Editing Procaine (section)

{{Short description|Local anesthetic drug}}
{{Redirect-distinguish|Allocaine|List of cocaine analogues#Analogs sensu stricto{{!}}Allococaine}}
{{Redirect|Novocaine}}
{{Drugbox| Verifiedfields = changed
| verifiedrevid = 420414847
| IUPAC_name = 2-(diethylamino)ethyl 4-aminobenzoate
| image = procaine.svg
| image_class = skin-invert-image
| image2 = Procaine-3D-xray.png

<!--Clinical data-->
| Drugs.com = {{drugs.com|monograph|novocain}}
| pregnancy_AU = B2
| pregnancy_US = C
| legal_AU = S4
| routes_of_administration = [[wikt:parenteral|Parenteral]]

<!--Pharmacodynamic data-->
| bioavailability = N/A
| metabolism = [[Hydrolysis]] by plasma esterases
| elimination_half-life = 40–84 seconds
| excretion = [[Kidney|Renal]]

<!--Identifiers-->
<!--| CASNo_Ref = {{cascite|correct|CAS}}-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 59-46-1
| ATC_prefix = N01
| ATC_suffix = BA02
| ATC_supplemental = {{ATC|C05|AD05}} {{ATC|S01|HA05}}
| PubChem = 4914
| IUPHAR_ligand = 4291
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB00721
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4745
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 4Z8Y51M438
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08422
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 8430
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 569
| NIAID_ChemDB = 019136

<!--Chemical data-->
| C=13 | H=20 | N=2 | O=2
| smiles = O=C(OCCN(CC)CC)c1ccc(N)cc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H20N2O2/c1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11/h5-8H,3-4,9-10,14H2,1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MFDFERRIHVXMIY-UHFFFAOYSA-N
}}

'''Procaine''' is a [[local anesthetic]] drug of the [[amino esters|amino ester]] group. It is most commonly used in [[dentistry|dental procedures]] to numb the area around a tooth<ref name=denistryismain>{{cite news|url=https://www.medicalnewstoday.com/articles/321880|title=How long does numbness last after the dentist?|publisher=Medical News Today|date=May 22, 2018|access-date=July 14, 2020}}</ref> and is also used to reduce the pain of [[intramuscular injection]] of [[penicillin]]. Owing to the ubiquity of the [[trade name]] '''Novocain''' (without the "e" in the original German patent) or '''Novocaine''' (with the "e" in the US patent), in some regions, procaine is referred to [[Generic trademark|generically]] as '''novocaine'''. It acts mainly as a [[sodium channel blocker]].<ref>{{cite web | url = http://www.drugbank.ca/drugs/DB00721 | work = DrugBank | title = Procaine (DB00721) | date = 2009-06-23 }}</ref> Today, it is used therapeutically in some countries due to its [[sympatholytic]], [[anti-inflammatory]], [[perfusion]]-enhancing, and [[Mood disorder|mood-enhancing]] effects.<ref>{{cite journal | vauthors = Hahn-Godeffroy JD | title = Procain-Reset: Ein Therapiekonzept zur Behandlung chronischer Erkrankungen. | trans-title = Procaine reset: A therapy concept for the treatment of chronic diseases. | journal = Schweizerische Zeitschrift für Ganzheitsmedizin | trans-journal = [[Swiss Journal of Integrative Medicine]] | language = de | date = 2011 | volume = 23 | issue = 5 | pages = 291–6 | doi =  10.1159/000332021 | doi-access = free }}</ref>

Procaine was first synthesized in 1905,<ref>{{cite book | vauthors = Ritchie JM, Greene NM | veditors = Gilman AG, Rall TW, Nies AS, Taylor P | title = Goodman and Gilman's The Pharmacological Basis of Therapeutics |chapter=Local Anesthetics | page = [https://archive.org/details/goodmangilmansphe8good/page/311 311] |edition=8th |publisher=Pergamon Press |location=New York |year=1990 |isbn=0-08-040296-8 |chapter-url-access=registration |chapter-url=https://archive.org/details/goodmangilmansphe8good |url= https://archive.org/details/goodmangilmansphe8good | url-access = registration }}</ref> shortly after [[amylocaine]].<ref>{{cite web | vauthors = Minard R | url = http://courses.chem.psu.edu/chem36/SynFa06Web/Expt86.pdf | title = The Preparation of the Local Anesthetic, Benzocaine, by an Esterification Reaction | quote = Adapted from ''Introduction to Organic Laboratory Techniques: A Microscale Approach'', Pavia, Lampman, Kriz & Engel, 1989. | date = 18 October 2006 | access-date = 10 March 2011 | archive-url = https://web.archive.org/web/20110720030826/http://courses.chem.psu.edu/chem36/SynFa06Web/Expt86.pdf | archive-date = 20 July 2011 | url-status = dead }}</ref> It was created by the chemist [[Alfred Einhorn]] who gave the chemical the trade name Novocain, from the [[Latin]] ''nov-'' (meaning "new") and ''-caine'', a common ending for [[alkaloid]]s used as anesthetics. It was introduced into medical use by surgeon [[Heinrich Braun]].

Prior to the discovery of [[amylocaine]] and procaine, [[cocaine]] was a commonly used local anesthetic.<ref name="Ruetsch_2001">{{cite journal | vauthors = Ruetsch YA, Böni T, Borgeat A | title = From cocaine to ropivacaine: the history of local anesthetic drugs | journal = Current Topics in Medicinal Chemistry | volume = 1 | issue = 3 | pages = 175–82 | date = August 2001 | pmid = 11895133 | doi = 10.2174/1568026013395335 }}</ref> Einhorn wished his new discovery to be used for amputations, but for this surgeons preferred [[general anesthesia]]. Dentists, however, found it very useful.<ref>{{cite journal| vauthors = Drucker P |title=The discipline of innovation|journal=Harvard Business Review|date=May 1985|volume=3|issue=3|page=68 |pmid=10272260| url = https://hbr.org/2002/08/the-discipline-of-innovation }}</ref>