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mw-list-item"><a href="https://cy.wikipedia.org/wiki/Cloroprocain" title="Cloroprocain – Welsh" lang="cy" hreflang="cy" data-title="Cloroprocain" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target"><span>Cymraeg</span></a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%DA%A9%D9%84%D8%B1%D9%88%D9%BE%D8%B1%D9%88%DA%A9%D8%A7%D8%A6%DB%8C%D9%86" title="کلروپروکائین – Persian" lang="fa" hreflang="fa" data-title="کلروپروکائین" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target"><span>فارسی</span></a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Chloroproca%C3%AFne" title="Chloroprocaïne – French" lang="fr" hreflang="fr" data-title="Chloroprocaïne" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target"><span>Français</span></a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Cloroprocain%C4%83" title="Cloroprocaină – Romanian" lang="ro" hreflang="ro" data-title="Cloroprocaină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target"><span>Română</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Hloroprokain" title="Hloroprokain – Serbian" lang="sr" hreflang="sr" data-title="Hloroprokain" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Hloroprokain" title="Hloroprokain – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Hloroprokain" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%A5%D0%BB%D0%BE%D1%80%D0%BE%D0%BF%D1%80%D0%BE%D0%BA%D0%B0%D1%97%D0%BD" title="Хлоропрокаїн – Ukrainian" lang="uk" hreflang="uk" data-title="Хлоропрокаїн" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target"><span>Українська</span></a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Chloroprocaine" title="Chloroprocaine – Vietnamese" lang="vi" hreflang="vi" data-title="Chloroprocaine" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target"><span>Tiếng Việt</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit wb-langlinks-link"><a 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noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent}.mw-parser-output .infobox-3cols-child{margin:auto}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme) div:not(.notheme){background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table tr{display:table-row!important}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Chloroprocaine">Chloroprocaine</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="skin-invert-image" typeof="mw:File"><a href="/wiki/File:Chloroprocaine.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Chloroprocaine.svg/250px-Chloroprocaine.svg.png" decoding="async" width="250" height="108" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/11/Chloroprocaine.svg/375px-Chloroprocaine.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/11/Chloroprocaine.svg/500px-Chloroprocaine.svg.png 2x" data-file-width="512" data-file-height="222" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Nesacaine, others</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/American_Society_of_Health-System_Pharmacists" title="American Society of Health-System Pharmacists">AHFS</a>/<a href="/wiki/Drugs.com" title="Drugs.com">Drugs.com</a></th><td class="infobox-data"><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li>Hcl: <span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/chloroprocaine-hydrochloride.html">Monograph</a></span></li><li>Ophthalmic: <span title="www.drugs.com"><a rel="nofollow" class="external text" href="https://www.drugs.com/mtm/chloroprocaine-ophthalmic.html">Multum Consumer Information</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">License data</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="United States">US</abbr></small> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <span title="dailymed.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Chloroprocaine">Chloroprocaine</a></span></li></ul></div> </td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></th><td class="infobox-data"><a href="/wiki/Intrathecal" class="mw-redirect" title="Intrathecal">Intrathecal</a>, <a href="/wiki/Ophthalmic_drug_administration" title="Ophthalmic drug administration">eye drop</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_class" title="Drug class">Drug class</a></th><td class="infobox-data"><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetic</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Anatomical_Therapeutic_Chemical_Classification_System" title="Anatomical Therapeutic Chemical Classification System">ATC code</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a href="/wiki/ATC_code_N01" title="ATC code N01">N01BA04</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=N01BA04">WHO</a></span>) <a href="/wiki/ATC_code_S01" title="ATC code S01">S01HA08</a> (<span title="www.whocc.no"><a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=S01HA08">WHO</a></span>)</li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"> <ul><li><small><abbr class="country-name" title="Canada">CA</abbr></small>: <a href="/wiki/Prescription_drug" title="Prescription drug"> ℞-only</a><sup id="cite_ref-Clorotekal_CA_RDS_1-0" class="reference"><a href="#cite_note-Clorotekal_CA_RDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup></li> <li><small><abbr class="country-name" title="United States">US</abbr>:</small> <a href="/wiki/Prescription_drug" title="Prescription drug">℞-only</a><sup id="cite_ref-Nesacaine_FDA_label_2-0" class="reference"><a href="#cite_note-Nesacaine_FDA_label-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Iheezo_FDA_label_3-0" class="reference"><a href="#cite_note-Iheezo_FDA_label-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Clorotekal_FDA_label_4-0" class="reference"><a href="#cite_note-Clorotekal_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></li> <li>Rx-only<sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;">2-diethylaminoethyl-4-amino-2-chloro-benzoate</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=133-16-4">133-16-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=3858-89-7">3858-89-7</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/8612">8612</a></span></li><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/441348">441348</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Guide_to_Pharmacology" title="Guide to Pharmacology">IUPHAR/BPS</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.guidetopharmacology.org"><a rel="nofollow" class="external text" href="https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7145">7145</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/DrugBank" title="DrugBank">DrugBank</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB01161">DB01161</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.drugbank.ca"><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DBSALT000823">DBSALT000823</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.8293.html">8293</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/5YVB0POT2H">5YVB0POT2H</a></span></li><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/LT7Z1YW11H">LT7Z1YW11H</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D07678">D07678</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00732">D00732</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3636">CHEBI:3636</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3637">CHEBI:3637</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1179047">ChEMBL1179047</a></span><sup> <span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup></li><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL944">ChEMBL944</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID8022799">DTXSID8022799</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2964133#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>13</sub><span title="Hydrogen">H</span><sub>19</sub><span title="Chlorine">Cl</span><span title="Nitrogen">N</span><sub>2</sub><span title="Oxygen">O</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002270760000000000♠"></span>270.76</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CCN%28CC%29CCOC%28%3DO%29C1%3DC%28Cl%29C%3DC%28N%29C%3DC1">Interactive image</a></span></li><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=Cl.CCN%28CC%29CCOC%28%3DO%29C1%3DC%28Cl%29C%3DC%28N%29C%3DC1">Interactive image</a></span></li></ul></div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1</div></li><li style="line-height: inherit; margin: 0"><br /><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Cl.CCN(CC)CCOC(=O)C1=C(Cl)C=C(N)C=C1</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H19ClN2O2/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14/h5-6,9H,3-4,7-8,15H2,1-2H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:VDANGULDQQJODZ-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></li><li style="line-height: inherit; margin: 0"><br /><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H19ClN2O2.ClH/c1-3-16(4-2)7-8-18-13(17)11-6-5-10(15)9-12(11)14;/h5-6,9H,3-4,7-8,15H2,1-2H3;1H</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:SZKQYDBPUCZLRX-UHFFFAOYSA-N</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-below"><style data-mw-deduplicate="TemplateStyles:r886047488">.mw-parser-output .nobold{font-weight:normal}</style><span class="nobold"> <sup><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup> <a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">(what is this?)</a></span><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r886047488"><span class="nobold">  <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=460032727&page2=Chloroprocaine">(verify)</a></span></span></td></tr></tbody></table> <p><b>Chloroprocaine</b>, sold under the brand name <b>Nesacaine</b> among others is a <a href="/wiki/Local_anesthetic" title="Local anesthetic">local anesthetic</a> given by <a href="/wiki/Injection_(medicine)" title="Injection (medicine)">injection</a>.<sup id="cite_ref-Nesacaine_FDA_label_2-1" class="reference"><a href="#cite_note-Nesacaine_FDA_label-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> It is used as the hydrochloride salt.<sup id="cite_ref-Clorotekal_FDA_label_4-1" class="reference"><a href="#cite_note-Clorotekal_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Chloroprocaine is a local anesthetic.<sup id="cite_ref-Nesacaine_FDA_label_2-2" class="reference"><a href="#cite_note-Nesacaine_FDA_label-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Clorotekal_FDA_label_4-2" class="reference"><a href="#cite_note-Clorotekal_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroprocaine&action=edit&section=1" title="Edit section: Medical uses"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroprocaine (Nesacaine) is <a href="/wiki/Indicated" class="mw-redirect" title="Indicated">indicated</a> for the production of local anesthesia by infiltration and peripheral nerve block;<sup id="cite_ref-Nesacaine_FDA_label_2-3" class="reference"><a href="#cite_note-Nesacaine_FDA_label-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and for the production of local anesthesia by infiltration, peripheral and central nerve block, including lumbar and caudal epidural blocks.<sup id="cite_ref-Nesacaine_FDA_label_2-4" class="reference"><a href="#cite_note-Nesacaine_FDA_label-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p><p>Chloroprocaine (Clorotekal) is indicated for intrathecal injection in adults for the production of subarachnoid block (spinal anesthesia).<sup id="cite_ref-Clorotekal_FDA_label_4-3" class="reference"><a href="#cite_note-Clorotekal_FDA_label-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>Chloroprocaine is used for <a href="/wiki/Regional_anesthesia" class="mw-redirect" title="Regional anesthesia">regional anesthesia</a> including <a href="/wiki/Spinal_anesthesia" class="mw-redirect" title="Spinal anesthesia">spinal anesthesia</a>, <a href="/wiki/Caudal_(anatomical_term)" class="mw-redirect" title="Caudal (anatomical term)">caudal</a> anesthesia and <a href="/wiki/Epidural_anesthesia" class="mw-redirect" title="Epidural anesthesia">epidural anesthesia</a>.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-PDR_7-0" class="reference"><a href="#cite_note-PDR-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>It is also indicated for <a href="/wiki/Local_anesthesia" title="Local anesthesia">local anesthesia</a> including <a href="/wiki/Brachial_plexus_block" title="Brachial plexus block">brachial plexus block</a>, <a href="/wiki/Cervical_nerve" class="mw-redirect" title="Cervical nerve">cervical nerve</a> block, <a href="/wiki/Occipital_nerve_block" title="Occipital nerve block">occipital nerve block</a>. <a href="/wiki/Mandibular_nerve" title="Mandibular nerve">mandibular nerve</a> block or <a href="/wiki/Maxillary_nerve" title="Maxillary nerve">maxillary nerve</a> block for <a href="/wiki/Dental_anesthesia" title="Dental anesthesia">dental anesthesia</a>, <a href="/wiki/Ophthalmology" title="Ophthalmology">ophthalmic</a> anesthesia via <a href="/wiki/Infraorbital_nerve" title="Infraorbital nerve">infraorbital nerve</a> block, <a href="/wiki/Ulnar_nerve" title="Ulnar nerve">ulnar nerve</a> block, <a href="/w/index.php?title=Paravertebral&action=edit&redlink=1" class="new" title="Paravertebral (page does not exist)">paravertebral</a> block, <a href="/wiki/Intercostal_nerve_block" title="Intercostal nerve block">intercostal nerve block</a>, <a href="/wiki/Sciatic_nerve_block" title="Sciatic nerve block">sciatic nerve block</a>, <a href="/wiki/Stellate_ganglion" title="Stellate ganglion">stellate ganglion</a> block, <a href="/wiki/Lumbar" title="Lumbar">lumbar</a> sympathetic block and <a href="/w/index.php?title=Interdigital&action=edit&redlink=1" class="new" title="Interdigital (page does not exist)">interdigital</a> block.<sup id="cite_ref-PDR_7-1" class="reference"><a href="#cite_note-PDR-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>It is also used for <a href="/wiki/Obstetric_anesthesia" class="mw-redirect" title="Obstetric anesthesia">obstetric anesthesia</a> including <a href="/wiki/Pudendal_nerve_block" class="mw-redirect" title="Pudendal nerve block">pudendal nerve block</a> and <a href="/wiki/Paracervical_block" title="Paracervical block">paracervical block</a>.<sup id="cite_ref-PDR_7-2" class="reference"><a href="#cite_note-PDR-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>Chloroprocaine (Iheezo) is indicated for ocular surface anesthesia.<sup id="cite_ref-Iheezo_FDA_label_3-1" class="reference"><a href="#cite_note-Iheezo_FDA_label-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Subarachnoid_block">Subarachnoid block</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroprocaine&action=edit&section=2" title="Edit section: Subarachnoid block"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Chloroprocaine was developed to meet the need for a short-acting spinal anaesthetic that is reliable and has a favourable safety profile to support the growing need for day-case surgery. Licensed in Europe for surgical procedures up to 40 minutes, chloroprocaine is an ester-type local anaesthetic with the shortest duration of action of all the established local anaesthetics. It has a significantly shorter duration of action than lidocaine and is significantly less toxic. Chloroprocaine has a motor block lasting for 40 minutes, a rapid onset time of 3–5 minutes (9.6 min ± 7.3 min at 40 mg dose; 7.9 min ± 6.0 min at 50 mg dose) and a time to ambulation of 90 minutes without complications, especially lacking transient neurologic symptomatology. </p><p>These data are based upon a retrospective review of 672 patients suitable for spinal anesthesia in surgical procedures less than 60 minutes' duration using 30–40 mg chloroprocaine. The results showed good surgical anesthesia, a fast onset time, and postoperative mobilization after 90 minutes without complications.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> </p><p>The use of chloroprocaine in the <a href="/wiki/Subarachnoid" class="mw-redirect" title="Subarachnoid">subarachnoid</a> space has been questioned.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In the early 1980s, several cases were reported of neurological deficits after inadvertent intrathecal injections intended for epidural delivery.<sup id="cite_ref-pmid7189987_10-0" class="reference"><a href="#cite_note-pmid7189987-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> These doses were an order of magnitude higher than is currently used for intrathecal delivery.<sup id="cite_ref-pmid21039353_11-0" class="reference"><a href="#cite_note-pmid21039353-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Förster_2013_12-0" class="reference"><a href="#cite_note-Förster_2013-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid21203878_13-0" class="reference"><a href="#cite_note-pmid21203878-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> It is also thought that these deficits were also related to the preservative <a href="/wiki/Sodium_bisulfite" title="Sodium bisulfite">sodium bisulfite</a>,<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid1443708_15-0" class="reference"><a href="#cite_note-pmid1443708-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> although this is also controversial.<sup id="cite_ref-pmid14695728_16-0" class="reference"><a href="#cite_note-pmid14695728-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-pmid2346671_17-0" class="reference"><a href="#cite_note-pmid2346671-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> </p><p>Some studies have been published on the safe use of intrathecal chloroprocaine when appropriate dosage is used and with preservative-free preparations.<sup id="cite_ref-pmid23320599_18-0" class="reference"><a href="#cite_note-pmid23320599-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Förster_2013_12-1" class="reference"><a href="#cite_note-Förster_2013-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> </p><p>It is approved for intrathecal use in the United States,<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> Europe,<sup id="cite_ref-20" class="reference"><a href="#cite_note-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> and Canada.<sup id="cite_ref-Clorotekal_CA_RDS_1-1" class="reference"><a href="#cite_note-Clorotekal_CA_RDS-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Obstetrics">Obstetrics</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroprocaine&action=edit&section=3" title="Edit section: Obstetrics"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Amide-linked local anesthetic agents, such as <a href="/wiki/Lidocaine" title="Lidocaine">lidocaine</a> and <a href="/wiki/Bupivacaine" title="Bupivacaine">bupivacaine</a>, can become "trapped" in their ionized forms on the fetal side of the <a href="/wiki/Placenta" title="Placenta">placenta</a>, so their net transfer across the placenta is increased. An ester-linked local anesthetic agent, such as 2-chloroprocaine, is rapidly metabolized, and placental transfer is limited. Since the metabolism of 2-chloroprocaine by fetal plasma is slower than in maternal plasma, the potential for ion trapping exists. Fetal pH is slightly lower than maternal (7.32 to 7.38), thus most unionized drugs are "ion trapped" to a degree, even in a healthy fetus. Chloroprocaine (pKa 8.7) is the drug of choice for <a href="/wiki/Epidural" class="mw-redirect" title="Epidural">epidural</a> analgesia and a decompensating fetus, because it does not participate in ion trapping. Placental transfer of 2-chloroprocaine is not influenced by fetal acidosis.<sup id="cite_ref-pmid3970100_21-0" class="reference"><a href="#cite_note-pmid3970100-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> </p><p>The <i>in vitro</i> <a href="/wiki/Half-life" title="Half-life">half-life</a> of chloroprocaine is 21 seconds for maternal and 43 seconds for fetal blood. In patients who are homozygous atypical for plasma cholinesterase, chloroprocaine typically exists for two minutes in circulation.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroprocaine&action=edit&section=4" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1251242444">.mw-parser-output .ambox{border:1px solid #a2a9b1;border-left:10px solid #36c;background-color:#fbfbfb;box-sizing:border-box}.mw-parser-output .ambox+link+.ambox,.mw-parser-output .ambox+link+style+.ambox,.mw-parser-output .ambox+link+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+style+.ambox,.mw-parser-output .ambox+.mw-empty-elt+link+link+.ambox{margin-top:-1px}html body.mediawiki .mw-parser-output .ambox.mbox-small-left{margin:4px 1em 4px 0;overflow:hidden;width:238px;border-collapse:collapse;font-size:88%;line-height:1.25em}.mw-parser-output .ambox-speedy{border-left:10px solid #b32424;background-color:#fee7e6}.mw-parser-output .ambox-delete{border-left:10px solid #b32424}.mw-parser-output .ambox-content{border-left:10px solid #f28500}.mw-parser-output .ambox-style{border-left:10px solid #fc3}.mw-parser-output .ambox-move{border-left:10px solid #9932cc}.mw-parser-output .ambox-protection{border-left:10px solid #a2a9b1}.mw-parser-output .ambox .mbox-text{border:none;padding:0.25em 0.5em;width:100%}.mw-parser-output .ambox .mbox-image{border:none;padding:2px 0 2px 0.5em;text-align:center}.mw-parser-output .ambox .mbox-imageright{border:none;padding:2px 0.5em 2px 0;text-align:center}.mw-parser-output .ambox .mbox-empty-cell{border:none;padding:0;width:1px}.mw-parser-output .ambox .mbox-image-div{width:52px}@media(min-width:720px){.mw-parser-output .ambox{margin:0 10%}}@media print{body.ns-0 .mw-parser-output .ambox{display:none!important}}</style><table class="box-Unreferenced_section plainlinks metadata ambox ambox-content ambox-Unreferenced" role="presentation"><tbody><tr><td class="mbox-image"><div class="mbox-image-div"><span typeof="mw:File"><a href="/wiki/File:Question_book-new.svg" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/50px-Question_book-new.svg.png" decoding="async" width="50" height="39" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/75px-Question_book-new.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/99/Question_book-new.svg/100px-Question_book-new.svg.png 2x" data-file-width="512" data-file-height="399" /></a></span></div></td><td class="mbox-text"><div class="mbox-text-span">This section <b>does not <a href="/wiki/Wikipedia:Citing_sources" title="Wikipedia:Citing sources">cite</a> any <a href="/wiki/Wikipedia:Verifiability" title="Wikipedia:Verifiability">sources</a></b>.<span class="hide-when-compact"> Please help <a href="/wiki/Special:EditPage/Chloroprocaine" title="Special:EditPage/Chloroprocaine">improve this section</a> by <a href="/wiki/Help:Referencing_for_beginners" title="Help:Referencing for beginners">adding citations to reliable sources</a>. Unsourced material may be challenged and <a href="/wiki/Wikipedia:Verifiability#Burden_of_evidence" title="Wikipedia:Verifiability">removed</a>.</span> <span class="date-container"><i>(<span class="date">September 2022</span>)</i></span><span class="hide-when-compact"><i> (<small><a href="/wiki/Help:Maintenance_template_removal" title="Help:Maintenance template removal">Learn how and when to remove this message</a></small>)</i></span></div></td></tr></tbody></table> <figure class="mw-halign-center skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Chloroprocaine_synthesis.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Chloroprocaine_synthesis.png/800px-Chloroprocaine_synthesis.png" decoding="async" width="800" height="103" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/33/Chloroprocaine_synthesis.png/1200px-Chloroprocaine_synthesis.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/33/Chloroprocaine_synthesis.png/1600px-Chloroprocaine_synthesis.png 2x" data-file-width="1900" data-file-height="245" /></a><figcaption>Chloroprocaine synthesis: H.C. Marks, H.I. Rubin, <span><a rel="nofollow" class="external text" href="https://patents.google.com/patent/US2460139">U.S. patent 2,460,139</a></span> (1949 to Wallace & Tiernan Inc).</figcaption></figure> <p>The hydrochloride salt of 4-amino-2-chlorobenzoyl chloride is made by the reaction of 2-chloro-4-aminobenzoic acid with thionyl chloride.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> Synthesis of this drug is then accomplished by directly reacting the product of the last step with the hydrochloride salt of <a href="/wiki/2-diethylaminoethanol" class="mw-redirect" title="2-diethylaminoethanol">2-diethylaminoethanol</a>. </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Chloroprocaine&action=edit&section=5" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-Clorotekal_CA_RDS-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-Clorotekal_CA_RDS_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-Clorotekal_CA_RDS_1-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS1733408271619">"Regulatory Decision Summary for Clorotekal"</a>. <i>Drug and Health Products Portal</i>. 22 August 2024<span class="reference-accessdate">. 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Philadelphia: Lippincott Williams & Wilkins. p. 75. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-683-30665-1" title="Special:BookSources/978-0-683-30665-1"><bdi>978-0-683-30665-1</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Shnider+and+Levinson%27s+Anesthesia+for+Obstetrics&rft.place=Philadelphia&rft.pages=75&rft.edition=4th&rft.pub=Lippincott+Williams+%26+Wilkins&rft.date=2002&rft.isbn=978-0-683-30665-1&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroprocaine" class="Z3988"></span></span> </li> <li id="cite_note-24"><span class="mw-cite-backlink"><b><a href="#cite_ref-24">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFVardanyanHruby2006" class="citation book cs1">Vardanyan RS, Hruby VJ (January 2006). "Local anesthetics". <i>Synthesis of Essential Drugs</i>. Amsterdam: Elsevier. pp. <span class="nowrap">9–</span>18. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fb978-044452166-8%2F50002-9">10.1016/b978-044452166-8/50002-9</a>. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-444-52166-8" title="Special:BookSources/978-0-444-52166-8"><bdi>978-0-444-52166-8</bdi></a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=bookitem&rft.atitle=Local+anesthetics&rft.btitle=Synthesis+of+Essential+Drugs&rft.place=Amsterdam&rft.pages=%3Cspan+class%3D%22nowrap%22%3E9-%3C%2Fspan%3E18&rft.pub=Elsevier&rft.date=2006-01&rft_id=info%3Adoi%2F10.1016%2Fb978-044452166-8%2F50002-9&rft.isbn=978-0-444-52166-8&rft.aulast=Vardanyan&rft.aufirst=RS&rft.au=Hruby%2C+VJ&rfr_id=info%3Asid%2Fen.wikipedia.org%3AChloroprocaine" class="Z3988"></span></span> </li> </ol></div></div> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist dl,.mw-parser-output .hlist ol,.mw-parser-output .hlist ul{margin:0;padding:0}.mw-parser-output .hlist dd,.mw-parser-output .hlist dt,.mw-parser-output .hlist li{margin:0;display:inline}.mw-parser-output .hlist.inline,.mw-parser-output .hlist.inline dl,.mw-parser-output .hlist.inline ol,.mw-parser-output .hlist.inline ul,.mw-parser-output .hlist dl dl,.mw-parser-output .hlist dl ol,.mw-parser-output .hlist dl ul,.mw-parser-output .hlist ol dl,.mw-parser-output .hlist ol ol,.mw-parser-output .hlist ol ul,.mw-parser-output .hlist ul dl,.mw-parser-output .hlist ul ol,.mw-parser-output .hlist ul ul{display:inline}.mw-parser-output .hlist .mw-empty-li{display:none}.mw-parser-output .hlist dt::after{content:": "}.mw-parser-output .hlist dd::after,.mw-parser-output .hlist li::after{content:" · ";font-weight:bold}.mw-parser-output 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.navbox-even{background-color:#f7f7f7}.mw-parser-output .navbox-odd{background-color:transparent}.mw-parser-output .navbox .hlist td dl,.mw-parser-output .navbox .hlist td ol,.mw-parser-output .navbox .hlist td ul,.mw-parser-output .navbox td.hlist dl,.mw-parser-output .navbox td.hlist ol,.mw-parser-output .navbox td.hlist ul{padding:0.125em 0}.mw-parser-output .navbox .navbar{display:block;font-size:100%}.mw-parser-output .navbox-title .navbar{float:left;text-align:left;margin-right:0.5em}body.skin--responsive .mw-parser-output .navbox-image img{max-width:none!important}@media print{body.ns-0 .mw-parser-output .navbox{display:none!important}}</style><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"></div><div role="navigation" class="navbox" aria-labelledby="Local_anesthetics_(primarily_sodium_channel_blockers)_(N01B)490" style="padding:3px"><table class="nowraplinks mw-collapsible autocollapse navbox-inner" style="border-spacing:0;background:transparent;color:inherit"><tbody><tr><th scope="col" class="navbox-title" colspan="2"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><style data-mw-deduplicate="TemplateStyles:r1239400231">.mw-parser-output .navbar{display:inline;font-size:88%;font-weight:normal}.mw-parser-output .navbar-collapse{float:left;text-align:left}.mw-parser-output .navbar-boxtext{word-spacing:0}.mw-parser-output .navbar ul{display:inline-block;white-space:nowrap;line-height:inherit}.mw-parser-output .navbar-brackets::before{margin-right:-0.125em;content:"[ "}.mw-parser-output .navbar-brackets::after{margin-left:-0.125em;content:" ]"}.mw-parser-output .navbar li{word-spacing:-0.125em}.mw-parser-output .navbar a>span,.mw-parser-output .navbar a>abbr{text-decoration:inherit}.mw-parser-output .navbar-mini abbr{font-variant:small-caps;border-bottom:none;text-decoration:none;cursor:inherit}.mw-parser-output .navbar-ct-full{font-size:114%;margin:0 7em}.mw-parser-output .navbar-ct-mini{font-size:114%;margin:0 4em}html.skin-theme-clientpref-night .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}@media(prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .navbar li a abbr{color:var(--color-base)!important}}@media print{.mw-parser-output .navbar{display:none!important}}</style><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Local_anesthetics" title="Template:Local anesthetics"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Local_anesthetics" title="Template talk:Local anesthetics"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Local_anesthetics" title="Special:EditPage/Template:Local anesthetics"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Local_anesthetics_(primarily_sodium_channel_blockers)_(N01B)490" style="font-size:114%;margin:0 4em"><a href="/wiki/Local_anesthetic" title="Local anesthetic">Local anesthetics</a> <span style="font-size:85%;">(primarily <a href="/wiki/Sodium_channel_blocker" title="Sodium channel blocker">sodium channel blockers</a>)</span> (<a href="/wiki/ATC_code_N01#N01B" title="ATC code N01">N01B</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Ester" title="Ester">Esters</a> by acid</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/4-Aminobenzoic_acid" title="4-Aminobenzoic acid">Aminobenzoic</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Benzocaine" title="Benzocaine">Benzocaine</a></li> <li><a href="/wiki/Benzonatate" title="Benzonatate">Benzonatate</a></li> <li><a href="/wiki/Butacaine" title="Butacaine">Butacaine</a></li> <li><a href="/wiki/Butamben" title="Butamben">Butamben</a></li> <li><a class="mw-selflink selflink">Chloroprocaine</a></li> <li><a href="/wiki/Dimethocaine" title="Dimethocaine">Dimethocaine</a></li> <li><a href="/wiki/Lucaine" class="mw-redirect" title="Lucaine">Lucaine</a></li> <li><a href="/wiki/Meprylcaine" title="Meprylcaine">Meprylcaine</a></li> <li><a href="/wiki/Metabutethamine" title="Metabutethamine">Metabutethamine</a></li> <li><a href="/wiki/Metabutoxycaine" title="Metabutoxycaine">Metabutoxycaine</a></li> <li><a href="/wiki/Nitracaine" title="Nitracaine">Nitracaine</a></li> <li><a href="/wiki/Orthocaine" title="Orthocaine">Orthocaine</a></li> <li><a href="/wiki/Propoxycaine" title="Propoxycaine">Propoxycaine</a></li> <li><a href="/wiki/Procaine" title="Procaine">Procaine (Novocaine)</a></li> <li><a href="/wiki/Proxymetacaine" title="Proxymetacaine">Proxymetacaine</a></li> <li><a href="/wiki/Risocaine" title="Risocaine">Risocaine</a></li> <li><a href="/wiki/Tetracaine" title="Tetracaine">Tetracaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Benzoic_acid" title="Benzoic acid">Benzoic</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Amylocaine" title="Amylocaine">Amylocaine</a></li> <li><a href="/wiki/Cocaine" title="Cocaine">Cocaine</a></li> <li><a href="/wiki/Cyclomethycaine" title="Cyclomethycaine">Cyclomethycaine</a></li> <li><a href="/wiki/Alpha-Eucaine" class="mw-redirect" title="Alpha-Eucaine">α-Eucaine</a></li> <li><a href="/wiki/Eucaine" title="Eucaine">β-Eucaine</a></li> <li><a href="/wiki/Hexylcaine" title="Hexylcaine">Hexylcaine</a></li> <li><a href="/wiki/Isobucaine" title="Isobucaine">Isobucaine</a></li> <li><a href="/wiki/Piperocaine" title="Piperocaine">Piperocaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">ArCO2- (not para-amino or Ph)</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/w/index.php?title=Amoproxan&action=edit&redlink=1" class="new" title="Amoproxan (page does not exist)">Amoproxan</a> (3,4,5-Trimethoxybenzoyl)</li> <li><a href="/wiki/3-(p-Fluorobenzoyloxy)tropane" title="3-(p-Fluorobenzoyloxy)tropane">3-(p-Fluorobenzoyloxy)tropane</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Amide" title="Amide">Amides</a></th><td class="navbox-list-with-group navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Articaine" title="Articaine">Articaine</a></li> <li><a href="/wiki/Bupivacaine" title="Bupivacaine">Bupivacaine</a><sup>#</sup>/<a href="/wiki/Levobupivacaine" title="Levobupivacaine">Levobupivacaine</a>/<a href="/wiki/Ropivacaine" title="Ropivacaine">Ropivacaine</a></li> <li><a href="/wiki/Butanilicaine" title="Butanilicaine">Butanilicaine</a></li> <li><a href="/wiki/Articaine" title="Articaine">Carticaine</a></li> <li><a href="/wiki/Cinchocaine" title="Cinchocaine"> Cinchocaine (Dibucaine)</a></li> <li><a href="/wiki/Etidocaine" title="Etidocaine">Etidocaine</a></li> <li><a href="/wiki/Lidocaine" title="Lidocaine">Lidocaine</a><sup>#</sup></li> <li><a href="/wiki/Mepivacaine" title="Mepivacaine">Mepivacaine</a></li> <li><a href="/wiki/Prilocaine" title="Prilocaine">Prilocaine</a></li> <li><a href="/wiki/Trimecaine" title="Trimecaine">Trimecaine</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Combinations</th><td class="navbox-list-with-group navbox-list navbox-odd hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Local_anesthetic_with_vasoconstrictor" class="mw-redirect" title="Local anesthetic with vasoconstrictor">Anesthetic/vasoconstrictor</a></li> <li><a href="/wiki/Bupivacaine/meloxicam" title="Bupivacaine/meloxicam">Bupivacaine/meloxicam</a></li> <li><a href="/wiki/Lidocaine/prilocaine" title="Lidocaine/prilocaine">Lidocaine/prilocaine</a></li> <li><a href="/wiki/Topical_tac" title="Topical tac">TAC</a></li> <li><a href="/wiki/Iontocaine" title="Iontocaine">Iontocaine</a></li></ul> </div></td></tr><tr><td class="navbox-abovebelow" colspan="2" style="padding:0;"><div><div class="hlist"> <ul><li><sup>#</sup><a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li><sup>‡</sup><a href="/wiki/List_of_withdrawn_drugs" title="List of withdrawn drugs">Withdrawn</a> from market</li> <li><a href="/wiki/Clinical_trial" title="Clinical trial">Clinical trials</a>: <ul><li><sup>†</sup><a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li><sup>§</sup>Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <style data-mw-deduplicate="TemplateStyles:r1130092004">.mw-parser-output .portal-bar{font-size:88%;font-weight:bold;display:flex;justify-content:center;align-items:baseline}.mw-parser-output .portal-bar-bordered{padding:0 2em;background-color:#fdfdfd;border:1px solid #a2a9b1;clear:both;margin:1em auto 0}.mw-parser-output .portal-bar-related{font-size:100%;justify-content:flex-start}.mw-parser-output .portal-bar-unbordered{padding:0 1.7em;margin-left:0}.mw-parser-output .portal-bar-header{margin:0 1em 0 0.5em;flex:0 0 auto;min-height:24px}.mw-parser-output .portal-bar-content{display:flex;flex-flow:row wrap;flex:0 1 auto;padding:0.15em 0;column-gap:1em;align-items:baseline;margin:0;list-style:none}.mw-parser-output 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.sister-bar+style+.portal-bar,.mw-parser-output .portal-bar+.navbox-styles+.navbox,.mw-parser-output .portal-bar+.navbox-styles+.sister-bar{margin-top:-1px}</style><div class="portal-bar noprint metadata noviewer portal-bar-bordered" role="navigation" aria-label="Portals"><span class="portal-bar-header"><a href="/wiki/Wikipedia:Contents/Portals" title="Wikipedia:Contents/Portals">Portal</a>:</span><ul class="portal-bar-content"><li class="portal-bar-item"><span class="nowrap"><span typeof="mw:File"><span><img alt="icon" src="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/8px-WHO_Rod.svg.png" decoding="async" width="8" height="19" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/12px-WHO_Rod.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/d/d6/WHO_Rod.svg/16px-WHO_Rod.svg.png 2x" data-file-width="107" data-file-height="250" /></span></span> </span><a href="/wiki/Portal:Medicine" title="Portal:Medicine">Medicine</a></li></ul></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Chloroprocaine&oldid=1273236412">https://en.wikipedia.org/w/index.php?title=Chloroprocaine&oldid=1273236412</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Local_anesthetics" title="Category:Local anesthetics">Local anesthetics</a></li><li><a href="/wiki/Category:4-Aminobenzoate_esters" title="Category:4-Aminobenzoate esters">4-Aminobenzoate esters</a></li><li><a href="/wiki/Category:Chlorobenzene_derivatives" 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