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Wikipedia

Benzocaine

January 11, 2023

"Americaine" redirects here. For other uses, see Americain (disambiguation).

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. It is the active ingredient in many over-the-counter anesthetic ointments such as products for oral ulcers. It is also combined with antipyrine to form A/B otic drops to relieve ear pain and remove earwax. In the US, products containing benzocaine for oral application are contraindicated in children younger than two years old.[1] In the European Union, the contraindication applies to children under 12 years of age.[medical citation needed]

Benzocaine
Clinical data
Trade namesAnbesol, Lanacane, Orajel, others
AHFS/Drugs.comMonograph
Routes of
administration		Topical, Oral
ATC code
Legal status
Legal status
  • UK: GSL, P
  • US: OTC
Identifiers
  • Ethyl 4-aminobenzoate
CAS Number
  • 94-09-7 Y
PubChem CID
  • 2337
DrugBank
  • DB01086 Y
ChemSpider
  • 13854242 Y
UNII
  • U3RSY48JW5
KEGG
  • D00552 Y
ChEBI
  • CHEBI:116735 Y
ChEMBL
  • ChEMBL278172 Y
CompTox Dashboard (EPA)
  • DTXSID8021804
ECHA InfoCard100.002.094
Chemical and physical data
FormulaC9H11NO2
Molar mass165.192 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(OCC)c1ccc(N)cc1
  • InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3 Y
  • Key:BLFLLBZGZJTVJG-UHFFFAOYSA-N Y
  (verify)

It was first synthesised in 1890 in Germany and approved for medical use in 1902.[2]

Medical uses

Benzocaine is indicated to treat a variety of pain-related conditions. It may be used for:

  • Local anesthesia of oral and pharyngeal mucous membranes (sore throat, cold sores, mouth ulcers, toothache, sore gums, denture irritation)[3]
  • Otic pain (earache)[3]
  • Surgical or procedural local anesthesia[4]

Other uses

 
Jiffy Toothache Drops bottle (7.75% Benzocaine)

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.[5][6]
  • Benzocaine mucoadhesive patches have been used in reducing orthodontic pain.[7]
  • 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[8] was once used there as pharmaceutical compound.

Available forms

Benzocaine can come in a variety of preparations including:

Oral preparations:

Topical preparations:

Otic preparations:

  • Solution (ex. Allergen)

Side effects

Benzocaine is generally well tolerated and non-toxic when applied topically as recommended.[14]

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.[15]

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.[16] This side effect is most common in children under two years of age.[17] 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.[18] 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.[18]

Benzocaine may cause allergic reactions.[19][20][21][22] These include:

Pharmacology

Pharmacodynamics

Pain is caused by the stimulation of free nerve endings. When the nerve endings are stimulated, sodium enters the neuron, causing depolarization of the nerve and subsequent initiation of an action potential. The action potential is propagated down the nerve toward the central nervous system, which interprets this as pain. Benzocaine acts to inhibit the voltage-dependent sodium channels (VDSCs) on the neuron membrane, stopping the propagation of the action potential.

Chemistry

Benzocaine is the ethyl ester of p-aminobenzoic acid (PABA). It can be prepared from PABA and ethanol[24] by Fischer esterification 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, chloroform, and ethyl ether. The melting point of benzocaine is 88–90 °C,[25] and the boiling point is about 310 °C.[26] The density of benzocaine is 1.17 g/cm3.

Benzocaine is commonly found, particularly in Britain, as an additive in street cocaine and also as a bulking agent in "legal highs".[27] Whilst giving a numbing effect similar to cocaine, users prefer Benzocaine as it is a better bulking and binding agent that can't be detected once mixed. Benzocaine is the most popular cutting agent worldwide.[28] Treatment of benzocaine with hydrazine leads to aminostimil, a compound related to isoniazid.

Synthesis

Benzocaine can be prepared by esterification using 4-aminobenzoic acid and ethanol.[29][30] It can also be prepared by reduction of ethyl 4-nitrobenzoate to the amine.[31][32] In industrial practice, the reducing agent is usually iron and water in the presence of a little acid.[33]

History

Benzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert (1859–1946),[34] in the town of Eberbach[35] and introduced to the market in 1902 under the name "Anästhesin".[36][37]

Veterinary medicine

A bath solution of benzocaine has been used to anesthetize amphibians for surgery.[38][39]

References

  1. ^ . www.fda.gov. Archived from the original on September 7, 2018. Retrieved May 26, 2018.
  2. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 475. ISBN 9783527607495.
  3. ^ a b AHFS Drug Information 2007. McEvoy GK, ed. Benzocaine. Bethesda, MD: American Society of Health-System Pharmacists; 2007: 2844-5.
  4. ^ Sultan Healthcare. Topex metered spray (benzocaine 20%) prescribing information. Englewood, NJ; 2006.
  5. ^ "'Longer-lasting' condom launched". BBC News. June 17, 2002.
  6. ^ Garner, Dwight (December 15, 2002). "Endurance Condoms". The New York Times.
  7. ^ 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. S2CID 22561192.
  8. ^ (in Polish). Archived from the original on October 18, 2016. Retrieved May 9, 2014.
  9. ^ "Cepacol". Cepacol.com. Retrieved June 2, 2015.
  10. ^ . www.medicines.org.uk. Archived from the original on May 5, 2018. Retrieved May 5, 2018.
  11. ^ "Topex Metered Spray-Sultan Healthcare". Sultanhc.com. Retrieved June 2, 2015.
  12. ^ "Orajel - Oral Care for the Whole Family". Orajel.com. May 11, 2015. Retrieved June 2, 2015.
  13. ^ "Colgate Orabase Paste with Benzocaine | Indications | Dental Products". Colgateprofessional.com. Retrieved June 2, 2015.
  14. ^ Lexicomp Online, Adult and Pediatric Lexi-Drugs Online, Hudson, Ohio: Lexi-Comp, Inc.; 2013; April 15, 2013.
  15. ^ 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
  16. ^ 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.
  17. ^ "Benzocaine Topical Products: Sprays, Gels and Liquids – Risk of Methemoglobinemia". Drugs.com. Retrieved March 20, 2014.
  18. ^ 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.
  19. ^ (PDF). Archived from the original (PDF) on March 20, 2014. Retrieved March 20, 2014.
  20. ^ 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.
  21. ^ González-Rodríguez, A. J.; Gutiérrez-Paredes, E. M.; Revert Fernández, Á.; Jordá-Cuevas, E (2013). (PDF). Actas Dermo-Sifiliográficas. 104 (2): 156–8. doi:10.1016/j.ad.2011.07.023. PMID 22551703. Archived from the original (PDF) on March 3, 2016. Retrieved March 20, 2014.
  22. ^ Leslie Goldman (February 5, 2008). "Go easy on medicated lotions, creams, gels". CNN. Retrieved March 20, 2014.
  23. ^ a b Cetylite Industries. Cetacaine (benzocaine 14%, tetracaine 2% and butamben 2%) spray, gel and liquid prescribing information. Pennsauken, NJ; 2006 Sept.
  24. ^ 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 (1): 147. Bibcode:2012JChEd..89..147D. doi:10.1021/ed100838a.
  25. ^ "Monographs: Pharmaceutical substances: Benzocainum – Benzocaine". The International Pharmacopoeia. Retrieved September 29, 2009.[dead link]
  26. ^ D'Ans-Lax, Taschenbuch für Chemiker und Physiker, 4. Auflage, Band 2, Springer Verlag 1982, ISBN 3-540-12263-X
  27. ^ "Drug war targets cutting agents". August 9, 2010 – via www.bbc.co.uk.
  28. ^ "Drug prices: All cut up : Cocaine is cheaper, but weaker". The Economist. August 11, 2012.
  29. ^ Salkowski, H. (1895). "Ueber Esterbildung bei aromatischen Amidosäuren". Berichte der Deutschen Chemischen Gesellschaft. 28 (2): 1917–1923. doi:10.1002/cber.189502802150.
  30. ^ 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.
  31. ^ 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.
  32. ^ Adams, Roger & Cohen, F.L. (1928). "Ethyl p-aminobenzoate". Organic Syntheses. 8: 66.; Collective Volume, vol. 1, p. 240
  33. ^ Ali, S. L. (1983). Benzocaine. Analytical Profiles of Drug Substances. Vol. 12. pp. 73–104. doi:10.1016/S0099-5428(08)60164-1. ISBN 978-0-12-260812-4.
  34. ^ Biography of Eduard Ritsert (in German): Deutsche Biographie: Ritsert, Eduard.
  35. ^ . Dr. Ritsert Pharma. Archived from the original on September 9, 2017. Retrieved March 14, 2010.
  36. ^ Harry Auterhoff, Lehrbuch der pharmazeutischen Chemie (Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft, 1968).
  37. ^ 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" March 20, 2014, at the Wayback Machine (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.
  38. ^ 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.
  39. ^ "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.

External links

  • "Benzocaine". Drug Information Portal. U.S. National Library of Medicine.

January 11, 2023
benzocaine, americaine, redirects, here, other, uses, americain, disambiguation, sold, under, brand, name, orajel, amongst, others, ester, local, anesthetic, commonly, used, topical, pain, reliever, cough, drops, active, ingredient, many, over, counter, anesth. Americaine redirects here For other uses see Americain disambiguation 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 It is the active ingredient in many over the counter anesthetic ointments such as products for oral ulcers It is also combined with antipyrine to form A B otic drops to relieve ear pain and remove earwax In the US products containing benzocaine for oral application are contraindicated in children younger than two years old 1 In the European Union the contraindication applies to children under 12 years of age medical citation needed BenzocaineClinical dataTrade namesAnbesol Lanacane Orajel othersAHFS Drugs comMonographRoutes ofadministrationTopical OralATC codeC05AD03 WHO D04AB04 WHO QN01AX92 WHO N01BA05 WHO R02AD01 WHO Legal statusLegal statusUK GSL P US OTCIdentifiersIUPAC name Ethyl 4 aminobenzoateCAS Number94 09 7 YPubChem CID2337DrugBankDB01086 YChemSpider13854242 YUNIIU3RSY48JW5KEGGD00552 YChEBICHEBI 116735 YChEMBLChEMBL278172 YCompTox Dashboard EPA DTXSID8021804ECHA InfoCard100 002 094Chemical and physical dataFormulaC 9H 11N O 2Molar mass165 192 g mol 13D model JSmol Interactive imageSMILES O C OCC c1ccc N cc1InChI InChI 1S C9H11NO2 c1 2 12 9 11 7 3 5 8 10 6 4 7 h3 6H 2 10H2 1H3 YKey BLFLLBZGZJTVJG UHFFFAOYSA N Y verify It was first synthesised in 1890 in Germany and approved for medical use in 1902 2 Contents 1 Medical uses 1 1 Other uses 1 2 Available forms 2 Side effects 3 Pharmacology 3 1 Pharmacodynamics 4 Chemistry 4 1 Synthesis 5 History 6 Veterinary medicine 7 References 8 External linksMedical uses EditBenzocaine is indicated to treat a variety of pain related conditions It may be used for Local anesthesia of oral and pharyngeal mucous membranes sore throat cold sores mouth ulcers toothache sore gums denture irritation 3 Otic pain earache 3 Surgical or procedural local anesthesia 4 Other uses Edit Jiffy Toothache Drops bottle 7 75 Benzocaine 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 5 6 Benzocaine mucoadhesive patches have been used in reducing orthodontic pain 7 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 8 was once used there as pharmaceutical compound Available forms Edit Benzocaine can come in a variety of preparations including Oral preparations Lozenges ex Cepacol Mycinettes 9 failed verification Throat Spray ex Ultra Chloraseptic 10 Topical preparations Aerosol ex Topex 11 failed verification Gel ex Orajel 12 failed verification Paste ex Orabase 13 failed verification Cream ex Lanacane active ingredient 3 Benzocaine Otic preparations Solution ex Allergen Side effects EditBenzocaine is generally well tolerated and non toxic when applied topically as recommended 14 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 15 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 16 This side effect is most common in children under two years of age 17 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 18 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 18 Benzocaine may cause allergic reactions 19 20 21 22 These include Contact dermatitis redness and itchiness 23 Anaphylaxis rare 23 Pharmacology EditPharmacodynamics Edit Pain is caused by the stimulation of free nerve endings When the nerve endings are stimulated sodium enters the neuron causing depolarization of the nerve and subsequent initiation of an action potential The action potential is propagated down the nerve toward the central nervous system which interprets this as pain Benzocaine acts to inhibit the voltage dependent sodium channels VDSCs on the neuron membrane stopping the propagation of the action potential Chemistry EditBenzocaine is the ethyl ester of p aminobenzoic acid PABA It can be prepared from PABA and ethanol 24 by Fischer esterification 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 chloroform and ethyl ether The melting point of benzocaine is 88 90 C 25 and the boiling point is about 310 C 26 The density of benzocaine is 1 17 g cm3 Benzocaine is commonly found particularly in Britain as an additive in street cocaine and also as a bulking agent in legal highs 27 Whilst giving a numbing effect similar to cocaine users prefer Benzocaine as it is a better bulking and binding agent that can t be detected once mixed Benzocaine is the most popular cutting agent worldwide 28 Treatment of benzocaine with hydrazine leads to aminostimil a compound related to isoniazid Synthesis Edit Benzocaine can be prepared by esterification using 4 aminobenzoic acid and ethanol 29 30 It can also be prepared by reduction of ethyl 4 nitrobenzoate to the amine 31 32 In industrial practice the reducing agent is usually iron and water in the presence of a little acid 33 History EditBenzocaine was first synthesized in 1890 by the German chemist Eduard Ritsert 1859 1946 34 in the town of Eberbach 35 and introduced to the market in 1902 under the name Anasthesin 36 37 Veterinary medicine EditA bath solution of benzocaine has been used to anesthetize amphibians for surgery 38 39 References Edit 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 Jnos Ganellin C Robin 2006 Analogue based Drug Discovery John Wiley amp Sons p 475 ISBN 9783527607495 a b AHFS Drug Information 2007 McEvoy GK ed Benzocaine Bethesda MD American Society of Health System Pharmacists 2007 2844 5 Sultan Healthcare Topex metered spray benzocaine 20 prescribing information Englewood NJ 2006 Longer lasting condom launched BBC News June 17 2002 Garner Dwight December 15 2002 Endurance Condoms The New York Times 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 S2CID 22561192 Produkty PUDRODERM in Polish Archived from the original on October 18 2016 Retrieved May 9 2014 Cepacol Cepacol com Retrieved June 2 2015 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 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 Benzocaine Topical Products Sprays Gels and Liquids Risk of Methemoglobinemia Drugs com Retrieved March 20 2014 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 Allergy to Benzocaine PDF Archived from the original PDF on March 20 2014 Retrieved March 20 2014 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 Gonzalez Rodriguez A J Gutierrez Paredes E M Revert Fernandez A Jorda Cuevas E 2013 Allergic contact dermatitis to benzocaine The importance of concomitant positive patch test results PDF Actas Dermo Sifiliograficas 104 2 156 8 doi 10 1016 j ad 2011 07 023 PMID 22551703 Archived from the original PDF on March 3 2016 Retrieved March 20 2014 Leslie Goldman February 5 2008 Go easy on medicated lotions creams gels CNN Retrieved March 20 2014 a b Cetylite Industries Cetacaine benzocaine 14 tetracaine 2 and butamben 2 spray gel and liquid prescribing information Pennsauken NJ 2006 Sept 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 1 147 Bibcode 2012JChEd 89 147D doi 10 1021 ed100838a Monographs Pharmaceutical substances Benzocainum Benzocaine The International Pharmacopoeia Retrieved September 29 2009 dead link D Ans Lax Taschenbuch fur Chemiker und Physiker 4 Auflage Band 2 Springer Verlag 1982 ISBN 3 540 12263 X Drug war targets cutting agents August 9 2010 via www bbc co uk Drug prices All cut up Cocaine is cheaper but weaker The Economist August 11 2012 Salkowski H 1895 Ueber Esterbildung bei aromatischen Amidosauren Berichte der Deutschen Chemischen Gesellschaft 28 2 1917 1923 doi 10 1002 cber 189502802150 Erlenmeyer E Wanklyn J A 1865 Ueber das durch Einwirkung von Jodwasserstoff auf Mannit beziehungsweise auf Melampyrin Dulcit entstehende b Hexyljodur und einige seiner Derivate Annalen der Chemie und Pharmacie 135 2 129 doi 10 1002 jlac 18651350202 Limpricht H 1898 Ueber die Verbindungen aus Benzoylchlorid oder Phtalylchlorid und den Estern der drei Oxybenzoesauren Justus Liebig s Annalen der Chemie 303 3 274 289 doi 10 1002 jlac 18983030303 Adams Roger amp Cohen F L 1928 Ethyl p aminobenzoate Organic Syntheses 8 66 Collective Volume vol 1 p 240 Ali S L 1983 Benzocaine Analytical Profiles of Drug Substances Vol 12 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 Harry Auterhoff Lehrbuch der pharmazeutischen Chemie Stuttgart Germany Wissenschaftliche Verlagsgesellschaft 1968 Ritsert E 1925 Uber den Werdegang des Anasthesins On the development of Anasthesin Pharmazeutische Zeitung vol 60 pages 1006 1008 See also Christoph Friedrich and Magdalena Klimonow 150 Geburtstag Eduard Ritsert und das Anaesthesin Archived March 20 2014 at the Wayback Machine 150th birthday Eduard Ritsert and Anasthetsin Benzocaine Pharmazeutische Zeitung online First published clinical study demonstrating the efficacy of benzocaine Noorden C v 1902 Ueber para Aminobenzoesaure Ester als locales Anasthetikum On an ester of para aminobenzoic acid as a local anaesthetic Klinische Wochenschrift vol 39 pages 373 375 Guenette 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 External links Edit Benzocaine Drug Information Portal U S National Library of Medicine Portal Medicine Retrieved from https en wikipedia org w index php title Benzocaine amp oldid 1129010872, wikipedia, wiki, book, books, library,

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