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{{Short description|Local anaesthetic drug}}
{{Refimprove|date=August 2009}}
{{about|the drug|other uses|Americain (disambiguation)}}
{{drugbox
{{Use mdy dates|date=September 2019}}
| verifiedrevid = 443416332
{{cs1 config |name-list-style=vanc |display-authors=6}}
| IUPAC_name = ethyl p-aminobenzoate
{{Infobox drug
| Watchedfields = changed
| verifiedrevid = 457480862
| image = Benzocaine.svg | image = Benzocaine.svg
| width = 200
| image2 = Benzocaine-from-xtal-3D-balls.png | image2 = Benzocaine-from-xtal-3D-balls.png
| width2 = 200


<!--Clinical data--> <!--Clinical data-->
| Drugs.com = {{Drugs.com|monograph|benzocaine-topical}} | Drugs.com = {{Drugs.com|monograph|benzocaine-topical}}
| tradename = Anbesol, Cepacol, Lanacane | tradename = Anbesol, Lanacane, Orajel, others
| routes_of_administration = ], ]
| pregnancy_US = C
| ATC_prefix = C05
| routes_of_administration = Topical
| ATC_suffix = AD03
| ATC_supplemental = {{ATC|D04|AB04}}, {{ATCvet|N01|AX92}}, {{ATC|N01|BA05}}, {{ATC|R02|AD01}}

| legal_US = OTC
| legal_UK = GSL, P


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
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| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 94-09-7 | CAS_number = 94-09-7
| ATC_prefix = C05
| ATC_suffix = AD03
| ATC_supplemental = {{ATC|D04|AB04}}, {{ATCvet|N01|AX92}}, {{ATC|N01|BA05}}, {{ATC|R02|AD01}}
| PubChem = 2337 | PubChem = 2337
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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<!--Chemical data--> <!--Chemical data-->
| IUPAC_name = Ethyl 4-aminobenzoate
| C=9 | H=11 | N=1 | O=2
| C=9 | H=11 | N=1 | O=2
| molecular_weight = 165.189 g/mol
| smiles = O=C(OCC)c1ccc(N)cc1 | SMILES = O=C(OCC)c1ccc(N)cc1
| InChI = 1/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3 | StdInChI = 1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
Line 49: Line 54:
| StdInChIKey = BLFLLBZGZJTVJG-UHFFFAOYSA-N | StdInChIKey = BLFLLBZGZJTVJG-UHFFFAOYSA-N
}} }}
'''Benzocaine''' is a ] commonly used as a ] pain reliever, or in cough drops. It is the active ingredient in many over-the-counter ] ointments (e.g., products for ]s of Anbesol by ], Kank-a by ], and Orabase B and Orajel by ]). It is also combined with ] to form ], (Brand name '''Auralgan''') to relieve earpain and remove ].


'''Benzocaine''', sold under the brand name '''Orajel''' amongst others, is a ], belonging to the ] ], commonly used as a ] ] or in ]s. It is the ] in many ] ] ]s such as products for ]s. It is combined with ] to form ]. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.<ref name=FDA2018>{{cite web|title=Safety Alerts for Human Medical Products - Oral Over-the-Counter Benzocaine Products: Drug Safety Communication - Risk of Serious and Potentially Fatal Blood Disorder|url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm608612.htm|website=www.fda.gov|access-date=May 26, 2018|archive-date=September 7, 2018|archive-url=https://web.archive.org/web/20180907192533/https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm608612.htm|url-status=dead}}</ref> In the European Union, the contraindication applies to children under 12 years of age.{{medical citation needed|date=September 2020}}
==Chemical properties==
Benzocaine is the ethyl ester of p-aminobenzoic acid (]); it can be prepared from PABA and ] by ] or via the reduction of ethyl p-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, ] and ]. The melting point of benzocaine is 88-90 degrees Celsius,<ref name=intpharm>{{cite web|url=http://apps.who.int/phint/en/d/Jb.6.1.62/#docfirsthighlight|title=Monographs: Pharmaceutical substances: Benzocainum - Benzocaine|publisher=The International Pharmacopoeia|accessdate=29 September 2009}}</ref> and the boiling point is about 310 degrees Celsius.<ref>D'Ans-Lax, Taschenbuch für Chemiker und Physiker, 4. Auflage, Band 2, Springer Verlag 1982, ISBN 3-540-12263-X</ref> The density of benzocaine is 1.17 g/cm<sup>3</sup>.


<!-- Society and culture -->
==History==
It was first synthesised in 1890 in Germany and approved for medical use in 1902.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=475 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA475 |language=en}}</ref>
Benzocaine was first synthesised in 1890 by a German chemist named Eduard Ritsert, in the town of ]<ref>{{cite web|url=http://www.ritsert.de/index.php?option=com_content&task=view&lang=en&id=13&Itemid=27|title=100 years of Dr. Ritsert |publisher=Dr. Ritsert Pharma|accessdate=14 March 2010}}</ref> and introduced to the market in 1902.<ref>Harry Auterhoff, Lehrbuch der pharmazeutischen Chemie, Wissenschaftliche Verlagsgesellschaft Stuttgart, 1968</ref>


==Mechanism of action== ==Medical uses==
Benzocaine is indicated to treat a variety of ]-related conditions. It may be used for:
] is caused by the stimulation of ]s. When the nerve endings are stimulated, sodium enters the ], causing depolarization of the nerve and subsequent initiation of an ]. The action potential is propagated down the nerve toward the ], which interprets this as pain. ]s of ] work as a chemical barrier, stopping the sodium entering the nerve ending.


* Local anesthesia of oral and pharyngeal mucous membranes (sore throat, cold sores, mouth ulcers, toothache, sore gums, denture irritation)<ref name="ReferenceA">AHFS Drug Information 2007. McEvoy GK, ed. Benzocaine. Bethesda, MD: American Society of Health-System Pharmacists; 2007: 2844-5.</ref>
==Side effects==
* Otic pain (earache)<ref name="ReferenceA" />
Allergic reactions occur with ester local anaesthetics (like benzocaine) because of the PABA structure.
* Surgical or procedural local anesthesia<ref>Sultan Healthcare. Topex metered spray (benzocaine 20%) prescribing information. Englewood, NJ; 2006.</ref>
* Relief of skin pain caused by ], ]s, ], <ref></ref>


Examples of ]s of benzocaine include:
Benzocaine also is a well-known cause of ]. Because it may be used in topical creams with a concentration as much as 20%, it is not difficult to administer a dose sufficient to cause this problem.


*] consists of ] and benzocaine, and is used to relieve ] and remove ].<ref>{{Cite web |title=Antipyrine-Benzocaine Otic: MedlinePlus Drug Information |url=https://medlineplus.gov/druginfo/meds/a607073.html#:~:text=Antipyrine%20and%20benzocaine%20otic%20is,class%20of%20medications%20called%20analgesics. |access-date=2023-03-28 |website=medlineplus.gov |language=en}}</ref>
==Other risks==
*] consists of menthol and benzocaine, and is used to treat ].<ref>{{Cite web |title=Cepacol Sore Throat (Benzocaine-Menthol) Mucous Membrane: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing - WebMD |url=https://www.webmd.com/drugs/2/drug-164108/cepacol-sore-throat-benzocaine-menthol-mucous-membrane/details |access-date=2023-03-28 |website=www.webmd.com |language=en}}</ref>
Over-application of oral anesthetics such as Anbesol can increase the risk of ] by relaxing the gag-reflex and allowing regurgitated stomach contents or oral secretions to enter the airway. Applying an oral anesthetic and consuming beverages before going to bed can be particularly hazardous.
* A solution of benzocaine and ] is marketed for the treatment of ]s, ]s, ]s, and other insect bites<ref></ref>
The U.S. ] notified healthcare professionals and patients that FDA continues to receive reports of ], a serious and potentially fatal adverse effect, associated with benzocaine products.<ref>http://www.drugs.com/fda/benzocaine-topical-products-gels-liquids-risk-methemoglobinemia-12941.html</ref>


==Other uses== ===Other uses===
]
Benzocaine has become the most commonly encountered sophisticated 'bulking agent' for ] in the UK.<ref>{{cite news|url=http://www.bbc.co.uk/news/magazine-11177126|title=How cutting drugs became big business |publisher=BBC |accessdate=9 September 2010|date=7 September 2010}}</ref> It is being imported in barrels, often 25 kilograms, and sold within the domestic cocaine market where it is used to at least double the weight of imported cocaine. This cocaine is often then repressed into a block and stamped with a logo to suggest it has been freshly imported to the UK from source or transit locations. Benzocaine is visually very similar to cocaine and therefore does not detract from the appearance of quality. One of the other features of this substance is that it remains within the cocaine when it is subjected to Crack manufacture and has subsequently been attributed the slang name of 'magic'. Previous less compatible and inert cutting agents are evaporated within the process and therefore expose extensive adulteration. Benzocaine increases the volume of crack produced and disguises the lower quality or purity as it binds to the cocaine becoming visually indistinguishable within the Crack. The influence of benzocaine has been a significant contributor to the remarkable price increase in high purity cocaine in the UK since 2007 and the very low street quality when sold in heavily adulterated grams.


Benzocaine is used as a key ingredient in numerous pharmaceuticals: Benzocaine is used as a key ingredient in numerous pharmaceuticals:
*Over the counter throat lozenges such as ], ].
*Some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as ] and ].
*Some previous diet products such as ].
*Some ] designed to prevent ]. Benzocaine acts to desensitize the ], and theoretically allows an ] to be maintained.<ref>{{cite news| url=http://news.bbc.co.uk/1/hi/health/2049202.stm | work=BBC News | title='Longer-lasting' condom launched | date=17 June 2002}}</ref><ref>{{cite news| url=http://www.nytimes.com/2002/12/15/magazine/15ENDU.html | work=The New York Times | first=Dwight | last=Garner | title=Endurance Condoms | date=15 December 2002}}</ref>
Benzocaine is used in ] aquaculture. The strong muscular foot which the abalone use to hold on to the rocks in the wild makes handling the animals difficult. Abalone farmers use benzocaine to mildly anaesthetise them, resulting in the animals loosening their tight grip on the substrate. This enables the farmers to more easily remove them and move them around the farm.


* Some glycerol-based ear medications for use in removing excess wax as well as relieving ear conditions such as '']'' and ].
==Misconceptions==
* Some previous diet products such as ].
* Some ] designed to prevent ]. Benzocaine largely inhibits sensitivity on the ], and can allow for an ] to be maintained longer (in a continuous act) by delaying ejaculation. Conversely, an erection will also fade faster if stimulus is interrupted.<ref>{{cite news| url=http://news.bbc.co.uk/1/hi/health/2049202.stm | work=BBC News | title='Longer-lasting' condom launched | date=June 17, 2002}}</ref><ref>{{cite news| url=https://www.nytimes.com/2002/12/15/magazine/15ENDU.html | work=The New York Times | vauthors = Garner D | title=Endurance Condoms | date=December 15, 2002}}</ref>
* Benzocaine mucoadhesive patches have been used in reducing orthodontic pain.<ref>{{cite journal | vauthors = Eslamian L, Borzabadi-Farahani A, Edini HZ, Badiee MR, Lynch E, Mortazavi A | title = The analgesic effect of benzocaine mucoadhesive patches on orthodontic pain caused by elastomeric separators, a preliminary study | journal = Acta Odontologica Scandinavica | volume = 71 | issue = 5 | pages = 1168–1173 | date = September 2013 | pmid = 23301559 | doi = 10.3109/00016357.2012.757358 | s2cid = 22561192 }}</ref>
* In Poland it is included, together with menthol and zinc oxide, in the liquid powder (not to be confused with the liquid ]) used mainly after mosquito bites. Today's ready-made Pudroderm<ref>{{cite web|title=Produkty {{!}} PUDRODERM|url=http://www.pampa.com.pl/page.php?cat=produkty&doc=pudroderm|access-date=May 9, 2014|language=pl|archive-url=https://web.archive.org/web/20161018103519/http://pampa.com.pl/page.php?cat=produkty&doc=pudroderm|archive-date=October 18, 2016|url-status=dead}}</ref> was once used there as ].


===Available forms===
In Philip K. Dick's book '']'', Jim Barris, one of the main characters attempts to extract pure cocaine out of a bottle of sunburn spray by freezing it, claiming that benzocaine is simply an industry name for ],<ref>Page 47</ref>.
Benzocaine can come in a variety of preparations including:


Oral preparations:
In reality, cocaine is significantly different from benzocaine. <ref></ref>


* Lozenges (ex. ], Mycinettes)<ref>{{cite web|url=http://www.cepacol.com/ |title=Cepacol |publisher=Cepacol.com |access-date=June 2, 2015}}</ref>{{failed verification|date=September 2020}}
==References==
* Throat Spray (ex. Ultra Chloraseptic)<ref>{{Cite web|url=https://www.medicines.org.uk/emc/product/5708/smpc|title=Ultra Chloraseptic Anaesthetic Throat Spray 0.71% - Summary of Product Characteristics (SmPC) - (eMC)|website=www.medicines.org.uk|access-date=May 5, 2018|archive-date=May 5, 2018|archive-url=https://web.archive.org/web/20180505205738/https://www.medicines.org.uk/emc/product/5708/smpc|url-status=dead}}</ref>
<references/>


Topical preparations:
==External links==
* Aerosol (ex. Topex)<ref>{{cite web|url=http://www.sultanhc.com/sw/swchannel/productcatalogcf_v2/internet/model.asp?ProductMasterID=285313&ParentID=215728&SWID=1 |title=Topex Metered Spray-Sultan Healthcare |publisher=Sultanhc.com |access-date=June 2, 2015}}</ref>{{failed verification|date=September 2020}}
* ] investigation of the possible adverse effects of benzocaine mouth and throat sprays.]
* Gel (ex. Orajel, Kank-A)<ref>{{cite web|url=http://www.orajel.com/ |title=Orajel - Oral Care for the Whole Family |publisher=Orajel.com |date=May 11, 2015 |access-date=June 2, 2015}}</ref>{{failed verification|date=September 2020}} <ref>{{Cite web |title=Kank-A {{!}} Canker Sore Treatment & Pain Relief |url=https://kank-a.com/ |access-date=2023-11-29 |language=en-US}}</ref>
* from the Chemistry Department at Oxford University.
* Paste (ex. Orabase)<ref>{{cite web|url=http://www.colgateprofessional.com/products/colgate-orabase-paste-with-benzocaine/overview |title=Colgate Orabase Paste with Benzocaine &#124; Indications &#124; Dental Products |publisher=Colgateprofessional.com |access-date=June 2, 2015}}</ref>{{failed verification|date=September 2020}}
* Cream (ex. Lanacane - active ingredient 3% Benzocaine)
Otic preparations:
* Solution (ex. Allergen)

==Side effects==
Benzocaine is generally well tolerated and non-toxic when applied topically as recommended.<ref>Lexicomp Online, Adult and Pediatric Lexi-Drugs Online, Hudson, Ohio: Lexi-Comp, Inc.; 2013; April 15, 2013.</ref>

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.<ref>{{cite web |author=U.S. Food and Drug Administration |title=FDA Public Health Advisory: Life-threatening side effects with use of skin products containing numbing ingredients for cosmetic procedures. |website=] |date=February 6, 2007 |archive-date=February 8, 2007 |archive-url=https://web.archive.org/web/20070208052946/http://www.fda.gov/cder/drug/advisory/topical_anesthetics.htm |access-date=June 13, 2024 |url=http://www.fda.gov/cder/drug/advisory/topical_anesthetics.htm |url-status=unfit}}</ref>

Overapplication of oral anesthetics such as benzocaine can increase the risk of ] by relaxing the gag-reflex and allowing regurgitated stomach contents or oral secretions to enter the airway.{{medical citation needed|date=September 2020}} Applying an oral anesthetic and consuming beverages before going to bed can be particularly hazardous.{{medical citation needed|date=September 2020}}

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 ], a disorder in which the amount of oxygen carried by the blood is greatly reduced.<ref>{{cite journal | vauthors = Shua-Haim JR, Gross JS | title = Methemoglobinemia toxicity from topical benzocaine spray | journal = Journal of the American Geriatrics Society | volume = 43 | issue = 5 | pages = 590 | date = May 1995 | pmid = 7730550 | doi = 10.1111/j.1532-5415.1995.tb06117.x | s2cid = 19563675 | doi-access = free }}</ref> This side effect is most common in children under two years of age.<ref>{{cite web |url=https://www.drugs.com/fda/benzocaine-topical-products-gels-liquids-risk-methemoglobinemia-12941.html |title=Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia |publisher=Drugs.com |access-date=March 20, 2014}}</ref> 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.<ref name="fda.gov">{{cite web|url=https://www.fda.gov/drugs/drugsafety/ucm250024.htm#safety |title=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 |publisher=Fda.gov |access-date=June 2, 2015}}</ref> 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.<ref name="fda.gov" />

Benzocaine may cause allergic reactions.<ref>{{cite web|url=http://www.bedfordhospital.nhs.uk/upload_folder/patient%20information/allergy%20to%20benzocaine.pdf|title=Allergy to Benzocaine|access-date=March 20, 2014|url-status=dead|archive-url=https://web.archive.org/web/20140320095658/http://www.bedfordhospital.nhs.uk/upload_folder/patient%20information/allergy%20to%20benzocaine.pdf|archive-date=March 20, 2014}}</ref><ref>{{cite journal | vauthors = Sidhu SK, Shaw S, Wilkinson JD | title = A 10-year retrospective study on benzocaine allergy in the United Kingdom | journal = American Journal of Contact Dermatitis | volume = 10 | issue = 2 | pages = 57–61 | date = June 1999 | pmid = 10357712 | doi = 10.1016/s1046-199x(99)90000-3 }}</ref><ref>{{cite journal | vauthors = González-Rodríguez AJ, Gutiérrez-Paredes EM, Revert Fernández Á, Jordá-Cuevas E | title = Allergic contact dermatitis to benzocaine: the importance of concomitant positive patch test results | journal = Actas Dermo-Sifiliograficas | volume = 104 | issue = 2 | pages = 156–158 | date = March 2013 | pmid = 22551703 | doi = 10.1016/j.ad.2011.07.023 | url = http://apps.elsevier.es/watermark/ctl_servlet?_f=10&pident_articulo=90193182&pident_usuario=0&pcontactid=&pident_revista=403&ty=87&accion=L&origen=cardio&web=http://www.revespcardiol.org&lan=en&fichero=403v104n02a90193182pdf001.pdf | access-date = March 20, 2014 | url-status = dead | archive-url = https://web.archive.org/web/20160303234050/http://apps.elsevier.es/watermark/ctl_servlet?_f=10&pident_articulo=90193182&pident_usuario=0&pcontactid=&pident_revista=403&ty=87&accion=L&origen=cardio&web=http%3A%2F%2Fwww.revespcardiol.org&lan=en&fichero=403v104n02a90193182pdf001.pdf | archive-date = March 3, 2016 }}</ref><ref>{{cite news| vauthors = Goldman L |url= http://www.cnn.com/2008/HEALTH/02/05/healthmag.creams/index.html?iref=newssearch |title=Go easy on medicated lotions, creams, gels |publisher=CNN |date=February 5, 2008 |access-date=March 20, 2014}}</ref> These include:
* ] (redness and itchiness)<ref name="ReferenceB">Cetylite Industries. Cetacaine (benzocaine 14%, tetracaine 2% and butamben 2%) spray, gel and liquid prescribing information. Pennsauken, NJ; 2006 Sept.</ref>
* ] (rare)<ref name="ReferenceB" />

==Pharmacology==

===Pharmacodynamics===
] is caused by the stimulation of ]s. When the ]s are stimulated, ] enters the ], causing ] of the ] and subsequent initiation of an ]. The action potential is propagated down the nerve toward the ], which interprets this as pain. Benzocaine acts to ] the ]s (VGSCs) on the ] ], stopping the propagation of the action potential.{{Citation needed|date=January 2023}}

==Chemistry==
Benzocaine is the ] ] of ] (PABA). It can be prepared from PABA and ]<ref>{{cite journal | doi = 10.1021/ed100838a | title = Synthesis of Two Local Anesthetics from Toluene: An Organic Multistep Synthesis in a Project-Oriented Laboratory Course | year = 2012 | vauthors = Demare P, Regla I | journal = Journal of Chemical Education | volume = 89 | issue = 1 | page = 147| bibcode = 2012JChEd..89..147D }}</ref> by ] or via the reduction of ethyl ''p''-nitrobenzoate. Benzocaine is sparingly soluble in water; it is more soluble in dilute acids and very soluble in ethanol, ], and ]. The ] of benzocaine is 88–92&nbsp;°C,<ref name="pubchem">{{Cite web |title= Benzocaine |url=https://pubchem.ncbi.nlm.nih.gov/compound/2337#section=Melting-Point |access-date=2023-03-27 | work = PubChem | publisher = U.S. National Library of Medicine |language=en}}</ref> and the ] is about 310&nbsp;°C.<ref>{{cite book | title = D'Ans-Lax, Taschenbuch für Chemiker und Physiker | series =Organische Verbindungen |date=1983 |publisher=Springer Verlag |location=Berlin |isbn=3-540-12263-X |edition=4th}}</ref> The ] of benzocaine is 1.17&nbsp;g/cm<sup>3</sup>.

Benzocaine is commonly found, particularly in Britain, as an additive in street ] and also as a bulking agent in "legal highs".<ref>{{cite news|url=https://www.bbc.com/news/uk-10909884|title=Drug war targets cutting agents|work=BBC News |date=August 9, 2010}}</ref> 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.<ref>{{cite news| url = http://www.economist.com/node/21560270?fsrc=scn/tw_ec/all_cut_up | title = Drug prices: All cut up : Cocaine is cheaper, but weaker | newspaper = ] | date = August 11, 2012}}</ref>
Treatment of benzocaine with hydrazine leads to aminostimil, a compound related to ].

===Synthesis===
Benzocaine can be prepared by ] using ] and ].<ref>{{Cite journal | doi = 10.1002/cber.189502802150| title = Ueber Esterbildung bei aromatischen Amidosäuren| journal = Berichte der Deutschen Chemischen Gesellschaft| volume = 28| issue = 2| pages = 1917–1923| year = 1895| vauthors = Salkowski H | url = https://zenodo.org/record/1425796}}</ref><ref>{{Cite journal | doi = 10.1002/jlac.18651350202| title = Ueber das durch Einwirkung von Jodwasserstoff auf Mannit beziehungsweise auf Melampyrin (Dulcit) entstehende β Hexyljodür und einige seiner Derivate| journal = Annalen der Chemie und Pharmacie| volume = 135| issue = 2| pages = 129–151| year = 1865| vauthors = Erlenmeyer E, Wanklyn JA | url = https://zenodo.org/record/1427245}}</ref> It can also be prepared by reduction of ethyl 4-nitrobenzoate to the ].<ref>{{Cite journal | doi = 10.1002/jlac.18983030303| title = Ueber die Verbindungen aus Benzoylchlorid oder Phtalylchlorid und den Estern der drei Oxybenzoësäuren| journal = Justus Liebig's Annalen der Chemie| volume = 303| issue = 3| pages = 274–289| year = 1898| vauthors = Limpricht H | url = https://zenodo.org/record/1427505}}</ref><ref>{{OrgSynth | vauthors = Adams R, Cohen FL |year=1928 |title=Ethyl ''p''-aminobenzoate |volume=8 |pages=66 |collvol=1 |collvolpages=240 |prep=CV1P0240}}</ref> In industrial practice, the reducing agent is usually iron and water in the presence of a little acid.<ref>{{Cite book | doi = 10.1016/S0099-5428(08)60164-1| title = Benzocaine | volume = 12| pages = 73–104| series = Analytical Profiles of Drug Substances| year = 1983| vauthors = Ali SL | publisher = Academic Press | isbn = 978-0-12-260812-4}}</ref>

==History==
Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946),<ref>Biography of Eduard Ritsert (in German): </ref> in the town of ]<ref>{{cite web|url=http://www.ritsert.de/index.php?option=com_content&task=view&lang=en&id=13&Itemid=27|title=100 years of Dr. Ritsert|publisher=Dr. Ritsert Pharma|access-date=March 14, 2010|archive-url=https://web.archive.org/web/20170909185714/http://www.ritsert.de/index.php?option=com_content&task=view&lang=en&id=13&Itemid=27|archive-date=September 9, 2017|url-status=dead}}</ref> and introduced to the market in 1902 under the name "Anästhesin".<ref>{{cite book | vauthors = Auterhoff H | title = Lehrbuch der pharmazeutischen Chemie | location = Stuttgart, Germany | publisher = Wissenschaftliche Verlagsgesellschaft | date = 1968 }}</ref><ref>{{cite journal | vauthors = Ritsert E | date = 1925 | title = Über den Werdegang des Anästhesins | trans-title = On the development of Anaesthetics | language = German | journal = Pharmazeutische Zeitung | volume = 60 | pages = 1006–1008 }} See also: {{cite journal | vauthors = Friedrich C, Klimonow M | url = http://www.pharmazeutische-zeitung.de/index.php?id=31537 | title = 150. Geburtstag: Eduard Ritsert und das Anaesthesin | archive-url = https://web.archive.org/web/20140320125425/http://www.pharmazeutische-zeitung.de/index.php?id=31537 | archive-date = 20 March 2014 | trans-title = 150th birthday: Eduard Ritsert and Anästhetsin | language = German | journal = Pharmazeutische Zeitung Online | date = December 2014 }} First published clinical study demonstrating the efficacy of benzocaine: {{cite journal | vauthors = von Noorden C | date = 1902 | title = Ueber para-Aminobenzoesäure-Ester als locales Anästhetikum | trans-title = On ester of para-aminobenzoic acid as a local anaesthetic | language = German | journal = Klinische Wochenschrift | volume = 39 | pages = 373–375 }}</ref>

==Veterinary medicine==
Bath solutions of benzocaine and its derivatives are commonly used to anesthetize ] for surgery.<ref>{{cite journal | vauthors = Guénette SA, Giroux MC, Vachon P | title = Pain perception and anaesthesia in research frogs | journal = Experimental Animals | volume = 62 | issue = 2 | pages = 87–92 | date = 2013 | pmid = 23615302 | doi = 10.1538/expanim.62.87 | doi-access = free }}</ref><ref>{{cite web|title=Amphibian Anesthesia — Research at Penn State|url=http://www.research.psu.edu/arp/anesthesia/amphibian-anesthesia.html|website=PennState Animal Resource Program|publisher=The Pennsylvania State University|access-date=August 24, 2017|location=State College, U.S.|language=en|date=November 8, 2010}}</ref> Benzocaine-based anesthetics are potent and highly effective for both anesthesia and euthanasia in amphibians.<ref>{{cite journal | vauthors = Barros AL, Lima AP, Fachin-Espinar MT, Nunez CV | title = Evaluation of benzocaine-based anesthetic gel in anuran skins extracts: A case study using the frog Lithodytes lineatus (Anura: Leptodactylidae) | journal = PLOS ONE | volume = 15 | issue = 12 | pages = e0243654 | date = 2020 | pmid = 33290419 | pmc = 7723253 | doi = 10.1371/journal.pone.0243654 | bibcode = 2020PLoSO..1543654B | doi-access = free }}</ref>

== References ==
{{Reflist}}


{{Vasoprotectives}}
{{Antipruritics}}
{{Local anesthetics}} {{Local anesthetics}}
{{Throat preparations}} {{Throat preparations}}
{{Vasoprotectives}}
{{Antipruritics}}
{{Ion channel modulators}}
{{Portal bar | Medicine}}
{{Authority control}}


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