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.[9][10]
Benzocaine mucoadhesive patches have been used in reducing orthodontic pain.[11]
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[12] was once used there as pharmaceutical compound.
Available formsedit
Benzocaine can come in a variety of preparations including:
Cream (ex. Lanacane - active ingredient 3% Benzocaine)
Otic preparations:
Solution (ex. Allergen)
Side effectsedit
Benzocaine is generally well tolerated and non-toxic when applied topically as recommended.[19]
However, there have been reports of serious, life-threatening adverse effects (e.g., seizures, coma, irregular heart beat, respiratory depression) with over-application of topical products or when applying topical products that contain high concentrations of benzocaine to the skin.[20]
Overapplication of oral anesthetics such as benzocaine can increase the risk of pulmonary aspiration by relaxing the gag-reflex and allowing regurgitated stomach contents or oral secretions to enter the airway.[medical citation needed] Applying an oral anesthetic and consuming beverages before going to bed can be particularly hazardous.[medical citation needed]
The topical use of higher concentration (10–20%) benzocaine products applied to the mouth or mucous membranes has been found to be a cause of methemoglobinemia, a disorder in which the amount of oxygen carried by the blood is greatly reduced.[21] This side effect is most common in children under two years of age.[22] As a result, the FDA has stated that benzocaine products should not be used in children under two years of age, unless directed by and supervised by a healthcare professional.[23] In European countries, the contraindication applies to children under 12 years of age. Symptoms of methemoglobinemia usually occur within minutes to hours of applying benzocaine, and can occur upon the first-time use or after additional use.[23]
Benzocaine may cause allergic reactions.[24][25][26][27] These include:
Benzocaine is commonly found, particularly in Britain, as an additive in street cocaine and also as a bulking agent in "legal highs".[32] Benzocaine gives a numbing effect similar to cocaine and as a bulking and binding agent it can not be detected once mixed. It is the most popular cutting agent worldwide.[33]
Treatment of benzocaine with hydrazine leads to aminostimil, a compound related to isoniazid.
Synthesisedit
Benzocaine can be prepared by esterification using 4-aminobenzoic acid and ethanol.[34][35] It can also be prepared by reduction of ethyl 4-nitrobenzoate to the amine.[36][37] In industrial practice, the reducing agent is usually iron and water in the presence of a little acid.[38]
Historyedit
Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946),[39] in the town of Eberbach[40] and introduced to the market in 1902 under the name "Anästhesin".[41][42]
Veterinary medicineedit
Bath solutions of benzocaine and its derivatives are commonly used to anesthetize amphibians for surgery.[43][44] Benzocaine-based anesthetics are potent and highly effective for both anesthesia and euthanasia in amphibians.[45]
Referencesedit
^"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. Archived from the original on September 7, 2018. Retrieved May 26, 2018.
^Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 475. ISBN 9783527607495.
^ abAHFS Drug Information 2007. McEvoy GK, ed. Benzocaine. Bethesda, MD: American Society of Health-System Pharmacists; 2007: 2844-5.
^"'Longer-lasting' condom launched". BBC News. June 17, 2002.
^Garner D (December 15, 2002). "Endurance Condoms". The New York Times.
^Eslamian L, Borzabadi-Farahani A, Edini HZ, Badiee MR, Lynch E, Mortazavi A (September 2013). "The analgesic effect of benzocaine mucoadhesive patches on orthodontic pain caused by elastomeric separators, a preliminary study". Acta Odontologica Scandinavica. 71 (5): 1168–1173. doi:10.3109/00016357.2012.757358. PMID 23301559. S2CID 22561192.
^"Produkty | PUDRODERM" (in Polish). Archived from the original on October 18, 2016. Retrieved May 9, 2014.
^"Ultra Chloraseptic Anaesthetic Throat Spray 0.71% - Summary of Product Characteristics (SmPC) - (eMC)". www.medicines.org.uk. Archived from the original on May 5, 2018. Retrieved May 5, 2018.
^"Topex Metered Spray-Sultan Healthcare". Sultanhc.com. Retrieved June 2, 2015.
^"Orajel - Oral Care for the Whole Family". Orajel.com. May 11, 2015. Retrieved June 2, 2015.
^"Colgate Orabase Paste with Benzocaine | Indications | Dental Products". Colgateprofessional.com. Retrieved June 2, 2015.
^Lexicomp Online, Adult and Pediatric Lexi-Drugs Online, Hudson, Ohio: Lexi-Comp, Inc.; 2013; April 15, 2013.
^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
^Shua-Haim JR, Gross JS (May 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. S2CID 19563675.
^"Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia". Drugs.com. Retrieved March 20, 2014.
^ ab"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.
^"Allergy to Benzocaine" (PDF). Archived from the original (PDF) on March 20, 2014. Retrieved March 20, 2014.
^Sidhu SK, Shaw S, Wilkinson JD (June 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.
^González-Rodríguez AJ, Gutiérrez-Paredes EM, Revert Fernández Á, Jordá-Cuevas E (March 2013). "Allergic contact dermatitis to benzocaine: the importance of concomitant positive patch test results" (PDF). Actas Dermo-Sifiliograficas. 104 (2): 156–158. doi:10.1016/j.ad.2011.07.023. PMID 22551703. Archived from the original (PDF) on March 3, 2016. Retrieved March 20, 2014.
^Goldman L (February 5, 2008). "Go easy on medicated lotions, creams, gels". CNN. Retrieved March 20, 2014.
^ abCetylite Industries. Cetacaine (benzocaine 14%, tetracaine 2% and butamben 2%) spray, gel and liquid prescribing information. Pennsauken, NJ; 2006 Sept.
^Demare P, Regla I (2012). "Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course". Journal of Chemical Education. 89 (1): 147. Bibcode:2012JChEd..89..147D. doi:10.1021/ed100838a.
^"Benzocaine". PubChem. U.S. National Library of Medicine. Retrieved March 27, 2023.
^D'Ans-Lax, Taschenbuch für Chemiker und Physiker. Organische Verbindungen (4th ed.). Berlin: Springer Verlag. 1983. ISBN 3-540-12263-X.
^"Drug war targets cutting agents". BBC News. August 9, 2010.
^"Drug prices: All cut up : Cocaine is cheaper, but weaker". The Economist. August 11, 2012.
^Salkowski H (1895). "Ueber Esterbildung bei aromatischen Amidosäuren". Berichte der Deutschen Chemischen Gesellschaft. 28 (2): 1917–1923. doi:10.1002/cber.189502802150.
^Erlenmeyer E, Wanklyn JA (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): 129–151. doi:10.1002/jlac.18651350202.
^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.
^Ali SL (1983). Benzocaine. Analytical Profiles of Drug Substances. Vol. 12. Academic Press. pp. 73–104. doi:10.1016/S0099-5428(08)60164-1. ISBN 978-0-12-260812-4.
^Biography of Eduard Ritsert (in German): Deutsche Biographie: Ritsert, Eduard.
^"100 years of Dr. Ritsert". Dr. Ritsert Pharma. Archived from the original on September 9, 2017. Retrieved March 14, 2010.
^Auterhoff H (1968). Lehrbuch der pharmazeutischen Chemie. Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft.
^Ritsert E (1925). "Über den Werdegang des Anästhesins" [On the development of Anaesthetics]. Pharmazeutische Zeitung (in German). 60: 1006–1008. See also: Friedrich C, Klimonow M (December 2014). "150. Geburtstag: Eduard Ritsert und das Anaesthesin" [150th birthday: Eduard Ritsert and Anästhetsin [Benzocaine]]. Pharmazeutische Zeitung online (in German). Archived from the original on March 20, 2014. First published clinical study demonstrating the efficacy of benzocaine: von Noorden C (1902). "Ueber para-Aminobenzoesäure-Ester als locales Anästhetikum" [On [an] ester of para-aminobenzoic acid as a local anaesthetic]. Klinische Wochenschrift (in German). 39: 373–375.
^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.
^"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.
^Barros AL, Lima AP, Fachin-Espinar MT, Nunez CV (2020). "Evaluation of benzocaine-based anesthetic gel in anuran skins extracts: A case study using the frog Lithodytes lineatus (Anura: Leptodactylidae)". PLOS ONE. 15 (12): e0243654. Bibcode:2020PLoSO..1543654B. doi:10.1371/journal.pone.0243654. PMC7723253. PMID 33290419.