeric separators, a preliminary study". Acta Odontol Scand. 71 (5): 1168–73. doi:10.3109/00016357.2012.757358. PMID 23301559.
9. ^ "Produkty | PUDRODERM" (in Polish). Retrieved May 9, 2014.
10. ^ "Cepacol®". Cepacol.com. Retrieved June 2, 2015.
11. ^ "Ultra Chloraseptic Anaesthetic Throat Spray 0.71% - Summary of Product Characteristics (SmPC) - (eMC)". www.medicines.org.uk. Retrieved May 5, 2018.
12. ^ "Topex® Metered Spray-Sultan Healthcare". Sultanhc.com. Retrieved June 2, 2015.
13. ^ "Orajel™ - Oral Care for the Whole Family". Orajel.com. May 11, 2015. Retrieved June 2, 2015.
14. ^ "Colgate Orabase Paste with Benzocaine | Indications | Dental Products". Colgateprofessional.com. Retrieved June 2, 2015.
15. ^ Lexicomp Online, Adult and Pediatric Lexi-Drugs Online, Hudson, Ohio: Lexi-Comp, Inc.; 2013; April 15, 2013.
16. ^ Food and Drug Administration. FDA Public Health Advisory: Life-threatening side effects with use of skin products containing numbing ingredients for cosmetic
procedures. 2007 Feb 6, updated 2007 Feb 9. From FDA website
17. ^ Shua-Haim, J. R.; Gross, J. S. (1995). "Methemoglobinemia toxicity from topical benzocaine spray". Journal of the American Geriatrics Society. 43 (5): 590. doi:10.1111/j.1532-
5415.1995.tb06117.x. PMID 7730550.
18. ^ "Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia". Drugs.com. Retrieved March 20, 2014.
19. ^ Jump up to:a b "FDA Drug Safety Communication: Reports of a rare, but serious and potentially fatal adverse effect with the use of over-the-counter (OTC) benzocaine gels
and liquids applied to the gums or mouth". Fda.gov. Retrieved June 2, 2015.
20. ^ "Allergy to Benzocaine" (PDF). Archived from the original (PDF) on March 20, 2014. Retrieved March 20, 2014.
21. ^ Sidhu, S. K.; Shaw, S; Wilkinson, J. D. (1999). "A 10-year retrospective study on benzocaine allergy in the United Kingdom". American Journal of Contact Dermatitis. 10 (2): 57–
61. doi:10.1016/s1046-199x(99)90000-3. PMID 10357712.
22. ^ González-Rodríguez, A. J.; Gutiérrez-Paredes, E. M.; Revert Fernández, Á.; Jordá-Cuevas, E (2013). "Allergic contact dermatitis to benzocaine: The importance of concomitant
positive patch test results" (PDF). Actas Dermo-Sifiliográficas. 104 (2): 156–8. doi:10.1016/j.ad.2011.07.023. PMID 22551703. Retrieved March 20, 2014.
23. ^ Leslie Goldman (February 5, 2008). "Go easy on medicated lotions, creams, gels". CNN. Retrieved March 20, 2014.
24. ^ Jump up to:a b Cetylite Industries. Cetacaine® (benzocaine 14%, tetracaine 2% and butamben 2%) spray, gel and liquid prescribing information . Pennsauken, NJ; 2006
Sept.
25. ^ Demare, Patricia; Regla, Ignacio (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of
Chemical Education. 89: 147. doi:10.1021/ed100838a.
26. ^ "Monographs: Pharmaceutical substances: Benzocainum – Benzocaine". The International Pharmacopoeia. Retrieved September 29, 2009.
27. ^ D'Ans-Lax, Taschenbuch für Chemiker und Physiker, 4. Auflage, Band 2, Springer Verlag 1982, ISBN 3-540-12263-X
28. ^ "Drug war targets cutting agents". August 9, 2010 – via www.bbc.co.uk.
29. ^ "Drug prices: All cut up : Cocaine is cheaper, but weaker". The Economist. August 11, 2012.
30. ^ Salkowski, H. (1895). "Ueber Esterbildung bei aromatischen Amidosäuren" (PDF). Berichte der Deutschen Chemischen Gesellschaft. 28 (2): 1917–
1923. doi:10.1002/cber.189502802150.
31. ^ Erlenmeyer, E.; Wanklyn, J. A. (1865). "Ueber das durch Einwirkung von Jodwasserstoff auf Mannit beziehungsweise auf Melampyrin (Dulcit) entstehende β Hexyljodür und einige
seiner Derivate". Annalen der Chemie und Pharmacie. 135 (2): 129. doi:10.1002/jlac.18651350202.
32. ^ Limpricht, H. (1898). "Ueber die Verbindungen aus Benzoylchlorid oder Phtalylchlorid und den Estern der drei Oxybenzoësäuren". Justus Liebig's Annalen der
Chemie. 303 (3): 274–289. doi:10.1002/jlac.18983030303.
33. ^ Adams, Roger; Cohen, F.L. (1928). "Ethyl p-aminobenzoate". Organic Syntheses. 8: 66.; Collective Volume, 1, p. 240
34. ^ Ali, S. L. (1983). Benzocaine. Analytical Profiles of Drug Substances. 12. pp. 73–104. doi:10.1016/S0099-5428(08)60164-1. ISBN 978-0-12-260812-4.
35. ^ Biography of Eduard Ritsert (in German): Deutsche Biographie: Ritsert, Eduard .
36. ^ "100 years of Dr. Ritsert". Dr. Ritsert Pharma. Retrieved March 14, 2010.
37. ^ Harry Auterhoff, Lehrbuch der pharmazeutischen Chemie (Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft, 1968).
38. ^ Ritsert, E. (1925) "Über den Werdegang des Anästhesins" (On the development of Anästhesin), Pharmazeutische Zeitung, vol. 60, pages 1006–1008. See also: Christoph
Friedrich and Magdalena Klimonow, "150. Geburtstag: Eduard Ritsert und das Anaesthesin" (150th birthday: Eduard Ritsert and Anästhetsin
[Benzocaine]"), Pharmazeutische Zeitung online. First published clinical study demonstrating the efficacy of benzocaine: Noorden, C. v. (1902) "Ueber para-
Aminobenzoesäure-Ester als locales Anästhetikum" (On [an] ester of para-aminobenzoic acid as a local anaesthetic), Klinische Wochenschrift, vol. 39, pages 373–375.
39. ^ Guénette, SA; Giroux, MC; Vachon, P (2013). "Pain perception and anaesthesia in research frogs". Experimental Animals. 62 (2): 87–
92. doi:10.1538/expanim.62.87. PMID 23615302.
40. ^ "Amphibian Anesthesia — Research at Penn State". PennState Animal Resource Program. State College, U.S.: The Pennsylvania State University. November 8, 2010.
Retrieved August 24, 2017.
41.

View publication stats