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class="vector-toc-link" href="#Medical_uses"> <div class="vector-toc-text"> 3 Medical uses </div> </a> <button aria-controls="toc-Medical_uses-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Medical uses subsection </button> <ul id="toc-Medical_uses-sublist" class="vector-toc-list"> <li id="toc-Treatment_of_deficiency" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Treatment_of_deficiency"> <div class="vector-toc-text"> 3.1 Treatment of deficiency </div> </a> <ul id="toc-Treatment_of_deficiency-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cyanide_poisoning" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cyanide_poisoning"> <div class="vector-toc-text"> 3.2 Cyanide poisoning </div> </a> <ul id="toc-Cyanide_poisoning-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Dietary_recommendations" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Dietary_recommendations"> <div class="vector-toc-text"> 4 Dietary recommendations </div> </a> <ul id="toc-Dietary_recommendations-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Sources" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Sources"> <div class="vector-toc-text"> 5 Sources </div> </a> <button aria-controls="toc-Sources-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Sources subsection </button> <ul id="toc-Sources-sublist" class="vector-toc-list"> <li id="toc-Bacteria_and_archaea" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Bacteria_and_archaea"> <div class="vector-toc-text"> 5.1 Bacteria and archaea </div> </a> <ul id="toc-Bacteria_and_archaea-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Animal-derived_foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Animal-derived_foods"> <div class="vector-toc-text"> 5.2 Animal-derived foods </div> </a> <ul id="toc-Animal-derived_foods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Plants_and_algae" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Plants_and_algae"> <div class="vector-toc-text"> 5.3 Plants and algae </div> </a> <ul id="toc-Plants_and_algae-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Fortified_foods" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Fortified_foods"> <div class="vector-toc-text"> 5.4 Fortified foods </div> </a> <ul id="toc-Fortified_foods-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Supplements" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Supplements"> <div class="vector-toc-text"> 5.5 Supplements </div> </a> <ul id="toc-Supplements-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Intramuscular_or_intravenous_injection" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Intramuscular_or_intravenous_injection"> <div class="vector-toc-text"> 5.6 Intramuscular or intravenous injection </div> </a> <ul id="toc-Intramuscular_or_intravenous_injection-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Nanotechnologies_used_in_vitamin_B12_supplementation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Nanotechnologies_used_in_vitamin_B12_supplementation"> <div class="vector-toc-text"> 5.7 Nanotechnologies used in vitamin B12 supplementation </div> </a> <ul id="toc-Nanotechnologies_used_in_vitamin_B12_supplementation-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Pseudovitamin-B12" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Pseudovitamin-B12"> <div class="vector-toc-text"> 5.8 Pseudovitamin-B12 </div> </a> <ul id="toc-Pseudovitamin-B12-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Drug_interactions" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Drug_interactions"> <div class="vector-toc-text"> 6 Drug interactions </div> </a> <button aria-controls="toc-Drug_interactions-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Drug interactions subsection </button> <ul id="toc-Drug_interactions-sublist" class="vector-toc-list"> <li id="toc-H2-receptor_antagonists_and_proton-pump_inhibitors" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#H2-receptor_antagonists_and_proton-pump_inhibitors"> <div class="vector-toc-text"> 6.1 H2-receptor antagonists and proton-pump inhibitors </div> </a> <ul id="toc-H2-receptor_antagonists_and_proton-pump_inhibitors-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metformin" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metformin"> <div class="vector-toc-text"> 6.2 Metformin </div> </a> <ul id="toc-Metformin-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Other_drugs" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Other_drugs"> <div class="vector-toc-text"> 6.3 Other drugs </div> </a> <ul id="toc-Other_drugs-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Chemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Chemistry"> <div class="vector-toc-text"> 7 Chemistry </div> </a> <button aria-controls="toc-Chemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Chemistry subsection </button> <ul id="toc-Chemistry-sublist" class="vector-toc-list"> <li id="toc-Methods_for_the_analysis_of_vitamin_B12_in_food" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Methods_for_the_analysis_of_vitamin_B12_in_food"> <div class="vector-toc-text"> 7.1 Methods for the analysis of vitamin B12 in food </div> </a> <ul id="toc-Methods_for_the_analysis_of_vitamin_B12_in_food-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Biochemistry" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Biochemistry"> <div class="vector-toc-text"> 8 Biochemistry </div> </a> <button aria-controls="toc-Biochemistry-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Biochemistry subsection </button> <ul id="toc-Biochemistry-sublist" class="vector-toc-list"> <li id="toc-Coenzyme_function" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Coenzyme_function"> <div class="vector-toc-text"> 8.1 Coenzyme function </div> </a> <ul id="toc-Coenzyme_function-sublist" class="vector-toc-list"> <li id="toc-Methylmalonyl-CoA_mutase" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Methylmalonyl-CoA_mutase"> <div class="vector-toc-text"> 8.1.1 Methylmalonyl-CoA mutase </div> </a> <ul id="toc-Methylmalonyl-CoA_mutase-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Methionine_synthase" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Methionine_synthase"> <div class="vector-toc-text"> 8.1.2 Methionine synthase </div> </a> <ul id="toc-Methionine_synthase-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> </ul> </li> <li id="toc-Physiology" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Physiology"> <div class="vector-toc-text"> 9 Physiology </div> </a> <button aria-controls="toc-Physiology-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Physiology subsection </button> <ul id="toc-Physiology-sublist" class="vector-toc-list"> <li id="toc-Absorption" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Absorption"> <div class="vector-toc-text"> 9.1 Absorption </div> </a> <ul id="toc-Absorption-sublist" class="vector-toc-list"> <li id="toc-Malabsorption" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Malabsorption"> <div class="vector-toc-text"> 9.1.1 Malabsorption </div> </a> <ul id="toc-Malabsorption-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Storage_and_excretion" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Storage_and_excretion"> <div class="vector-toc-text"> 9.2 Storage and excretion </div> </a> <ul id="toc-Storage_and_excretion-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Cellular_reprogramming" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Cellular_reprogramming"> <div class="vector-toc-text"> 9.3 Cellular reprogramming </div> </a> <ul id="toc-Cellular_reprogramming-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> 10 Synthesis </div> </a> <button aria-controls="toc-Synthesis-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle Synthesis subsection </button> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> <li id="toc-Biosynthesis" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biosynthesis"> <div class="vector-toc-text"> 10.1 Biosynthesis </div> </a> <ul id="toc-Biosynthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Industrial" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Industrial"> <div class="vector-toc-text"> 10.2 Industrial </div> </a> <ul id="toc-Industrial-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Laboratory" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Laboratory"> <div class="vector-toc-text"> 10.3 Laboratory </div> </a> <ul id="toc-Laboratory-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-History" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#History"> <div class="vector-toc-text"> 11 History </div> </a> <button aria-controls="toc-History-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> Toggle History subsection </button> <ul id="toc-History-sublist" class="vector-toc-list"> <li id="toc-Descriptions_of_deficiency_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Descriptions_of_deficiency_effects"> <div class="vector-toc-text"> 11.1 Descriptions of deficiency effects </div> </a> <ul id="toc-Descriptions_of_deficiency_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Identification_of_liver_as_an_anti-anemia_food" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Identification_of_liver_as_an_anti-anemia_food"> <div class="vector-toc-text"> 11.2 Identification of liver as an anti-anemia food </div> </a> <ul id="toc-Identification_of_liver_as_an_anti-anemia_food-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Identification_of_the_active_compound" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Identification_of_the_active_compound"> <div class="vector-toc-text"> 11.3 Identification of the active compound </div> </a> <ul id="toc-Identification_of_the_active_compound-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Commercial_production" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Commercial_production"> <div class="vector-toc-text"> 11.4 Commercial production </div> </a> <ul id="toc-Commercial_production-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Society_and_culture" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Society_and_culture"> <div class="vector-toc-text"> 12 Society and culture </div> </a> <ul id="toc-Society_and_culture-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-See_also" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#See_also"> <div class="vector-toc-text"> 13 See also </div> </a> <ul id="toc-See_also-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Further_reading" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#Further_reading"> <div class="vector-toc-text"> 14 Further reading </div> </a> <ul id="toc-Further_reading-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-References" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#References"> <div class="vector-toc-text"> 15 References </div> </a> <ul id="toc-References-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-External_links" class="vector-toc-list-item vector-toc-level-1"> <a class="vector-toc-link" href="#External_links"> <div class="vector-toc-text"> 16 External links </div> </a> <ul id="toc-External_links-sublist" class="vector-toc-list"> </ul> </li> </ul> </div> </div> </nav> </div> </div> <div class="mw-content-container"> <main id="content" class="mw-body"> <header class="mw-body-header vector-page-titlebar"> <nav aria-label="Contents" class="vector-toc-landmark"> <div id="vector-page-titlebar-toc" class="vector-dropdown vector-page-titlebar-toc vector-button-flush-left" > <input type="checkbox" id="vector-page-titlebar-toc-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-vector-page-titlebar-toc" class="vector-dropdown-checkbox " aria-label="Toggle the table of contents" > <label id="vector-page-titlebar-toc-label" for="vector-page-titlebar-toc-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--icon-only " aria-hidden="true" > Toggle the table of contents </label> <div class="vector-dropdown-content"> <div id="vector-page-titlebar-toc-unpinned-container" class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading">Vitamin B12</h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. Available in 70 languages" > <label id="p-lang-btn-label" for="p-lang-btn-checkbox" class="vector-dropdown-label cdx-button cdx-button--fake-button cdx-button--fake-button--enabled cdx-button--weight-quiet cdx-button--action-progressive mw-portlet-lang-heading-70" aria-hidden="true" > 70 languages </label> <div class="vector-dropdown-content"> <div class="vector-menu-content"> <ul class="vector-menu-content-list"> <li class="interlanguage-link interwiki-af mw-list-item"><a href="https://af.wikipedia.org/wiki/Vitamien_B12" title="Vitamien B12 – Afrikaans" lang="af" hreflang="af" data-title="Vitamien B12" data-language-autonym="Afrikaans" data-language-local-name="Afrikaans" class="interlanguage-link-target">Afrikaans</a></li><li class="interlanguage-link interwiki-ar mw-list-item"><a href="https://ar.wikipedia.org/wiki/%D9%81%D9%8A%D8%AA%D8%A7%D9%85%D9%8A%D9%86_%D8%A8%D9%8A_12" title="فيتامين بي 12 – Arabic" lang="ar" hreflang="ar" data-title="فيتامين بي 12" data-language-autonym="العربية" data-language-local-name="Arabic" class="interlanguage-link-target">العربية</a></li><li class="interlanguage-link interwiki-az mw-list-item"><a href="https://az.wikipedia.org/wiki/B12_vitamini" title="B12 vitamini – Azerbaijani" lang="az" hreflang="az" data-title="B12 vitamini" data-language-autonym="Azərbaycanca" data-language-local-name="Azerbaijani" class="interlanguage-link-target">Azərbaycanca</a></li><li class="interlanguage-link interwiki-azb mw-list-item"><a href="https://azb.wikipedia.org/wiki/%D9%88%DB%8C%D8%AA%D8%A7%D9%85%DB%8C%D9%86_%D8%A8%DB%B1%DB%B2" title="ویتامین ب۱۲ – South Azerbaijani" lang="azb" hreflang="azb" data-title="ویتامین ب۱۲" data-language-autonym="تۆرکجه" data-language-local-name="South Azerbaijani" class="interlanguage-link-target">تۆرکجه</a></li><li class="interlanguage-link interwiki-bh mw-list-item"><a href="https://bh.wikipedia.org/wiki/%E0%A4%B5%E0%A4%BF%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8_%E0%A4%AC%E0%A5%8012" title="विटामिन बी12 – Bhojpuri" lang="bh" hreflang="bh" data-title="विटामिन बी12" data-language-autonym="भोजपुरी" data-language-local-name="Bhojpuri" class="interlanguage-link-target">भोजपुरी</a></li><li class="interlanguage-link interwiki-bcl mw-list-item"><a href="https://bcl.wikipedia.org/wiki/Bitamina_B12" title="Bitamina B12 – Central Bikol" lang="bcl" hreflang="bcl" data-title="Bitamina B12" data-language-autonym="Bikol Central" data-language-local-name="Central Bikol" class="interlanguage-link-target">Bikol Central</a></li><li class="interlanguage-link interwiki-bg mw-list-item"><a href="https://bg.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_B12" title="Витамин B12 – Bulgarian" lang="bg" hreflang="bg" data-title="Витамин B12" data-language-autonym="Български" data-language-local-name="Bulgarian" class="interlanguage-link-target">Български</a></li><li class="interlanguage-link interwiki-bs mw-list-item"><a href="https://bs.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Bosnian" lang="bs" hreflang="bs" data-title="Vitamin B12" data-language-autonym="Bosanski" data-language-local-name="Bosnian" class="interlanguage-link-target">Bosanski</a></li><li class="interlanguage-link interwiki-ca mw-list-item"><a href="https://ca.wikipedia.org/wiki/Vitamina_B%E2%82%81%E2%82%82" title="Vitamina B₁₂ – Catalan" lang="ca" hreflang="ca" data-title="Vitamina B₁₂" data-language-autonym="Català" data-language-local-name="Catalan" class="interlanguage-link-target">Català</a></li><li class="interlanguage-link interwiki-cs mw-list-item"><a href="https://cs.wikipedia.org/wiki/Vitam%C3%ADn_B12" title="Vitamín B12 – Czech" lang="cs" hreflang="cs" data-title="Vitamín B12" data-language-autonym="Čeština" data-language-local-name="Czech" class="interlanguage-link-target">Čeština</a></li><li class="interlanguage-link interwiki-cy mw-list-item"><a href="https://cy.wikipedia.org/wiki/Fitamin_B12" title="Fitamin B12 – Welsh" lang="cy" hreflang="cy" data-title="Fitamin B12" data-language-autonym="Cymraeg" data-language-local-name="Welsh" class="interlanguage-link-target">Cymraeg</a></li><li class="interlanguage-link interwiki-da mw-list-item"><a href="https://da.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Danish" lang="da" hreflang="da" data-title="Vitamin B12" data-language-autonym="Dansk" data-language-local-name="Danish" class="interlanguage-link-target">Dansk</a></li><li class="interlanguage-link interwiki-de mw-list-item"><a href="https://de.wikipedia.org/wiki/Cobalamine" title="Cobalamine – German" lang="de" hreflang="de" data-title="Cobalamine" data-language-autonym="Deutsch" data-language-local-name="German" class="interlanguage-link-target">Deutsch</a></li><li class="interlanguage-link interwiki-dv mw-list-item"><a href="https://dv.wikipedia.org/wiki/%DE%88%DE%A8%DE%93%DE%A6%DE%89%DE%A8%DE%82%DE%B0_%DE%84%DE%A912" title="ވިޓަމިން ބީ12 – Divehi" lang="dv" hreflang="dv" data-title="ވިޓަމިން ބީ12" data-language-autonym="ދިވެހިބަސް" data-language-local-name="Divehi" class="interlanguage-link-target">ދިވެހިބަސް</a></li><li class="interlanguage-link interwiki-et mw-list-item"><a href="https://et.wikipedia.org/wiki/B12-vitamiin" title="B12-vitamiin – Estonian" lang="et" hreflang="et" data-title="B12-vitamiin" data-language-autonym="Eesti" data-language-local-name="Estonian" class="interlanguage-link-target">Eesti</a></li><li class="interlanguage-link interwiki-el mw-list-item"><a href="https://el.wikipedia.org/wiki/%CE%92%CE%B9%CF%84%CE%B1%CE%BC%CE%AF%CE%BD%CE%B7_%CE%9212" title="Βιταμίνη Β12 – Greek" lang="el" hreflang="el" data-title="Βιταμίνη Β12" data-language-autonym="Ελληνικά" data-language-local-name="Greek" class="interlanguage-link-target">Ελληνικά</a></li><li class="interlanguage-link interwiki-es mw-list-item"><a href="https://es.wikipedia.org/wiki/Vitamina_B12" title="Vitamina B12 – Spanish" lang="es" hreflang="es" data-title="Vitamina B12" data-language-autonym="Español" data-language-local-name="Spanish" class="interlanguage-link-target">Español</a></li><li class="interlanguage-link interwiki-eo mw-list-item"><a href="https://eo.wikipedia.org/wiki/Kobalamino" title="Kobalamino – Esperanto" lang="eo" hreflang="eo" data-title="Kobalamino" data-language-autonym="Esperanto" data-language-local-name="Esperanto" class="interlanguage-link-target">Esperanto</a></li><li class="interlanguage-link interwiki-eu mw-list-item"><a href="https://eu.wikipedia.org/wiki/B12_bitamina" title="B12 bitamina – Basque" lang="eu" hreflang="eu" data-title="B12 bitamina" data-language-autonym="Euskara" data-language-local-name="Basque" class="interlanguage-link-target">Euskara</a></li><li class="interlanguage-link interwiki-fa mw-list-item"><a href="https://fa.wikipedia.org/wiki/%D9%88%DB%8C%D8%AA%D8%A7%D9%85%DB%8C%D9%86_%D8%A8%DB%B1%DB%B2" title="ویتامین ب۱۲ – Persian" lang="fa" hreflang="fa" data-title="ویتامین ب۱۲" data-language-autonym="فارسی" data-language-local-name="Persian" class="interlanguage-link-target">فارسی</a></li><li class="interlanguage-link interwiki-fr mw-list-item"><a href="https://fr.wikipedia.org/wiki/Vitamine_B12" title="Vitamine B12 – French" lang="fr" hreflang="fr" data-title="Vitamine B12" data-language-autonym="Français" data-language-local-name="French" class="interlanguage-link-target">Français</a></li><li class="interlanguage-link interwiki-gl mw-list-item"><a href="https://gl.wikipedia.org/wiki/Cobalamina" title="Cobalamina – Galician" lang="gl" hreflang="gl" data-title="Cobalamina" data-language-autonym="Galego" data-language-local-name="Galician" class="interlanguage-link-target">Galego</a></li><li class="interlanguage-link interwiki-ko mw-list-item"><a href="https://ko.wikipedia.org/wiki/%EB%B9%84%ED%83%80%EB%AF%BC_B12" title="비타민 B12 – Korean" lang="ko" hreflang="ko" data-title="비타민 B12" data-language-autonym="한국어" data-language-local-name="Korean" class="interlanguage-link-target">한국어</a></li><li class="interlanguage-link interwiki-hy mw-list-item"><a href="https://hy.wikipedia.org/wiki/%D5%8E%D5%AB%D5%BF%D5%A1%D5%B4%D5%AB%D5%B6_B12" title="Վիտամին B12 – Armenian" lang="hy" hreflang="hy" data-title="Վիտամին B12" data-language-autonym="Հայերեն" data-language-local-name="Armenian" class="interlanguage-link-target">Հայերեն</a></li><li class="interlanguage-link interwiki-hi mw-list-item"><a href="https://hi.wikipedia.org/wiki/%E0%A4%B5%E0%A4%BF%E0%A4%9F%E0%A4%BE%E0%A4%AE%E0%A4%BF%E0%A4%A8_%E0%A4%AC%E0%A5%80%E0%A5%A7%E0%A5%A8" title="विटामिन बी१२ – Hindi" lang="hi" hreflang="hi" data-title="विटामिन बी१२" data-language-autonym="हिन्दी" data-language-local-name="Hindi" class="interlanguage-link-target">हिन्दी</a></li><li class="interlanguage-link interwiki-hr mw-list-item"><a href="https://hr.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Croatian" lang="hr" hreflang="hr" data-title="Vitamin B12" data-language-autonym="Hrvatski" data-language-local-name="Croatian" class="interlanguage-link-target">Hrvatski</a></li><li class="interlanguage-link interwiki-id mw-list-item"><a href="https://id.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Indonesian" lang="id" hreflang="id" data-title="Vitamin B12" data-language-autonym="Bahasa Indonesia" data-language-local-name="Indonesian" class="interlanguage-link-target">Bahasa Indonesia</a></li><li class="interlanguage-link interwiki-is mw-list-item"><a href="https://is.wikipedia.org/wiki/B12-v%C3%ADtam%C3%ADn" title="B12-vítamín – Icelandic" lang="is" hreflang="is" data-title="B12-vítamín" data-language-autonym="Íslenska" data-language-local-name="Icelandic" class="interlanguage-link-target">Íslenska</a></li><li class="interlanguage-link interwiki-it mw-list-item"><a href="https://it.wikipedia.org/wiki/Cobalamina" title="Cobalamina – Italian" lang="it" hreflang="it" data-title="Cobalamina" data-language-autonym="Italiano" data-language-local-name="Italian" class="interlanguage-link-target">Italiano</a></li><li class="interlanguage-link interwiki-he mw-list-item"><a href="https://he.wikipedia.org/wiki/%D7%95%D7%99%D7%98%D7%9E%D7%99%D7%9F_B12" title="ויטמין B12 – Hebrew" lang="he" hreflang="he" data-title="ויטמין B12" data-language-autonym="עברית" data-language-local-name="Hebrew" class="interlanguage-link-target">עברית</a></li><li class="interlanguage-link interwiki-jv mw-list-item"><a href="https://jv.wikipedia.org/wiki/Vitamin_b12" title="Vitamin b12 – Javanese" lang="jv" hreflang="jv" data-title="Vitamin b12" data-language-autonym="Jawa" data-language-local-name="Javanese" class="interlanguage-link-target">Jawa</a></li><li class="interlanguage-link interwiki-kk mw-list-item"><a href="https://kk.wikipedia.org/wiki/%D0%9A%D0%BE%D0%B1%D0%B0%D0%BB%D0%B0%D0%BC%D0%B8%D0%BD" title="Кобаламин – Kazakh" lang="kk" hreflang="kk" data-title="Кобаламин" data-language-autonym="Қазақша" data-language-local-name="Kazakh" class="interlanguage-link-target">Қазақша</a></li><li class="interlanguage-link interwiki-rw mw-list-item"><a href="https://rw.wikipedia.org/wiki/Vitamini_B12" title="Vitamini B12 – Kinyarwanda" lang="rw" hreflang="rw" data-title="Vitamini B12" data-language-autonym="Ikinyarwanda" data-language-local-name="Kinyarwanda" class="interlanguage-link-target">Ikinyarwanda</a></li><li class="interlanguage-link interwiki-ky mw-list-item"><a href="https://ky.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_%D0%9212" title="Витамин В12 – Kyrgyz" lang="ky" hreflang="ky" data-title="Витамин В12" data-language-autonym="Кыргызча" data-language-local-name="Kyrgyz" class="interlanguage-link-target">Кыргызча</a></li><li class="interlanguage-link interwiki-lv mw-list-item"><a href="https://lv.wikipedia.org/wiki/B12_vitam%C4%ABns" title="B12 vitamīns – Latvian" lang="lv" hreflang="lv" data-title="B12 vitamīns" data-language-autonym="Latviešu" data-language-local-name="Latvian" class="interlanguage-link-target">Latviešu</a></li><li class="interlanguage-link interwiki-lb mw-list-item"><a href="https://lb.wikipedia.org/wiki/Cobalamin" title="Cobalamin – Luxembourgish" lang="lb" hreflang="lb" data-title="Cobalamin" data-language-autonym="Lëtzebuergesch" data-language-local-name="Luxembourgish" class="interlanguage-link-target">Lëtzebuergesch</a></li><li class="interlanguage-link interwiki-lt mw-list-item"><a href="https://lt.wikipedia.org/wiki/Kobalaminas" title="Kobalaminas – Lithuanian" lang="lt" hreflang="lt" data-title="Kobalaminas" data-language-autonym="Lietuvių" data-language-local-name="Lithuanian" class="interlanguage-link-target">Lietuvių</a></li><li class="interlanguage-link interwiki-hu mw-list-item"><a href="https://hu.wikipedia.org/wiki/B12-vitamin" title="B12-vitamin – Hungarian" lang="hu" hreflang="hu" data-title="B12-vitamin" data-language-autonym="Magyar" data-language-local-name="Hungarian" class="interlanguage-link-target">Magyar</a></li><li class="interlanguage-link interwiki-mk mw-list-item"><a href="https://mk.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_%D0%9112" title="Витамин Б12 – Macedonian" lang="mk" hreflang="mk" data-title="Витамин Б12" data-language-autonym="Македонски" data-language-local-name="Macedonian" class="interlanguage-link-target">Македонски</a></li><li class="interlanguage-link interwiki-ml mw-list-item"><a href="https://ml.wikipedia.org/wiki/%E0%B4%B5%E0%B4%BF%E0%B4%B1%E0%B5%8D%E0%B4%B1%E0%B4%BE%E0%B4%AE%E0%B4%BF%E0%B5%BB_%E0%B4%AC%E0%B4%BF_12" title="വിറ്റാമിൻ ബി 12 – Malayalam" lang="ml" hreflang="ml" data-title="വിറ്റാമിൻ ബി 12" data-language-autonym="മലയാളം" data-language-local-name="Malayalam" class="interlanguage-link-target">മലയാളം</a></li><li class="interlanguage-link interwiki-ms mw-list-item"><a href="https://ms.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Malay" lang="ms" hreflang="ms" data-title="Vitamin B12" data-language-autonym="Bahasa Melayu" data-language-local-name="Malay" class="interlanguage-link-target">Bahasa Melayu</a></li><li class="interlanguage-link interwiki-mn mw-list-item"><a href="https://mn.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_%D0%9212" title="Витамин В12 – Mongolian" lang="mn" hreflang="mn" data-title="Витамин В12" data-language-autonym="Монгол" data-language-local-name="Mongolian" class="interlanguage-link-target">Монгол</a></li><li class="interlanguage-link interwiki-nl mw-list-item"><a href="https://nl.wikipedia.org/wiki/Vitamine_B12" title="Vitamine B12 – Dutch" lang="nl" hreflang="nl" data-title="Vitamine B12" data-language-autonym="Nederlands" data-language-local-name="Dutch" class="interlanguage-link-target">Nederlands</a></li><li class="interlanguage-link interwiki-ja mw-list-item"><a href="https://ja.wikipedia.org/wiki/%E3%82%B3%E3%83%90%E3%83%A9%E3%83%9F%E3%83%B3" title="コバラミン – Japanese" lang="ja" hreflang="ja" data-title="コバラミン" data-language-autonym="日本語" data-language-local-name="Japanese" class="interlanguage-link-target">日本語</a></li><li class="interlanguage-link interwiki-no mw-list-item"><a href="https://no.wikipedia.org/wiki/Kobalamin" title="Kobalamin – Norwegian Bokmål" lang="nb" hreflang="nb" data-title="Kobalamin" data-language-autonym="Norsk bokmål" data-language-local-name="Norwegian Bokmål" class="interlanguage-link-target">Norsk bokmål</a></li><li class="interlanguage-link interwiki-oc mw-list-item"><a href="https://oc.wikipedia.org/wiki/Vitamina_B12" title="Vitamina B12 – Occitan" lang="oc" hreflang="oc" data-title="Vitamina B12" data-language-autonym="Occitan" data-language-local-name="Occitan" class="interlanguage-link-target">Occitan</a></li><li class="interlanguage-link interwiki-uz mw-list-item"><a href="https://uz.wikipedia.org/wiki/Vitamin_B12_(Cyanokobalamin)" title="Vitamin B12 (Cyanokobalamin) – Uzbek" lang="uz" hreflang="uz" data-title="Vitamin B12 (Cyanokobalamin)" data-language-autonym="Oʻzbekcha / ўзбекча" data-language-local-name="Uzbek" class="interlanguage-link-target">Oʻzbekcha / ўзбекча</a></li><li class="interlanguage-link interwiki-pl mw-list-item"><a href="https://pl.wikipedia.org/wiki/Witamina_B12" title="Witamina B12 – Polish" lang="pl" hreflang="pl" data-title="Witamina B12" data-language-autonym="Polski" data-language-local-name="Polish" class="interlanguage-link-target">Polski</a></li><li class="interlanguage-link interwiki-pt mw-list-item"><a href="https://pt.wikipedia.org/wiki/Vitamina_B12" title="Vitamina B12 – Portuguese" lang="pt" hreflang="pt" data-title="Vitamina B12" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target">Português</a></li><li class="interlanguage-link interwiki-ro mw-list-item"><a href="https://ro.wikipedia.org/wiki/Cobalamin%C4%83" title="Cobalamină – Romanian" lang="ro" hreflang="ro" data-title="Cobalamină" data-language-autonym="Română" data-language-local-name="Romanian" class="interlanguage-link-target">Română</a></li><li class="interlanguage-link interwiki-ru mw-list-item"><a href="https://ru.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_B12" title="Витамин B12 – Russian" lang="ru" hreflang="ru" data-title="Витамин B12" data-language-autonym="Русский" data-language-local-name="Russian" class="interlanguage-link-target">Русский</a></li><li class="interlanguage-link interwiki-sq mw-list-item"><a href="https://sq.wikipedia.org/wiki/Vitamina_B12" title="Vitamina B12 – Albanian" lang="sq" hreflang="sq" data-title="Vitamina B12" data-language-autonym="Shqip" data-language-local-name="Albanian" class="interlanguage-link-target">Shqip</a></li><li class="interlanguage-link interwiki-simple mw-list-item"><a href="https://simple.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Simple English" lang="en-simple" hreflang="en-simple" data-title="Vitamin B12" data-language-autonym="Simple English" data-language-local-name="Simple English" class="interlanguage-link-target">Simple English</a></li><li class="interlanguage-link interwiki-sk mw-list-item"><a href="https://sk.wikipedia.org/wiki/Vitam%C3%ADn_B12" title="Vitamín B12 – Slovak" lang="sk" hreflang="sk" data-title="Vitamín B12" data-language-autonym="Slovenčina" data-language-local-name="Slovak" class="interlanguage-link-target">Slovenčina</a></li><li class="interlanguage-link interwiki-sl mw-list-item"><a href="https://sl.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Slovenian" lang="sl" hreflang="sl" data-title="Vitamin B12" data-language-autonym="Slovenščina" data-language-local-name="Slovenian" class="interlanguage-link-target">Slovenščina</a></li><li class="interlanguage-link interwiki-ckb mw-list-item"><a href="https://ckb.wikipedia.org/wiki/%DA%A4%DB%8C%D8%AA%D8%A7%D9%85%DB%8C%D9%86_%D8%A8%DB%8C_%DB%B1%DB%B2" title="ڤیتامین بی ۱۲ – Central Kurdish" lang="ckb" hreflang="ckb" data-title="ڤیتامین بی ۱۲" data-language-autonym="کوردی" data-language-local-name="Central Kurdish" class="interlanguage-link-target">کوردی</a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/%D0%92%D0%B8%D1%82%D0%B0%D0%BC%D0%B8%D0%BD_%D0%9112" title="Витамин Б12 – Serbian" lang="sr" hreflang="sr" data-title="Витамин Б12" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target">Српски / srpski</a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Vitamin B12" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target">Srpskohrvatski / српскохрватски</a></li><li class="interlanguage-link interwiki-fi badge-Q17559452 badge-recommendedarticle mw-list-item" title="recommended article"><a href="https://fi.wikipedia.org/wiki/B12-vitamiini" title="B12-vitamiini – Finnish" lang="fi" hreflang="fi" data-title="B12-vitamiini" data-language-autonym="Suomi" data-language-local-name="Finnish" class="interlanguage-link-target">Suomi</a></li><li class="interlanguage-link interwiki-sv mw-list-item"><a href="https://sv.wikipedia.org/wiki/Kobalamin" title="Kobalamin – Swedish" lang="sv" hreflang="sv" data-title="Kobalamin" data-language-autonym="Svenska" data-language-local-name="Swedish" class="interlanguage-link-target">Svenska</a></li><li class="interlanguage-link interwiki-ta mw-list-item"><a href="https://ta.wikipedia.org/wiki/%E0%AE%89%E0%AE%AF%E0%AE%BF%E0%AE%B0%E0%AF%8D%E0%AE%9A%E0%AF%8D%E0%AE%9A%E0%AE%A4%E0%AF%8D%E0%AE%A4%E0%AF%81_%E0%AE%AA%E0%AE%BF12" title="உயிர்ச்சத்து பி12 – Tamil" lang="ta" hreflang="ta" data-title="உயிர்ச்சத்து பி12" data-language-autonym="தமிழ்" data-language-local-name="Tamil" class="interlanguage-link-target">தமிழ்</a></li><li class="interlanguage-link interwiki-te mw-list-item"><a href="https://te.wikipedia.org/wiki/%E0%B0%B5%E0%B0%BF%E0%B0%9F%E0%B0%AE%E0%B0%BF%E0%B0%A8%E0%B1%8D_%E0%B0%AC%E0%B1%8012" title="విటమిన్ బీ12 – Telugu" lang="te" hreflang="te" data-title="విటమిన్ బీ12" data-language-autonym="తెలుగు" data-language-local-name="Telugu" class="interlanguage-link-target">తెలుగు</a></li><li class="interlanguage-link interwiki-th mw-list-item"><a href="https://th.wikipedia.org/wiki/%E0%B8%A7%E0%B8%B4%E0%B8%95%E0%B8%B2%E0%B8%A1%E0%B8%B4%E0%B8%99%E0%B8%9A%E0%B8%B512" title="วิตามินบี12 – Thai" lang="th" hreflang="th" data-title="วิตามินบี12" data-language-autonym="ไทย" data-language-local-name="Thai" class="interlanguage-link-target">ไทย</a></li><li class="interlanguage-link interwiki-tr mw-list-item"><a href="https://tr.wikipedia.org/wiki/B12_vitamini" title="B12 vitamini – Turkish" lang="tr" hreflang="tr" data-title="B12 vitamini" data-language-autonym="Türkçe" data-language-local-name="Turkish" class="interlanguage-link-target">Türkçe</a></li><li class="interlanguage-link interwiki-uk mw-list-item"><a href="https://uk.wikipedia.org/wiki/%D0%92%D1%96%D1%82%D0%B0%D0%BC%D1%96%D0%BD_B12" title="Вітамін B12 – Ukrainian" lang="uk" hreflang="uk" data-title="Вітамін B12" data-language-autonym="Українська" data-language-local-name="Ukrainian" class="interlanguage-link-target">Українська</a></li><li class="interlanguage-link interwiki-ur mw-list-item"><a href="https://ur.wikipedia.org/wiki/%D9%88%D9%B9%D8%A7%D9%85%D9%86_%D8%A8%DB%8C_12" title="وٹامن بی 12 – Urdu" lang="ur" hreflang="ur" data-title="وٹامن بی 12" data-language-autonym="اردو" data-language-local-name="Urdu" class="interlanguage-link-target">اردو</a></li><li class="interlanguage-link interwiki-vi mw-list-item"><a href="https://vi.wikipedia.org/wiki/Vitamin_B12" title="Vitamin B12 – Vietnamese" lang="vi" hreflang="vi" data-title="Vitamin B12" data-language-autonym="Tiếng Việt" data-language-local-name="Vietnamese" class="interlanguage-link-target">Tiếng Việt</a></li><li class="interlanguage-link interwiki-wuu mw-list-item"><a href="https://wuu.wikipedia.org/wiki/%E7%BB%B4%E7%94%9F%E7%B4%A0B12" title="维生素B12 – Wu" lang="wuu" hreflang="wuu" data-title="维生素B12" data-language-autonym="吴语" data-language-local-name="Wu" class="interlanguage-link-target">吴语</a></li><li class="interlanguage-link interwiki-zh-yue mw-list-item"><a href="https://zh-yue.wikipedia.org/wiki/%E7%B6%AD%E4%BB%96%E5%91%BDB12" title="維他命B12 – Cantonese" lang="yue" hreflang="yue" data-title="維他命B12" data-language-autonym="粵語" data-language-local-name="Cantonese" class="interlanguage-link-target">粵語</a></li><li class="interlanguage-link interwiki-zh mw-list-item"><a href="https://zh.wikipedia.org/wiki/%E7%BB%B4%E7%94%9F%E7%B4%A0B12" title="维生素B12 – Chinese" lang="zh" hreflang="zh" data-title="维生素B12" data-language-autonym="中文" data-language-local-name="Chinese" class="interlanguage-link-target">中文</a></li> </ul> <div class="after-portlet after-portlet-lang"><a 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Click here for more information."><img alt="This is a good article. Click here for more information." src="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/19px-Symbol_support_vote.svg.png" decoding="async" width="19" height="20" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/29px-Symbol_support_vote.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/9/94/Symbol_support_vote.svg/39px-Symbol_support_vote.svg.png 2x" data-file-width="180" data-file-height="185" /></a></div></div> </div> <div id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Vitamin used in animal cells' metabolism</div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">This article is about the family of vitamers. For individual forms, see <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a>, <a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">cyanocobalamin</a>, <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a>, and <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a>.</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">"B12" and "Cbl" redirect here. For other uses of B12, see <a href="/wiki/B12_(disambiguation)" class="mw-disambig" title="B12 (disambiguation)">B12 (disambiguation)</a>. For the musical group, see <a href="/wiki/Carbon_Based_Lifeforms" title="Carbon Based Lifeforms">Carbon Based Lifeforms</a>.</div> <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">Vitamin B12</caption><tbody><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Cobalamin_skeletal.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Cobalamin_skeletal.svg/200px-Cobalamin_skeletal.svg.png" decoding="async" width="200" height="236" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Cobalamin_skeletal.svg/300px-Cobalamin_skeletal.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Cobalamin_skeletal.svg/400px-Cobalamin_skeletal.svg.png 2x" data-file-width="512" data-file-height="605" /></a><div class="infobox-caption">General <a href="/wiki/Skeletal_formula" title="Skeletal formula">skeletal formula</a> of cobalamins</div></td></tr><tr><td colspan="2" class="infobox-image notheme" style="background-color: #f8f9fa;"><a href="/wiki/File:Cyanocobalamin-from-xtal-3D-st-noH.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/200px-Cyanocobalamin-from-xtal-3D-st-noH.png" decoding="async" width="200" height="158" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/300px-Cyanocobalamin-from-xtal-3D-st-noH.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/0/03/Cyanocobalamin-from-xtal-3D-st-noH.png/400px-Cyanocobalamin-from-xtal-3D-st-noH.png 2x" data-file-width="2524" data-file-height="2000" /></a><div class="infobox-caption"><a href="/wiki/Ball-and-stick_model" title="Ball-and-stick model">Stick model</a> of <a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">cyanocobalamin</a> (R = CN) based on the crystal structure<a href="#cite_note-1">[1]</a></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">Other names</th><td class="infobox-data">Vitamin B12, vitamin B-12, cobalamin</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"><a rel="nofollow" class="external text" href="https://www.drugs.com/monograph/vitamin_b12.html">Monograph</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/MedlinePlus" title="MedlinePlus">MedlinePlus</a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://medlineplus.gov/druginfo/meds/a605007.html">a605007</a></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"><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><abbr class="country-name" title="United States">US</abbr> <a href="/wiki/DailyMed" title="DailyMed">DailyMed</a>: <a rel="nofollow" class="external text" href="https://dailymed.nlm.nih.gov/dailymed/search.cfm?labeltype=all&query=Vitamin_b12">Vitamin_b12</a></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 administration</a></th><td class="infobox-data"><a href="/wiki/Oral_administration" title="Oral administration">By mouth</a>, sublingual, <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> (IV), <a href="/wiki/Intramuscular" class="mw-redirect" title="Intramuscular">intramuscular</a> (IM), intranasal</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_B03" title="ATC code B03">B03BA01</a> (<a rel="nofollow" class="external text" href="https://www.whocc.no/atc_ddd_index/?code=B03BA01">WHO</a>) </li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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><abbr class="country-name" title="United Kingdom">UK</abbr>: OTC</li> <li><abbr class="country-name" title="United States">US</abbr>: <a href="/wiki/Over-the-counter_drug" title="Over-the-counter drug">OTC</a></li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">Readily absorbed in distal half of the ileum.</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Plasma_protein_binding" title="Plasma protein binding">Protein binding</a></th><td class="infobox-data">Very high to specific <a href="/wiki/Transcobalamins" class="mw-redirect" title="Transcobalamins">transcobalamins</a> plasma proteins. Binding of <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a> is slightly higher than cyanocobalamin.</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data"><a href="/wiki/Liver" title="Liver">Liver</a></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination half-life</a></th><td class="infobox-data">Approximately 6 days (400 days in the liver).</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data"><a href="/wiki/Kidney" title="Kidney">Kidney</a></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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%;">α-(5,6-Dimethylbenzimidazolyl)cobamidcyanide</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><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=68-19-9">68-19-9</a></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> <abbr title="Compound ID">CID</abbr></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409"><div class="plainlist"><ul><li><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/184933">184933</a></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><a rel="nofollow" class="external text" href="https://www.drugbank.ca/drugs/DB00115">DB00115</a></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><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.10469504.html">10469504</a></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><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/P6YC3EG204">P6YC3EG204</a></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><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/D00166">D00166</a></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><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL2110563">ChEMBL2110563</a></li></ul></div></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd">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">C63H88CoN14O14P</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">1355.388 g·mol−1</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><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=NC%28%3DO%29C%5BC%40%40%5D8%28C%29%5BC%40H%5D%28CCC%28N%29%3DO%29C%3D2%2FN%3DC8%2FC%28%2FC%29%3DC1%2F%5BC%40%40H%5D%28CCC%28N%29%3DO%29%5BC%40%5D%28C%29%28CC%28N%29%3DO%29%5BC%40%40%5D%28C%29%28N1%5BCo%2B%5DC%23N%29%5BC%40%40H%5D7%2FN%3DC%28C%28%5CC%29%3DC3%2FN%3DC%28%2FC%3D2%29C%28C%29%28C%29%5BC%40%40H%5D3CCC%28N%29%3DO%29%5BC%40%5D%28C%29%28CCC%28%3DO%29NCC%28C%29OP%28%5BO-%5D%29%28%3DO%29O%5BC%40%40H%5D6%5BC%40%40H%5D%28CO%29O%5BC%40H%5D%28n5cnc4cc%28C%29c%28C%29cc45%29%5BC%40%40H%5D6O%29%5BC%40H%5D7CC%28N%29%3DO">Interactive image</a></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%;">NC(=O)C[C@@]8(C)[C@H](CCC(N)=O)C=2/N=C8/C(/C)=C1/[C@@H](CCC(N)=O)[C@](C)(CC(N)=O)[C@@](C)(N1[Co+]C#N)[C@@H]7/N=C(C(\C)=C3/N=C(/C=2)C(C)(C)[C@@H]3CCC(N)=O)[C@](C)(CCC(=O)NCC(C)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@H](n5cnc4cc(C)c(C)cc45)[C@@H]6O)[C@H]7CC(N)=O</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/C62H90N13O14P.CN.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72–42)32(4)54(59)73–56;1–2;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);;/q;;+2/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1 <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" />Y</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:RMRCNWBMXRMIRW-WYVZQNDMSA-L <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" />Y</div></li></ul> </div></td></tr></tbody></table> Vitamin B12, also known as cobalamin, is a water-soluble <a href="/wiki/Vitamin" title="Vitamin">vitamin</a> involved in <a href="/wiki/Metabolism" title="Metabolism">metabolism</a>.<a href="#cite_note-Ods-2">[2]</a> It is one of eight <a href="/wiki/B_vitamins" title="B vitamins">B vitamins</a>. It is required by animals, which use it as a <a href="/wiki/Cofactor_(biochemistry)" title="Cofactor (biochemistry)">cofactor</a> in <a href="/wiki/DNA_synthesis" title="DNA synthesis">DNA synthesis</a>, and in both <a href="/wiki/Fatty_acid_metabolism" title="Fatty acid metabolism">fatty acid</a> and <a href="/wiki/Amino_acid_metabolism" class="mw-redirect" title="Amino acid metabolism">amino acid metabolism</a>.<a href="#cite_note-3">[3]</a> It is important in the normal functioning of the <a href="/wiki/Nervous_system" title="Nervous system">nervous system</a> via its role in the <a href="/wiki/Myelinogenesis" title="Myelinogenesis">synthesis of myelin</a>, and in the <a href="/wiki/Circulatory_system" title="Circulatory system">circulatory system</a> in the maturation of <a href="/wiki/Red_blood_cell" title="Red blood cell">red blood cells</a> in the <a href="/wiki/Bone_marrow" title="Bone marrow">bone marrow</a>.<a href="#cite_note-Ods-2">[2]</a><a href="#cite_note-Calderon2020-4">[4]</a> Plants do not need cobalamin and carry out the reactions with enzymes that are not dependent on it.<a href="#cite_note-Smith2019-5">[5]</a> Vitamin B12 is the most chemically complex of all vitamins,<a href="#cite_note-lpi-6">[6]</a> and for humans the only vitamin that must be sourced from animal-derived foods or supplements.<a href="#cite_note-Ods-2">[2]</a><a href="#cite_note-Vincenti-7">[7]</a> Only some <a href="/wiki/Archaea" title="Archaea">archaea</a> and <a href="/wiki/Bacteria" title="Bacteria">bacteria</a> can synthesize vitamin B12.<a href="#cite_note-Watanabe-8">[8]</a> <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">Vitamin B12 deficiency</a> is a widespread condition that is particularly prevalent in populations with low consumption of animal foods. Such diets can be due to a variety of reasons, such as low socioeconomic status, ethical considerations, or lifestyle choices such as <a href="/wiki/Veganism" title="Veganism">veganism</a>.<a href="#cite_note-pmid31316992-9">[9]</a> Foods containing vitamin B12 include meat, <a href="/wiki/Shellfish" title="Shellfish">shellfish</a>, <a href="/wiki/Liver_(food)" title="Liver (food)">liver</a>, fish, <a href="/wiki/Poultry" title="Poultry">poultry</a>, <a href="/wiki/Egg_as_food" class="mw-redirect" title="Egg as food">eggs</a>, and <a href="/wiki/Dairy_product" title="Dairy product">dairy products</a>.<a href="#cite_note-Ods-2">[2]</a> Many <a href="/wiki/Breakfast_cereal" title="Breakfast cereal">breakfast cereals</a> are <a href="/wiki/Food_fortification" title="Food fortification">fortified</a> with the vitamin.<a href="#cite_note-Ods-2">[2]</a> <a href="/wiki/Dietary_supplement" title="Dietary supplement">Supplements</a> and medications are available to treat and prevent vitamin B12 deficiency.<a href="#cite_note-Ods-2">[2]</a> They are usually taken by mouth, but for the treatment of deficiency may also be given as an <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<a href="#cite_note-Ods-2">[2]</a><a href="#cite_note-lpi-6">[6]</a> Vitamin B12 deficiencies have a greater effect on young children, pregnant and elderly people, and are more common in middle and lower developed countries due to malnutrition.<a href="#cite_note-:0-10">[10]</a> The most common cause of vitamin B12 deficiency in developed countries is <a href="/wiki/Malabsorption" title="Malabsorption">impaired absorption</a> due to a loss of <a href="/wiki/Intrinsic_factor" title="Intrinsic factor">gastric intrinsic factor</a> (IF) which must be bound to a food-source of B12 in order for absorption to occur.<a href="#cite_note-PKIN2020VitB12-11">[11]</a> A second major cause is an age-related decline in <a href="/wiki/Gastric_acid" title="Gastric acid">stomach acid</a> production (<a href="/wiki/Achlorhydria" title="Achlorhydria">achlorhydria</a>), because acid exposure frees protein-bound vitamin.<a href="#cite_note-DRItext-12">[12]</a> For the same reason, people on long-term antacid therapy, using <a href="/wiki/Proton-pump_inhibitors" class="mw-redirect" title="Proton-pump inhibitors">proton-pump inhibitors</a>,<a href="#cite_note-Choudhury2023-13">[13]</a> <a href="/wiki/H2_blocker" class="mw-redirect" title="H2 blocker">H2 blockers</a> or other antacids are at increased risk.<a href="#cite_note-14">[14]</a> The diets of vegetarians and vegans may not provide sufficient B12 unless a dietary supplement is taken.<a href="#cite_note-Ods-2">[2]</a> A deficiency may be characterized by limb <a href="/wiki/Neuropathy" class="mw-redirect" title="Neuropathy">neuropathy</a> or a blood disorder called <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, <a href="/wiki/Megaloblastic_anemia" title="Megaloblastic anemia">a type of anemia</a> in which red blood cells become abnormally large.<a href="#cite_note-Ods-2">[2]</a> This can result in <a href="/wiki/Fatigue" title="Fatigue">fatigue</a>, decreased ability to think, lightheadedness, shortness of breath, frequent <a href="/wiki/Infection" title="Infection">infections</a>, <a href="/wiki/Anorexia_(symptom)" title="Anorexia (symptom)">poor appetite</a>, <a href="/wiki/Paresthesia" title="Paresthesia">numbness</a> in the hands and feet, depression, memory loss, confusion, <a href="/wiki/Ataxia" title="Ataxia">difficulty walking</a>, <a href="/wiki/Optic_neuropathy" title="Optic neuropathy">blurred vision</a>, irreversible nerve damage, and many others.<a href="#cite_note-HopkinsMedicine-15">[15]</a> If left untreated in infants, deficiency may lead to neurological damage and anemia.<a href="#cite_note-Ods-2">[2]</a> <a href="/wiki/Folate" title="Folate">Folate</a> levels in the individual may affect the course of pathological changes and symptomatology of vitamin B12 deficiency. Vitamin B12 deficiency in pregnant women is strongly associated with an increased risk of spontaneous abortion, congenital malformations such as neural tube defects, problems with brain development growth in the unborn child.<a href="#cite_note-:0-10">[10]</a> Vitamin B12 was discovered as a result of pernicious anemia, an <a href="/wiki/Autoimmune_disorder" class="mw-redirect" title="Autoimmune disorder">autoimmune disorder</a> in which the blood has a lower than normal number of red blood cells, due to a deficiency of vitamin B12.<a href="#cite_note-Smith2019-5">[5]</a><a href="#cite_note-16">[16]</a> The ability to absorb the vitamin declines with age, especially in people over 60.<a href="#cite_note-17">[17]</a> <style data-mw-deduplicate="TemplateStyles:r886046785">.mw-parser-output .toclimit-2 .toclevel-1 ul,.mw-parser-output .toclimit-3 .toclevel-2 ul,.mw-parser-output .toclimit-4 .toclevel-3 ul,.mw-parser-output .toclimit-5 .toclevel-4 ul,.mw-parser-output .toclimit-6 .toclevel-5 ul,.mw-parser-output .toclimit-7 .toclevel-6 ul{display:none}</style><div class="toclimit-3"><meta property="mw:PageProp/toc" /></div> <div class="mw-heading mw-heading2"><h2 id="Definition">Definition</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=1" title="Edit section: Definition">edit</a>]</div> Vitamin B12 is a <a href="/wiki/Coordination_complex" title="Coordination complex">coordination complex</a> of <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>, which occupies the center of a <a href="/wiki/Corrin" title="Corrin">corrin</a> ligand and is further bound to a <a href="/wiki/Benzimidazole" title="Benzimidazole">benzimidazole</a> ligand and adenosyl group.<a href="#cite_note-18">[18]</a> A number of related species are known and these behave similarly, in particular all function as vitamins. This collection of compounds is sometimes referred to as "cobalamins". These chemical compounds have a similar molecular structure, each of which shows vitamin activity in a vitamin-deficient biological system, they are referred to as <a href="/wiki/Vitamer" title="Vitamer">vitamers</a>. The vitamin activity is as a <a href="/wiki/Coenzyme" class="mw-redirect" title="Coenzyme">coenzyme</a>, meaning that its presence is required for some enzyme-catalyzed reactions.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Banerjee2003-19">[19]</a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">cyanocobalamin</a>, the adenosyl ligand in vitamin B12 is replaced by <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>.</li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">hydroxocobalamin</a>, the adenosyl ligand in vitamin B12 is replaced by <a href="/wiki/Hydroxide" title="Hydroxide">hydroxide</a>.</li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a>, the adenosyl ligand in vitamin B12 is replaced by <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a>.</li></ul> Cyanocobalamin is a manufactured form of B12. Bacterial fermentation creates AdoB12 and MeB12, which are converted to cyanocobalamin by the addition of potassium cyanide in the presence of sodium nitrite and heat. Once consumed, cyanocobalamin is converted to the biologically active AdoB12 and MeB12. [<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>]The two bioactive forms of vitamin B 12 are <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a> in <a href="/wiki/Cytosol" title="Cytosol">cytosol</a> and <a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">adenosylcobalamin</a> in <a href="/wiki/Mitochondria" class="mw-redirect" title="Mitochondria">mitochondria</a>.[<a href="/wiki/Wikipedia:Citation_needed" title="Wikipedia:Citation needed">citation needed</a>] Cyanocobalamin is the most common form used in dietary supplements and <a href="/wiki/Food_fortification" title="Food fortification">food fortification</a> because cyanide stabilizes the molecule against degradation. Methylcobalamin is also offered as a dietary supplement.<a href="#cite_note-DRItext-12">[12]</a> There is no advantage to the use of adenosylcobalamin or methylcobalamin forms for the treatment of vitamin B12 deficiency.<a href="#cite_note-ObeidFedosov-20">[20]</a><a href="#cite_note-Paul2017-21">[21]</a><a href="#cite_note-Calderon2020-4">[4]</a> <a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a> can be injected intramuscularly to treat vitamin B12 deficiency. It can also be injected intravenously for the purpose of treating cyanide poisoning, as the hydroxyl group is displaced by cyanide, creating a non-toxic cyanocobalamin that is excreted in urine. "Pseudovitamin B12" refers to compounds that are <a href="/wiki/Corrinoid" title="Corrinoid">corrinoids</a> with a structure similar to the vitamin but without vitamin activity.<a href="#cite_note-Watanabe2018-22">[22]</a> Pseudovitamin B12 is the majority corrinoid in <a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">spirulina</a>, an algal health food sometimes erroneously claimed as having this vitamin activity.<a href="#cite_note-Watanabe1999-23">[23]</a> <div class="mw-heading mw-heading2"><h2 id="Deficiency">Deficiency</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=2" title="Edit section: Deficiency">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">Vitamin B12 deficiency</a></div> Vitamin B12 deficiency can potentially cause severe and irreversible damage, especially to the brain and nervous system.<a href="#cite_note-lpi-6">[6]</a><a href="#cite_note-24">[24]</a> Deficiency at levels only slightly lower than normal can cause a range of symptoms such as <a href="/wiki/Fatigue_(medical)" class="mw-redirect" title="Fatigue (medical)">fatigue</a>, feeling weak, <a href="/wiki/Lightheadedness" title="Lightheadedness">lightheadedness</a>, <a href="/wiki/Dizziness" title="Dizziness">dizziness</a>, breathlessness, headaches, <a href="/wiki/Mouth_ulcer" title="Mouth ulcer">mouth ulcers</a>, upset stomach, decreased appetite, difficulty walking (staggering balance problems),<a href="#cite_note-HopkinsMedicine-15">[15]</a><a href="#cite_note-25">[25]</a> muscle weakness, <a href="/wiki/Depression_(mood)" title="Depression (mood)">depression</a>, poor <a href="/wiki/Memory" title="Memory">memory</a>, poor reflexes, confusion, and pale skin, <a href="/wiki/Paresthesia" title="Paresthesia">feeling abnormal sensations</a>, among others, especially in people over age 60.<a href="#cite_note-lpi-6">[6]</a><a href="#cite_note-HopkinsMedicine-15">[15]</a><a href="#cite_note-National_Health_Service,_England-2019-26">[26]</a> Vitamin B12 deficiency can also cause symptoms of <a href="/wiki/Mania" title="Mania">mania</a> and <a href="/wiki/Psychosis" title="Psychosis">psychosis</a>.<a href="#cite_note-imajvitaminb12-27">[27]</a><a href="#cite_note-Lachner2012-28">[28]</a> Among other problems, weakened immunity, reduced fertility and interruption of blood circulation in women may occur.<a href="#cite_note-29">[29]</a> The main type of <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin B12 deficiency</a> anemia is <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>,<a href="#cite_note-NIH2011What-30">[30]</a> characterized by a <a href="/wiki/List_of_medical_triads_and_pentads" class="mw-redirect" title="List of medical triads and pentads">triad of symptoms</a>: <ol><li><a href="/wiki/Anemia" title="Anemia">Anemia</a> with bone marrow promegaloblastosis (<a href="/wiki/Megaloblastic_anemia" title="Megaloblastic anemia">megaloblastic anemia</a>). This is due to the inhibition of <a href="/wiki/DNA_synthesis" title="DNA synthesis">DNA synthesis</a> (specifically <a href="/wiki/Purines" class="mw-redirect" title="Purines">purines</a> and <a href="/wiki/Thymidine" title="Thymidine">thymidine</a>).</li> <li>Gastrointestinal symptoms: alteration in bowel motility, such as mild <a href="/wiki/Diarrhea" title="Diarrhea">diarrhea</a> or <a href="/wiki/Constipation" title="Constipation">constipation</a>, and loss of bladder or bowel control.<a href="#cite_note-Briani2013-31">[31]</a> These are thought to be due to defective DNA synthesis inhibiting replication in tissue sites with a high turnover of cells. This may also be due to the <a href="/wiki/Autoimmune" class="mw-redirect" title="Autoimmune">autoimmune</a> attack on the <a href="/wiki/Parietal_cell" title="Parietal cell">parietal cells</a> of the stomach in pernicious anemia. There is an association with <a href="/wiki/Gastric_antral_vascular_ectasia" title="Gastric antral vascular ectasia">gastric antral vascular ectasia</a> (which can be referred to as watermelon stomach), and pernicious anemia.<a href="#cite_note-32">[32]</a></li> <li>Neurological symptoms: sensory or motor deficiencies (absent reflexes, diminished vibration or soft touch sensation) and <a href="/wiki/Subacute_combined_degeneration_of_spinal_cord" title="Subacute combined degeneration of spinal cord">subacute combined degeneration of the spinal cord</a>.<a href="#cite_note-33">[33]</a> Deficiency symptoms in children include <a href="/wiki/Developmental_disability" title="Developmental disability">developmental delay</a>, <a href="/wiki/Developmental_regression" title="Developmental regression">regression</a>, <a href="/wiki/Irritability" title="Irritability">irritability</a>, <a href="/wiki/Abnormal_involuntary_movements" class="mw-redirect" title="Abnormal involuntary movements">involuntary movements</a> and <a href="/wiki/Hypotonia" title="Hypotonia">hypotonia</a>.<a href="#cite_note-34">[34]</a></li></ol> Vitamin B12 deficiency is most commonly caused by malabsorption, but can also result from low intake, immune gastritis, low presence of binding proteins, or use of certain medications.<a href="#cite_note-lpi-6">[6]</a> <a href="/wiki/Vegan" class="mw-redirect" title="Vegan">Vegans</a>—people who choose to not consume any animal-sourced foods—are at risk because plant-sourced foods do not contain the vitamin in sufficient amounts to prevent vitamin deficiency.<a href="#cite_note-MelinaCraig2016-35">[35]</a> <a href="/wiki/Vegetarianism" title="Vegetarianism">Vegetarians</a>—people who consume animal byproducts such as dairy products and eggs, but not the flesh of any animal—are also at risk. Vitamin B12 deficiency has been observed in between 40% and 80% of the vegetarian population who do not also take a vitamin B12 supplement or consume vitamin-fortified food.<a href="#cite_note-36">[36]</a> In Hong Kong and India, vitamin B12 deficiency has been found in roughly 80% of the vegan population. As with vegetarians, vegans can avoid this by consuming a dietary supplement or eating B12 fortified food such as cereal, plant-based milks, and <a href="/wiki/Nutritional_yeast" title="Nutritional yeast">nutritional yeast</a> as a regular part of their diet.<a href="#cite_note-Woo2014-37">[37]</a> The elderly are at increased risk because they tend to produce less <a href="/wiki/Stomach_acid" class="mw-redirect" title="Stomach acid">stomach acid</a> as they age, a condition known as <a href="/wiki/Achlorhydria" title="Achlorhydria">achlorhydria</a>, thereby increasing their probability of B12 deficiency due to reduced absorption.<a href="#cite_note-Ods-2">[2]</a> <a href="/wiki/Nitrous_oxide" title="Nitrous oxide">Nitrous oxide</a> overdose or overuse converts the active monovalent form of vitamin B12 to the inactive bivalent form.<a href="#cite_note-38">[38]</a> <div class="mw-heading mw-heading3"><h3 id="Pregnancy,_lactation_and_early_childhood">Pregnancy, lactation and early childhood</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=3" title="Edit section: Pregnancy, lactation and early childhood">edit</a>]</div> The U.S. <a href="/wiki/Dietary_Reference_Intake" title="Dietary Reference Intake">Recommended Dietary Allowance (RDA)</a> for pregnancy is 2.6 <a href="/wiki/Micrograms" class="mw-redirect" title="Micrograms">micrograms</a> per day (μg/d), for lactation 2.8 μg/d. Determination of these values was based on an RDA of 2.4 μg/d for non-pregnant women, plus what will be transferred to the fetus during pregnancy and what will be delivered in breast milk.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Obeid2017-39">[39]</a>: 972  However, looking at the same scientific evidence, the <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) sets adequate intake (AI) at 4.5 μg/d for pregnancy and 5.0 μg/d for lactation.<a href="#cite_note-auto-40">[40]</a> Low maternal vitamin B12, defined as serum concentration less than 148 pmol/L, increases the risk of miscarriage, preterm birth and newborn low birth weight.<a href="#cite_note-Rogne2017-41">[41]</a><a href="#cite_note-Obeid2017-39">[39]</a> During pregnancy the <a href="/wiki/Placenta" title="Placenta">placenta</a> concentrates B12, so that newborn infants have a higher serum concentration than their mothers.<a href="#cite_note-DRItext-12">[12]</a> As it is recently absorbed vitamin content that more effectively reaches the placenta, the vitamin consumed by the mother-to-be is more important than that contained in her liver tissue.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Sebastiani2019-42">[42]</a> Women who consume little animal-sourced food, or who are vegetarian or vegan, are at higher risk of becoming vitamin depleted during pregnancy than those who consume more animal products. This depletion can lead to anemia, and also an increased risk that their breastfed infants become vitamin deficient.<a href="#cite_note-Sebastiani2019-42">[42]</a><a href="#cite_note-Obeid2017-39">[39]</a> Vitamin B12 is not one of the supplements recommended by the World Health Organization for healthy women who are pregnant,<a href="#cite_note-:0-10">[10]</a> however vitamin B12 is often suggested during pregnancy in a multivitamin along with folic acid<a href="#cite_note-43">[43]</a><a href="#cite_note-44">[44]</a> especially for pregnant mothers who follow a vegetarian or vegan diet.<a href="#cite_note-45">[45]</a> Low vitamin concentrations in human milk occur in families with low socioeconomic status or low consumption of animal products.<a href="#cite_note-Obeid2017-39">[39]</a>: 971, 973  Only a few countries, primarily in Africa, have mandatory food fortification programs for either wheat flour or maize flour; India has a voluntary fortification program.<a href="#cite_note-Map-46">[46]</a> What the nursing mother consumes is more important than her liver tissue content, as it is recently absorbed vitamin that more effectively reaches breast milk.<a href="#cite_note-Obeid2017-39">[39]</a>: 973  Breast milk B12 decreases over months of nursing in both well-nourished and vitamin-deficient mothers.<a href="#cite_note-Obeid2017-39">[39]</a>: 973–974  Exclusive or near-exclusive breastfeeding beyond six months is a strong indicator of low serum vitamin status in nursing infants. This is especially true when the vitamin status was poor during the pregnancy and if the early-introduced foods fed to the still breastfeeding infant are vegan.<a href="#cite_note-Obeid2017-39">[39]</a>: 974–975  Risk of deficiency persists if the post-weaning diet is low in animal products.<a href="#cite_note-Obeid2017-39">[39]</a>: 974–975  Signs of low vitamin levels in infants and young children can include anemia, poor physical growth and neurodevelopmental delays.<a href="#cite_note-Obeid2017-39">[39]</a>: 975  Children diagnosed with low serum B12 can be treated with intramuscular injections, then transitioned to an oral dietary supplement.<a href="#cite_note-Obeid2017-39">[39]</a>: 976  <div class="mw-heading mw-heading3"><h3 id="Gastric_bypass_surgery">Gastric bypass surgery</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=4" title="Edit section: Gastric bypass surgery">edit</a>]</div> Various methods of gastric bypass or gastric restriction surgery are used to treat morbid obesity. Roux-en-Y gastric bypass surgery (RYGB) but not sleeve gastric bypass surgery or gastric banding, increases the risk of vitamin B12 deficiency and requires preventive post-operative treatment with either injected or high-dose oral supplementation.<a href="#cite_note-Weng2015-47">[47]</a><a href="#cite_note-Majumder2013-48">[48]</a><a href="#cite_note-Mahawar2018-49">[49]</a> For post-operative oral supplementation, 1000 μg/d may be needed to prevent vitamin deficiency.<a href="#cite_note-Mahawar2018-49">[49]</a> <div class="mw-heading mw-heading3"><h3 id="Diagnosis">Diagnosis</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=5" title="Edit section: Diagnosis">edit</a>]</div> According to one review: "At present, no 'gold standard' test exists for the diagnosis of vitamin B12 deficiency and as a consequence the diagnosis requires consideration of both the clinical state of the patient and the results of investigations."<a href="#cite_note-50">[50]</a> The vitamin deficiency is typically suspected when a routine complete blood count shows anemia with an elevated <a href="/wiki/Mean_corpuscular_volume" title="Mean corpuscular volume">mean corpuscular volume</a> (MCV). In addition, on the <a href="/wiki/Peripheral_blood_smear" class="mw-redirect" title="Peripheral blood smear">peripheral blood smear</a>, <a href="/wiki/Macrocyte" class="mw-redirect" title="Macrocyte">macrocytes</a> and hypersegmented <a href="/wiki/Polymorphonuclear_leukocyte" class="mw-redirect" title="Polymorphonuclear leukocyte">polymorphonuclear leukocytes</a> may be seen. Diagnosis is supported based on vitamin B12 blood levels below 150–180 <a href="/wiki/Molar_concentration#Units" title="Molar concentration">pmol/L</a> (200–250 <a href="/wiki/Orders_of_magnitude_(mass)#Picogram" title="Orders of magnitude (mass)">pg/mL</a>) in adults.<a href="#cite_note-Devalia2014-51">[51]</a> However, serum values can be maintained while tissue B12 stores are becoming depleted. Therefore, serum B12 values above the cut-off point of deficiency do not necessarily confirm adequate B12 status.<a href="#cite_note-Ods-2">[2]</a> For this reason, elevated serum <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> over 15 micromol/L and <a href="/wiki/Methylmalonic_acid" title="Methylmalonic acid">methylmalonic acid</a> (MMA) over 0.271 micromol/L are considered better indicators of B12 deficiency, rather than relying only on the concentration of B12 in blood.<a href="#cite_note-Ods-2">[2]</a> However, elevated MMA is not conclusive, as it is seen in people with B12 deficiency, but also in elderly people who have renal insufficiency,<a href="#cite_note-Lachner2012-28">[28]</a> and elevated homocysteine is not conclusive, as it is also seen in people with folate deficiency.<a href="#cite_note-52">[52]</a> In addition, elevated methylmalonic acid levels may also be related to metabolic disorders such as <a href="/wiki/Methylmalonic_acidemia" class="mw-redirect" title="Methylmalonic acidemia">methylmalonic acidemia</a>.<a href="#cite_note-53">[53]</a> If nervous system damage is present and blood testing is inconclusive, a <a href="/wiki/Lumbar_puncture" title="Lumbar puncture">lumbar puncture</a> may be carried out to measure <a href="/wiki/Cerebrospinal_fluid" title="Cerebrospinal fluid">cerebrospinal fluid</a> B12 levels.<a href="#cite_note-54">[54]</a> Serum <a href="/wiki/Haptocorrin" title="Haptocorrin">haptocorrin</a> binds 80-90% of circulating B12, rendering it unavailable for cellular delivery by <a href="/wiki/Transcobalamin" title="Transcobalamin">transcobalamin II</a>. This is conjectured to be a circulating storage function.<a href="#cite_note-McCorvie2023-55">[55]</a> Several serious, even life-threatening diseases cause elevated serum haptocorrin, measured as abnormally high serum vitamin B12, while at the same time potentially manifesting as a symptomatic vitamin deficiency because of insufficient vitamin bound to transcobalamin II which transfers the vitamin to cells.<a href="#cite_note-Ermens2003-56">[56]</a> <div class="mw-heading mw-heading2"><h2 id="Medical_uses">Medical uses</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=6" title="Edit section: Medical uses">edit</a>]</div> <figure class="mw-default-size" typeof="mw:File/Thumb"><a href="/wiki/File:Hydroxocobalamin_Injection.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydroxocobalamin_Injection.jpg/220px-Hydroxocobalamin_Injection.jpg" decoding="async" width="220" height="267" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydroxocobalamin_Injection.jpg/330px-Hydroxocobalamin_Injection.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/69/Hydroxocobalamin_Injection.jpg/440px-Hydroxocobalamin_Injection.jpg 2x" data-file-width="1844" data-file-height="2240" /></a><figcaption>A vitamin B12 solution (hydroxocobalamin) in a multi-dose bottle, with a single dose drawn up into a syringe for injection. Preparations are usually bright red.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Treatment_of_deficiency">Treatment of deficiency</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=7" title="Edit section: Treatment of deficiency">edit</a>]</div> Severe vitamin B12 deficiency is initially corrected with daily intramuscular injections of 1000 μg of the vitamin, followed by maintenance via monthly injections of the same amount or daily oral dosing of 1000 μg. The oral daily dose is far in excess of the vitamin requirement because the normal transporter protein mediated absorption is absent, leaving only very inefficient intestinal passive absorption.<a href="#cite_note-Elangovan2022-57">[57]</a><a href="#cite_note-Andres2018-58">[58]</a> Injection side effects include skin rash, itching, chills, fever, hot flushes, nausea and dizziness. Oral maintenance treatment avoids this problem and significantly reduces cost of treatment.<a href="#cite_note-Elangovan2022-57">[57]</a><a href="#cite_note-Andres2018-58">[58]</a> <div class="mw-heading mw-heading3"><h3 id="Cyanide_poisoning">Cyanide poisoning</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=8" title="Edit section: Cyanide poisoning">edit</a>]</div> For <a href="/wiki/Cyanide" title="Cyanide">cyanide</a> poisoning, a large amount of hydroxocobalamin may be given <a href="/wiki/Intravenously" class="mw-redirect" title="Intravenously">intravenously</a> and sometimes in combination with <a href="/wiki/Sodium_thiosulfate" title="Sodium thiosulfate">sodium thiosulfate</a>.<a href="#cite_note-Hall1987-59">[59]</a><a href="#cite_note-60">[60]</a> The mechanism of action is straightforward: the hydroxycobalamin hydroxide <a href="/wiki/Ligand" title="Ligand">ligand</a> is displaced by the toxic cyanide ion, and the resulting non-toxic cyanocobalamin is excreted in <a href="/wiki/Urine" title="Urine">urine</a>.<a href="#cite_note-61">[61]</a> <div class="mw-heading mw-heading2"><h2 id="Dietary_recommendations">Dietary recommendations</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=9" title="Edit section: Dietary recommendations">edit</a>]</div> Some research shows that most people in the United States and the United Kingdom consume sufficient vitamin B12.<a href="#cite_note-Ods-2">[2]</a><a href="#cite_note-PKIN2020VitB12-11">[11]</a> However, other research suggests that the proportion of people with low or marginal levels of vitamin B12 is up to 40% in the <a href="/wiki/Western_world" title="Western world">Western world</a>.<a href="#cite_note-Ods-2">[2]</a> <a href="/wiki/Grain" title="Grain">Grain</a>-based foods can be <a href="/wiki/Food_fortification" title="Food fortification">fortified</a> by having the vitamin added to them. Vitamin B12 supplements are available as single or multivitamin tablets. <a href="/wiki/Pharmaceutical" class="mw-redirect" title="Pharmaceutical">Pharmaceutical</a> preparations of vitamin B12 may be given by <a href="/wiki/Intramuscular_injection" title="Intramuscular injection">intramuscular injection</a>.<a href="#cite_note-lpi-6">[6]</a><a href="#cite_note-nd-62">[62]</a> Since there are few non-animal sources of the vitamin, <a href="/wiki/Vegan" class="mw-redirect" title="Vegan">vegans</a> are advised to consume a <a href="/wiki/Dietary_supplement" title="Dietary supplement">dietary supplement</a> or fortified foods for B12 intake, or risk serious health consequences.<a href="#cite_note-lpi-6">[6]</a> Children in some regions of <a href="/wiki/Developing_countries" class="mw-redirect" title="Developing countries">developing countries</a> are at particular risk due to increased requirements during growth coupled with diets low in animal-sourced foods. The US <a href="/wiki/National_Academy_of_Medicine" title="National Academy of Medicine">National Academy of Medicine</a> updated estimated average requirements (EARs) and recommended dietary allowances (RDAs) for vitamin B12 in 1998.<a href="#cite_note-lpi-6">[6]</a> The EAR for vitamin B12 for women and men ages 14 and up is 2.0 μg/day; the RDA is 2.4 μg/d. RDA is higher than EAR so as to identify amounts that will cover people with higher than average requirements. RDA for pregnancy equals 2.6 μg/day. RDA for lactation equals 2.8 μg/d. For infants up to 12 months the adequate intake (AI) is 0.4–0.5 μg/day. (AIs are established when there is insufficient information to determine EARs and RDAs.) For children ages 1–13 years the RDA increases with age from 0.9 to 1.8 μg/day. Because 10 to 30 percent of older people may be unable to effectively absorb vitamin B12 naturally occurring in foods, it is advisable for those older than 50 years to meet their RDA mainly by consuming foods fortified with vitamin B12 or a supplement containing vitamin B12. As for safety, <a href="/wiki/Tolerable_upper_intake_level" class="mw-redirect" title="Tolerable upper intake level">tolerable upper intake levels</a> (known as ULs) are set for vitamins and minerals when evidence is sufficient. In the case of vitamin B12 there is no UL, as there is no human data for adverse effects from high doses. Collectively the EARs, RDAs, AIs and ULs are referred to as <a href="/wiki/Dietary_reference_intake" class="mw-redirect" title="Dietary reference intake">dietary reference intakes</a> (DRIs).<a href="#cite_note-DRItext-12">[12]</a> The <a href="/wiki/European_Food_Safety_Authority" title="European Food Safety Authority">European Food Safety Authority</a> (EFSA) refers to the collective set of information as "dietary reference values", with population reference intake (PRI) instead of RDA, and average requirement instead of EAR. AI and UL are defined by EFSA the same as in the United States. For women and men over age 18 the adequate intake (AI) is set at 4.0 μg/day. AI for pregnancy is 4.5 μg/day, for lactation 5.0 μg/day. For children aged 1–14 years the AIs increase with age from 1.5 to 3.5 μg/day. These AIs are higher than the U.S. RDAs.<a href="#cite_note-auto-40">[40]</a> The EFSA also reviewed the safety question and reached the same conclusion as in the United States—that there was not sufficient evidence to set a UL for vitamin B12.<a href="#cite_note-63">[63]</a> The Japan National Institute of Health and Nutrition set the RDA for people ages 12 and older at 2.4 μg/day.<a href="#cite_note-64">[64]</a> The <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> also uses 2.4 μg/day as the adult recommended nutrient intake for this vitamin.<a href="#cite_note-65">[65]</a> For U.S. food and dietary supplement labeling purposes, the amount in a serving is expressed as a "percent of daily value" (%DV). For vitamin B12 labeling purposes, 100% of the daily value was 6.0 μg, but on May 27, 2016, it was revised downward to 2.4 μg.<a href="#cite_note-FedReg-66">[66]</a><a href="#cite_note-67">[67]</a> Compliance with the updated labeling regulations was required by 1 January 2020 for manufacturers with <a href="/wiki/US$" class="mw-redirect" title="US$">US$</a>10 million or more in annual food sales, and by 1 January 2021 for manufacturers with lower volume food sales.<a href="#cite_note-FDAdelay-68">[68]</a><a href="#cite_note-69">[69]</a> A table of the old and new adult daily values is provided at <a href="/wiki/Reference_Daily_Intake" title="Reference Daily Intake">Reference Daily Intake</a>. <div class="mw-heading mw-heading2"><h2 id="Sources">Sources</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=10" title="Edit section: Sources">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Bacteria_and_archaea">Bacteria and archaea</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=11" title="Edit section: Bacteria and archaea">edit</a>]</div> Vitamin B12 is produced in nature by certain <a href="/wiki/Bacteria" title="Bacteria">bacteria</a>, and <a href="/wiki/Archaea" title="Archaea">archaea</a>.<a href="#cite_note-70">[70]</a><a href="#cite_note-71">[71]</a><a href="#cite_note-72">[72]</a> It is synthesized by some bacteria in the <a href="/wiki/Gut_microbiota" title="Gut microbiota">gut microbiota</a> in humans and other animals, but it has long been thought that humans cannot absorb this as it is made in the <a href="/wiki/Large_intestine" title="Large intestine">colon</a>, downstream from the <a href="/wiki/Small_intestine" title="Small intestine">small intestine</a>, where the absorption of most nutrients occurs.<a href="#cite_note-Gille2015rev-73">[73]</a> <a href="/wiki/Ruminant" title="Ruminant">Ruminants</a>, such as cows and sheep, are foregut fermenters, meaning that plant food undergoes microbial fermentation in the <a href="/wiki/Rumen" title="Rumen">rumen</a> before entering the true stomach (<a href="/wiki/Abomasum" title="Abomasum">abomasum</a>), and thus they are absorbing vitamin B12 produced by bacteria.<a href="#cite_note-Gille2015rev-73">[73]</a><a href="#cite_note-Stevens1998-74">[74]</a> Other mammalian species (examples: <a href="/wiki/Rabbit" title="Rabbit">rabbits</a>, <a href="/wiki/Pika" title="Pika">pikas</a>, <a href="/wiki/Beaver" title="Beaver">beaver</a>, <a href="/wiki/Guinea_pigs" class="mw-redirect" title="Guinea pigs">guinea pigs</a>) consume high-fibre plants which pass through the gastrointestinal tract and undergo bacterial fermentation in the <a href="/wiki/Cecum" title="Cecum">cecum</a> and <a href="/wiki/Large_intestine" title="Large intestine">large intestine</a>. In this <a href="/wiki/Hindgut_fermentation" title="Hindgut fermentation">hindgut fermentation</a>, the material from the cecum is expelled as "<a href="/wiki/Cecotrope" title="Cecotrope">cecotropes</a>" and are re-ingested, a practice referred to as <a href="/wiki/Cecotrope" title="Cecotrope">cecotrophy</a>. Re-ingestion allows for absorption of nutrients made available by bacterial fermentation, and also of vitamins and other nutrients synthesized by the gut bacteria, including vitamin B12.<a href="#cite_note-Stevens1998-74">[74]</a> Non-ruminant, non-hindgut herbivores may have an enlarged forestomach and/or small intestine to provide a place for bacterial fermentation and B-vitamin production, including B12.<a href="#cite_note-Stevens1998-74">[74]</a> For gut bacteria to produce vitamin B12, the animal must consume sufficient amounts of <a href="/wiki/Bush_sickness" class="mw-redirect" title="Bush sickness">cobalt</a>.<a href="#cite_note-McDowell-75">[75]</a> Soil that is deficient in cobalt may result in B12 deficiency, and B12 injections or cobalt supplementation may be required for livestock.<a href="#cite_note-76">[76]</a> <div class="mw-heading mw-heading3"><h3 id="Animal-derived_foods">Animal-derived foods</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=12" title="Edit section: Animal-derived foods">edit</a>]</div> Animals store vitamin B12 from their diets in their <a href="/wiki/Liver" title="Liver">livers</a> and <a href="/wiki/Muscle" title="Muscle">muscles</a> and some pass the vitamin into their <a href="/wiki/Egg_as_food" class="mw-redirect" title="Egg as food">eggs</a> and <a href="/wiki/Milk" title="Milk">milk</a>. Meat, liver, eggs and milk are therefore sources of the vitamin for other animals, including humans.<a href="#cite_note-nd-62">[62]</a><a href="#cite_note-Ods-2">[2]</a><a href="#cite_note-BPE-77">[77]</a> For humans, the <a href="/wiki/Bioavailability" title="Bioavailability">bioavailability</a> from eggs is less than 9%, compared to 40% to 60% from fish, fowl and meat.<a href="#cite_note-Watanabe-2007-78">[78]</a> Insects are a source of B12 for animals (including other insects and humans).<a href="#cite_note-BPE-77">[77]</a><a href="#cite_note-79">[79]</a> Animal-derived food sources with a high concentration of vitamin B12 include <a href="/wiki/Liver_(food)" title="Liver (food)">liver</a> and other <a href="/wiki/Organ_meat" class="mw-redirect" title="Organ meat">organ meats</a> from <a href="/wiki/Lamb_and_mutton" title="Lamb and mutton">lamb</a>, <a href="/wiki/Veal" title="Veal">veal</a>, <a href="/wiki/Beef" title="Beef">beef</a>, and <a href="/wiki/Turkey_meat" title="Turkey meat">turkey</a>; also <a href="/wiki/Shellfish" title="Shellfish">shellfish</a> and <a href="/wiki/Crab_meat" title="Crab meat">crab meat</a>.<a href="#cite_note-lpi-6">[6]</a><a href="#cite_note-nd-62">[62]</a><a href="#cite_note-USDAcontent-80">[80]</a> <div class="mw-heading mw-heading3"><h3 id="Plants_and_algae">Plants and algae</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=13" title="Edit section: Plants and algae">edit</a>]</div> There is some evidence that bacterial fermentation of plant foods and symbiotic relationships between algae and bacteria can provide vitamin B12. However, the <a href="/wiki/Academy_of_Nutrition_and_Dietetics" title="Academy of Nutrition and Dietetics">Academy of Nutrition and Dietetics</a> considers plant and algae sources "unreliable", stating that <a href="/wiki/Veganism" title="Veganism">vegans</a> should turn to fortified foods and supplements instead.<a href="#cite_note-MelinaCraig2016-35">[35]</a> Natural plant and <a href="/wiki/Algae" title="Algae">algae</a> sources of vitamin B12 include <a href="/wiki/Fermentation" title="Fermentation">fermented</a> plant foods such as <a href="/wiki/Tempeh" title="Tempeh">tempeh</a><a href="#cite_note-Keuth-81">[81]</a><a href="#cite_note-Mo-82">[82]</a> and seaweed-derived foods such as <a href="/wiki/Nori" title="Nori">nori</a> and <a href="/wiki/Laverbread" title="Laverbread">laverbread</a>.<a href="#cite_note-watanabe-83">[83]</a><a href="#cite_note-84">[84]</a><a href="#cite_note-85">[85]</a> Methylcobalamin has been identified in <a href="/wiki/Chlorella_vulgaris" title="Chlorella vulgaris">Chlorella vulgaris</a>.<a href="#cite_note-86">[86]</a> Since only bacteria and some archea possess the genes and enzymes necessary to synthesize vitamin B12, plant and algae sources all obtain the vitamin secondarily from symbiosis with various species of bacteria,<a href="#cite_note-Smith2019-5">[5]</a> or in the case of fermented plant foods, from bacterial fermentation.<a href="#cite_note-Keuth-81">[81]</a> <div class="mw-heading mw-heading3"><h3 id="Fortified_foods">Fortified foods</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=14" title="Edit section: Fortified foods">edit</a>]</div> Foods for which vitamin B12-fortified versions are available include <a href="/wiki/Breakfast_cereals" class="mw-redirect" title="Breakfast cereals">breakfast cereals</a>, plant-derived <a href="/wiki/Milk_substitute" title="Milk substitute">milk substitutes</a> such as <a href="/wiki/Soy_milk" title="Soy milk">soy milk</a> and <a href="/wiki/Oat_milk" title="Oat milk">oat milk</a>, <a href="/wiki/Energy_bar" title="Energy bar">energy bars</a>, and <a href="/wiki/Nutritional_yeast" title="Nutritional yeast">nutritional yeast</a>.<a href="#cite_note-USDAcontent-80">[80]</a> The fortification ingredient is cyanocobalamin. Microbial fermentation yields adenosylcobalamin, which is then converted to cyanocobalamin by addition of potassium cyanide or thiocyanate in the presence of sodium nitrite and heat.<a href="#cite_note-87">[87]</a> As of 2019, nineteen countries require food fortification of wheat flour, maize flour or rice with vitamin B12. Most of these are in southeast Africa or Central America.<a href="#cite_note-Map-46">[46]</a> Vegan advocacy organizations, among others, recommend that every vegan consume B12 from either fortified foods or supplements.<a href="#cite_note-lpi-6">[6]</a><a href="#cite_note-Woo2014-37">[37]</a><a href="#cite_note-88">[88]</a><a href="#cite_note-89">[89]</a> <div class="mw-heading mw-heading3"><h3 id="Supplements">Supplements</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=15" title="Edit section: Supplements">edit</a>]</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:Methylcobalamin_tablets.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Methylcobalamin_tablets.jpg/200px-Methylcobalamin_tablets.jpg" decoding="async" width="200" height="305" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/34/Methylcobalamin_tablets.jpg/300px-Methylcobalamin_tablets.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/34/Methylcobalamin_tablets.jpg/400px-Methylcobalamin_tablets.jpg 2x" data-file-width="1254" data-file-height="1914" /></a><figcaption>A blister pack of 500 μg methylcobalamin tablets</figcaption></figure> Vitamin B12 is included in multivitamin pills; in some countries grain-based foods such as bread and pasta are fortified with B12. In the US, non-prescription products can be purchased providing up to 5,000 μg each, and it is a common ingredient in <a href="/wiki/Energy_drink" title="Energy drink">energy drinks</a> and <a href="/wiki/Energy_shot" title="Energy shot">energy shots</a>, usually at many times the recommended dietary allowance of B12. The vitamin can also be supplied on prescription and delivered via injection or other means.<a href="#cite_note-Ods-2">[2]</a> <a href="/wiki/Sublingual_administration" title="Sublingual administration">Sublingual</a> <a href="/wiki/Methylcobalamin" title="Methylcobalamin">methylcobalamin</a>, which contains no <a href="/wiki/Cyanide" title="Cyanide">cyanide</a>, is available in 5 mg tablets. The metabolic fate and biological distribution of methylcobalamin are expected to be similar to that of other sources of vitamin B12 in the diet.<a href="#cite_note-EFSA-90">[90]</a> The amount of cyanide in cyanocobalamin is generally not a concern, even in the 1,000 μg dose, since the amount of cyanide there (20 μg in a 1,000 μg cyanocobalamin tablet) is less than the daily consumption of cyanide from food, and therefore cyanocobalamin is not considered a health risk.<a href="#cite_note-EFSA-90">[90]</a> <div class="mw-heading mw-heading3"><h3 id="Intramuscular_or_intravenous_injection">Intramuscular or intravenous injection</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=16" title="Edit section: Intramuscular or intravenous injection">edit</a>]</div> Injection of <a href="/wiki/Hydroxycobalamin" class="mw-redirect" title="Hydroxycobalamin">hydroxycobalamin</a> is often used if digestive absorption is impaired,<a href="#cite_note-Ods-2">[2]</a> but this course of action may not be necessary with high-dose oral supplements (such as 0.5–1.0 mg or more),<a href="#cite_note-91">[91]</a><a href="#cite_note-92">[92]</a> because with large quantities of the vitamin taken orally, even the 1% to 5% of free crystalline B12 that is absorbed along the entire intestine by passive diffusion may be sufficient to provide a necessary amount.<a href="#cite_note-93">[93]</a> A person with <a href="/w/index.php?title=Cobalamin_C_disease&action=edit&redlink=1" class="new" title="Cobalamin C disease (page does not exist)">cobalamin C disease</a> (which results in combined <a href="/wiki/Methylmalonic_aciduria" class="mw-redirect" title="Methylmalonic aciduria">methylmalonic aciduria</a> and <a href="/wiki/Homocystinuria" title="Homocystinuria">homocystinuria</a>) may require treatment with intravenous or intramuscular hydroxocobalamin or transdermal B12, because oral cyanocobalamin is inadequate in the treatment of <a href="/w/index.php?title=Cobalamin_C_disease&action=edit&redlink=1" class="new" title="Cobalamin C disease (page does not exist)">cobalamin C disease</a>.<a href="#cite_note-Thauvin-94">[94]</a> <div class="mw-heading mw-heading3"><h3 id="Nanotechnologies_used_in_vitamin_B12_supplementation">Nanotechnologies used in vitamin B12 supplementation</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=17" title="Edit section: Nanotechnologies used in vitamin B12 supplementation">edit</a>]</div> Conventional administration does not ensure specific distribution and controlled release of vitamin B12. Moreover, therapeutic protocols involving injection require health care people and commuting of patients to the hospital thus increasing the cost of the treatment and impairing the lifestyle of patients. Targeted delivery of vitamin B12 is a major focus of modern prescriptions. For example, conveying the vitamin to the bone marrow and nerve cells would help myelin recovery. Currently, several nanocarriers strategies are being developed for improving vitamin B12 delivery with the aim to simplify administration, reduce costs, improve pharmacokinetics, and ameliorate the quality of patients' lives.<a href="#cite_note-95">[95]</a> <div class="mw-heading mw-heading3"><h3 id="Pseudovitamin-B12">Pseudovitamin-B12</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=18" title="Edit section: Pseudovitamin-B12">edit</a>]</div> Pseudovitamin-B12 refers to B12-like analogues that are biologically inactive in humans.<a href="#cite_note-Watanabe2018-22">[22]</a> Most cyanobacteria, including <a href="/wiki/Spirulina_(dietary_supplement)" title="Spirulina (dietary supplement)">Spirulina</a>, and some algae, such as <a href="/wiki/Porphyra" title="Porphyra">Porphyra</a> tenera (used to make a dried seaweed food called <a href="/wiki/Nori" title="Nori">nori</a> in Japan), have been found to contain mostly pseudovitamin-B12 instead of biologically active B12.<a href="#cite_note-Watanabe1999-23">[23]</a><a href="#cite_note-Yamada_K_1999-96">[96]</a> These pseudo-vitamin compounds can be found in some types of shellfish,<a href="#cite_note-Watanabe2018-22">[22]</a> in edible insects,<a href="#cite_note-97">[97]</a> and at times as metabolic breakdown products of cyanocobalamin added to dietary supplements and fortified foods.<a href="#cite_note-Yamada_K_2008-98">[98]</a> Pseudovitamin-B12 can show up as biologically active vitamin B12 when a microbiological assay with Lactobacillus delbrueckii subsp. lactis is used, as the bacteria can utilize the pseudovitamin despite it being unavailable to humans. To get a reliable reading of B12 content, more advanced techniques are available. One such technique involves pre-separation by <a href="/wiki/Silica_gel" title="Silica gel">silica gel</a> and then assessment with B12-dependent E. coli bacteria.<a href="#cite_note-Watanabe2018-22">[22]</a> A related concept is <a href="/wiki/Antivitamin" class="mw-redirect" title="Antivitamin">antivitamin</a> B12, compounds (often synthetic B12 analogues) that not only have no vitamin action, but also actively interfere with the activity of true vitamin B12. The design of these compounds mainly involve replacement of the metal ion with <a href="/wiki/Rhodium" title="Rhodium">rhodium</a>, <a href="/wiki/Nickel" title="Nickel">nickel</a>, or <a href="/wiki/Zinc" title="Zinc">zinc</a>; or the attachment of an inactive ligand such as 4-ethylphenyl. These compounds have the potential to be used for analyzing B12 utilization pathways or even attacking B12-dependent pathogens.<a href="#cite_note-99">[99]</a> <div class="mw-heading mw-heading2"><h2 id="Drug_interactions">Drug interactions</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=19" title="Edit section: Drug interactions">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="H2-receptor_antagonists_and_proton-pump_inhibitors">H2-receptor antagonists and proton-pump inhibitors</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=20" title="Edit section: H2-receptor antagonists and proton-pump inhibitors">edit</a>]</div> Gastric acid is needed to release vitamin B12 from protein for absorption. Reduced secretion of <a href="/wiki/Gastric_acid" title="Gastric acid">gastric acid</a> and <a href="/wiki/Pepsin" title="Pepsin">pepsin</a>, from the use of <a href="/wiki/H2_antagonist" class="mw-redirect" title="H2 antagonist">H2 blocker</a> or <a href="/wiki/Proton-pump_inhibitor" title="Proton-pump inhibitor">proton-pump inhibitor</a> (PPI) drugs, can reduce absorption of protein-bound (dietary) vitamin B12, although not of supplemental vitamin B12. H2-receptor antagonist examples include <a href="/wiki/Cimetidine" title="Cimetidine">cimetidine</a>, <a href="/wiki/Famotidine" title="Famotidine">famotidine</a>, <a href="/wiki/Nizatidine" title="Nizatidine">nizatidine</a>, and <a href="/wiki/Ranitidine" title="Ranitidine">ranitidine</a>. PPIs examples include <a href="/wiki/Omeprazole" title="Omeprazole">omeprazole</a>, <a href="/wiki/Lansoprazole" title="Lansoprazole">lansoprazole</a>, <a href="/wiki/Rabeprazole" title="Rabeprazole">rabeprazole</a>, <a href="/wiki/Pantoprazole" title="Pantoprazole">pantoprazole</a>, and <a href="/wiki/Esomeprazole" title="Esomeprazole">esomeprazole</a>. Clinically significant vitamin B12 deficiency and megaloblastic anemia are unlikely, unless these drug therapies are prolonged for two or more years, or if in addition the person's dietary intake is below recommended levels. Symptomatic vitamin deficiency is more likely if the person is rendered <a href="/wiki/Achlorhydria" title="Achlorhydria">achlorhydric</a> (a complete absence of gastric acid secretion), which occurs more frequently with proton pump inhibitors than H2 blockers.<a href="#cite_note-100">[100]</a> <div class="mw-heading mw-heading3"><h3 id="Metformin">Metformin</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=21" title="Edit section: Metformin">edit</a>]</div> Reduced serum levels of vitamin B12 occur in up to 30% of people taking long-term <a href="/wiki/Anti-diabetic_medication" class="mw-redirect" title="Anti-diabetic medication">anti-diabetic</a> <a href="/wiki/Metformin" title="Metformin">metformin</a>.<a href="#cite_note-Ahmed-101">[101]</a><a href="#cite_note-102">[102]</a> Deficiency does not develop if dietary intake of vitamin B12 is adequate or prophylactic B12 supplementation is given. If the deficiency is detected, metformin can be continued while the deficiency is corrected with B12 supplements.<a href="#cite_note-103">[103]</a> <div class="mw-heading mw-heading3"><h3 id="Other_drugs">Other drugs</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=22" title="Edit section: Other drugs">edit</a>]</div> Certain medications can decrease the absorption of orally consumed vitamin B12, including <a href="/wiki/Colchicine" title="Colchicine">colchicine</a>, extended-release <a href="/wiki/Potassium" title="Potassium">potassium</a> products, and antibiotics such as <a href="/wiki/Gentamicin" title="Gentamicin">gentamicin</a>, <a href="/wiki/Neomycin" title="Neomycin">neomycin</a> and <a href="/wiki/Tobramycin" title="Tobramycin">tobramycin</a>.<a href="#cite_note-WebMD-104">[104]</a> Anti-seizure medications <a href="/wiki/Phenobarbital" title="Phenobarbital">phenobarbital</a>, <a href="/wiki/Pregabalin" title="Pregabalin">pregabalin</a>, <a href="/wiki/Primidone" title="Primidone">primidone</a> and <a href="/wiki/Topiramate" title="Topiramate">topiramate</a> are associated with lower than normal serum vitamin concentration. However, serum levels were higher in people prescribed <a href="/wiki/Valproate" title="Valproate">valproate</a>.<a href="#cite_note-Linnebank2011-105">[105]</a> In addition, certain drugs may interfere with laboratory tests for the vitamin, such as <a href="/wiki/Amoxicillin" title="Amoxicillin">amoxicillin</a>, <a href="/wiki/Erythromycin" title="Erythromycin">erythromycin</a>, <a href="/wiki/Methotrexate" title="Methotrexate">methotrexate</a> and <a href="/wiki/Pyrimethamine" title="Pyrimethamine">pyrimethamine</a>.<a href="#cite_note-WebMD-104">[104]</a> <div class="mw-heading mw-heading2"><h2 id="Chemistry">Chemistry</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=23" title="Edit section: Chemistry">edit</a>]</div> <figure typeof="mw:File/Thumb"><a href="/wiki/File:B12_methylcobalamin.jpg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/B12_methylcobalamin.jpg/200px-B12_methylcobalamin.jpg" decoding="async" width="200" height="267" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/8/83/B12_methylcobalamin.jpg/300px-B12_methylcobalamin.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/8/83/B12_methylcobalamin.jpg/400px-B12_methylcobalamin.jpg 2x" data-file-width="2448" data-file-height="3264" /></a><figcaption>Methylcobalamin (shown) is a form of vitamin B12. Physically it resembles the other forms of vitamin B12, occurring as dark red crystals that freely form cherry-colored transparent solutions in water.</figcaption></figure> Vitamin B12 is the most chemically complex of all the vitamins.<a href="#cite_note-lpi-6">[6]</a> The structure of B12 is based on a <a href="/wiki/Corrin" title="Corrin">corrin</a> ring, which is similar to the <a href="/wiki/Porphyrin" title="Porphyrin">porphyrin</a> ring found in <a href="/wiki/Heme" title="Heme">heme</a>. The central metal ion is <a href="/wiki/Cobalt" title="Cobalt">cobalt</a>. As isolated as an air-stable solid and available commercially, cobalt in vitamin B12 (cyanocobalamin and other vitamers) is present in its +3 oxidation state. Biochemically, the cobalt center can take part in both two-electron and one-electron reductive processes to access the "reduced" (B12r, +2 oxidation state) and "super-reduced" (B12s, +1 oxidation state) forms. The ability to shuttle between the +1, +2, and +3 oxidation states is responsible for the versatile chemistry of vitamin B12, allowing it to serve as a donor of deoxyadenosyl radical (radical alkyl source) and as a methyl cation equivalent (electrophilic alkyl source).<a href="#cite_note-106">[106]</a> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Cobalamin-general-structure-color.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Cobalamin-general-structure-color.png/400px-Cobalamin-general-structure-color.png" decoding="async" width="400" height="264" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Cobalamin-general-structure-color.png/600px-Cobalamin-general-structure-color.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/7/7c/Cobalamin-general-structure-color.png/800px-Cobalamin-general-structure-color.png 2x" data-file-width="9610" data-file-height="6335" /></a><figcaption>The structures of the four most common vitamers of cobalamin, together with some synonyms. The structure of the 5'-deoxyadenosyl group, which forms the R group of adenosylcobalamin is also shown.</figcaption></figure> Four of the six coordination sites are provided by the corrin ring, and a fifth by a <a href="/wiki/Dimethylbenzimidazole" class="mw-redirect" title="Dimethylbenzimidazole">dimethylbenzimidazole</a> group. The sixth coordination site, the <a href="/wiki/Reactive_center" title="Reactive center">reactive center</a>, is variable, being a <a href="/wiki/Cyanide" title="Cyanide">cyano group</a> (–CN), a <a href="/wiki/Hydroxyl" class="mw-redirect" title="Hydroxyl">hydroxyl</a> group (–OH), a <a href="/wiki/Methyl" class="mw-redirect" title="Methyl">methyl</a> group (–CH3) or a 5′-deoxy<a href="/wiki/Adenosine" title="Adenosine">adenosyl</a> group. Historically, the covalent carbon–cobalt bond is one of the first examples of carbon–metal bonds to be discovered in biology. The <a href="/wiki/Hydrogenase" title="Hydrogenase">hydrogenases</a> and, by necessity, enzymes associated with cobalt utilization, involve metal–carbon bonds.<a href="#cite_note-107">[107]</a> Animals have the ability to convert cyanocobalamin and hydroxocobalamin to the bioactive forms adenosylcobalamin and methylcobalamin by means of enzymatically replacing the cyano or hydroxyl groups. <div class="mw-heading mw-heading3"><h3 id="Methods_for_the_analysis_of_vitamin_B12_in_food">Methods for the analysis of vitamin B12 in food</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=24" title="Edit section: Methods for the analysis of vitamin B12 in food">edit</a>]</div> Several methods have been used to determine the vitamin B12 content in foods including microbiological assays, chemiluminescence assays, polarographic, spectrophotometric and high-performance liquid chromatography processes.<a href="#cite_note-Lawrance-2015-108">[108]</a> The microbiological assay has been the most commonly used assay technique for foods, utilizing certain vitamin B12-requiring microorganisms, such as <a href="/wiki/Lactobacillus_delbrueckii_subsp._lactis" title="Lactobacillus delbrueckii subsp. lactis">Lactobacillus delbrueckii subsp. lactis</a> ATCC7830.<a href="#cite_note-Watanabe-2007-78">[78]</a> However, it is no longer the reference method due to the high measurement uncertainty of vitamin B12.<a href="#cite_note-O'Leary-2010-109">[109]</a> Furthermore, this assay requires overnight incubation and may give false results if any inactive vitamin B12 analogues are present in the foods.<a href="#cite_note-CRC_Press-2017-110">[110]</a> Currently, radioisotope dilution assay (RIDA) with labelled vitamin B12 and hog IF (pigs) have been used to determine vitamin B12 content in food.<a href="#cite_note-Watanabe-2007-78">[78]</a> Previous reports have suggested that the RIDA method is able to detect higher concentrations of vitamin B12 in foods compared to the microbiological assay method.<a href="#cite_note-Watanabe-2007-78">[78]</a><a href="#cite_note-Lawrance-2015-108">[108]</a> <div class="mw-heading mw-heading2"><h2 id="Biochemistry">Biochemistry</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=25" title="Edit section: Biochemistry">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Coenzyme_function">Coenzyme function</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=26" title="Edit section: Coenzyme function">edit</a>]</div> Vitamin B12 functions as a <a href="/wiki/Coenzyme" class="mw-redirect" title="Coenzyme">coenzyme</a>, meaning that its presence is required in some enzyme-catalyzed reactions.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Banerjee2003-19">[19]</a> Listed here are the three classes of enzymes that sometimes require B12 to function (in animals): <ol><li><a href="/wiki/Isomerase" title="Isomerase">Isomerases</a> <dl><dd>Rearrangements in which a hydrogen atom is directly transferred between two adjacent atoms with concomitant exchange of the second substituent, X, which may be a carbon atom with substituents, an oxygen atom of an alcohol, or an amine. These use the AdoB12 (adenosylcobalamin) form of the vitamin.<a href="#cite_note-Takahashi2012-111">[111]</a></dd></dl></li> <li><a href="/wiki/Methyltransferase" title="Methyltransferase">Methyltransferases</a> <dl><dd>Methyl (–CH3) group transfers between two molecules. These use the MeB12 (methylcobalamin) form of the vitamin.<a href="#cite_note-Froese2019-112">[112]</a></dd></dl></li> <li><a href="/wiki/Dehalogenase" title="Dehalogenase">Dehalogenases</a> <dl><dd>Some species of anaerobic bacteria synthesize B12-dependent dehalogenases, which have potential commercial applications for degrading chlorinated pollutants. The microorganisms may either be capable of de novo corrinoid biosynthesis or are dependent on exogenous vitamin B12.<a href="#cite_note-113">[113]</a><a href="#cite_note-114">[114]</a></dd></dl></li></ol> In humans, two major coenzyme B12-dependent enzyme families corresponding to the first two reaction types, are known. These are typified by the following two enzymes: <div class="mw-heading mw-heading4"><h4 id="Methylmalonyl-CoA_mutase">Methylmalonyl-CoA mutase</h4>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=27" title="Edit section: Methylmalonyl-CoA mutase">edit</a>]</div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Propionate_pathway.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Propionate_pathway.svg/400px-Propionate_pathway.svg.png" decoding="async" width="400" height="429" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Propionate_pathway.svg/600px-Propionate_pathway.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/e/e6/Propionate_pathway.svg/800px-Propionate_pathway.svg.png 2x" data-file-width="693" data-file-height="744" /></a><figcaption>Simplified schematic diagram of the propionate metabolic pathway. Methylmalonyl-CoA mutase requires the coenzyme adenosylcobalamin to convert L-methylmalonyl-CoA into succinyl-CoA. Otherwise, methylmalonic acid accumulates, making it a marker for vitamin B12 deficiency, among other things.</figcaption></figure> <a href="/wiki/Methylmalonyl-CoA_mutase" title="Methylmalonyl-CoA mutase">Methylmalonyl coenzyme A mutase</a> (MUT) is an isomerase enzyme which uses the AdoB12 form and reaction type 1 to convert <a href="/wiki/L-methylmalonyl-CoA" class="mw-redirect" title="L-methylmalonyl-CoA">L-methylmalonyl-CoA</a> to <a href="/wiki/Succinyl-CoA" title="Succinyl-CoA">succinyl-CoA</a>, an important step in the catabolic breakdown of some <a href="/wiki/Amino_acid" title="Amino acid">amino acids</a> into succinyl-CoA, which then enters energy production via the <a href="/wiki/Citric_acid_cycle" title="Citric acid cycle">citric acid cycle</a>.<a href="#cite_note-Takahashi2012-111">[111]</a> This functionality is lost in <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin B12 deficiency</a>, and can be measured clinically as an increased serum <a href="/wiki/Methylmalonic_acid" title="Methylmalonic acid">methylmalonic acid</a> (MMA) concentration. The MUT function is necessary for proper <a href="/wiki/Myelin" title="Myelin">myelin</a> synthesis.<a href="#cite_note-Calderon2020-4">[4]</a> Based on animal research, it is thought that the increased methylmalonyl-CoA hydrolyzes to form methylmalonate (methylmalonic acid), a neurotoxic dicarboxylic acid, causing neurological deterioration.<a href="#cite_note-Ballhausen2009-115">[115]</a> <div class="mw-heading mw-heading4"><h4 id="Methionine_synthase">Methionine synthase</h4>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=28" title="Edit section: Methionine synthase">edit</a>]</div> <figure class="skin-invert-image" typeof="mw:File/Thumb"><a href="/wiki/File:Folate_methionine_cycle.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Folate_methionine_cycle.svg/400px-Folate_methionine_cycle.svg.png" decoding="async" width="400" height="217" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Folate_methionine_cycle.svg/600px-Folate_methionine_cycle.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/5f/Folate_methionine_cycle.svg/800px-Folate_methionine_cycle.svg.png 2x" data-file-width="846" data-file-height="460" /></a><figcaption>Simplified schematic diagram of the folate methionine cycle. Methionine synthase transfers the methyl group to the vitamin and then transfers the methyl group to homocysteine, converting that to methionine.</figcaption></figure> <a href="/wiki/Methionine_synthase" title="Methionine synthase">Methionine synthase</a>, coded by MTR gene, is a methyltransferase enzyme which uses the MeB12 and reaction type 2 to transfer a methyl group from <a href="/wiki/5-methyltetrahydrofolate" class="mw-redirect" title="5-methyltetrahydrofolate">5-methyltetrahydrofolate</a> to <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a>, thereby generating <a href="/wiki/Tetrahydrofolate" class="mw-redirect" title="Tetrahydrofolate">tetrahydrofolate</a> (THF) and <a href="/wiki/Methionine" title="Methionine">methionine</a>.<a href="#cite_note-Froese2019-112">[112]</a> This functionality is lost in <a href="/wiki/Vitamin_B12_deficiency" title="Vitamin B12 deficiency">vitamin B12 deficiency</a>, resulting in an increased <a href="/wiki/Homocysteine" title="Homocysteine">homocysteine</a> level and the trapping of <a href="/wiki/Folate" title="Folate">folate</a> as 5-methyl-tetrahydrofolate, from which THF (the active form of folate) cannot be recovered. THF plays an important role in DNA synthesis, so reduced availability of THF results in ineffective production of cells with rapid turnover, in particular red blood cells, and also intestinal wall cells which are responsible for absorption. THF may be regenerated via MTR or may be obtained from fresh folate in the diet. Thus all of the DNA synthetic effects of B12 deficiency, including the <a href="/wiki/Megaloblastic_anemia" title="Megaloblastic anemia">megaloblastic anemia</a> of <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, resolve if sufficient dietary folate is present. Thus the best-known "function" of B12 (that which is involved with DNA synthesis, cell-division, and anemia) is actually a <a href="https://en.wiktionary.org/wiki/facultative" class="extiw" title="wikt:facultative">facultative</a> function which is mediated by B12-conservation of an active form of folate which is needed for efficient DNA production.<a href="#cite_note-Froese2019-112">[112]</a> Other cobalamin-requiring methyltransferase enzymes are also known in bacteria, such as Me-H4-MPT, coenzyme M methyltransferase.<a href="#cite_note-116">[116]</a> <div class="mw-heading mw-heading2"><h2 id="Physiology">Physiology</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=29" title="Edit section: Physiology">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Absorption">Absorption</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=30" title="Edit section: Absorption">edit</a>]</div> Vitamin B12 is absorbed by a B12-specific transport proteins or via passive diffusion.<a href="#cite_note-DRItext-12">[12]</a> Transport-mediated absorption and tissue delivery is a complex process involving three transport proteins: <a href="/wiki/Haptocorrin" title="Haptocorrin">haptocorrin</a> (HC), <a href="/wiki/Intrinsic_factor" title="Intrinsic factor">intrinsic factor</a> (IF) and <a href="/wiki/Transcobalamin_II" class="mw-redirect" title="Transcobalamin II">transcobalamin II</a> (TC2), and respective membrane receptor proteins. HC is present in saliva. As vitamin-containing food is digested by <a href="/wiki/Hydrochloric_acid" title="Hydrochloric acid">hydrochloric acid</a> and <a href="/wiki/Pepsin" title="Pepsin">pepsin</a> secreted into the stomach, HC binds the vitamin and protects it from acidic degradation.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Gueant-117">[117]</a> Upon leaving the stomach the hydrochloric acid of the <a href="/wiki/Chyme" title="Chyme">chyme</a> is neutralized in the <a href="/wiki/Duodenum" title="Duodenum">duodenum</a> by <a href="/wiki/Sodium_bicarbonate" title="Sodium bicarbonate">bicarbonate</a>,<a href="#cite_note-maton1993-118">[118]</a> and pancreatic proteases release the vitamin from HC, making it available to be bound by IF, which is a protein secreted by gastric <a href="/wiki/Parietal_cell" title="Parietal cell">parietal cells</a> in response to the presence of food in the stomach. IF delivers the vitamin to receptor proteins <a href="/wiki/Cubilin" title="Cubilin">cubilin</a> and <a href="/wiki/Amnionless" title="Amnionless">amnionless</a>, which together form the <a href="/wiki/Cubam" title="Cubam">cubam</a> receptor in the distal <a href="/wiki/Ileum" title="Ileum">ileum</a>. The receptor is specific to the IF-B12 complex, and so will not bind to any vitamin content that is not bound to IF.<a href="#cite_note-DRItext-12">[12]</a><a href="#cite_note-Gueant-117">[117]</a> Investigations into the intestinal absorption of B12 confirm that the upper limit of absorption per single oral dose is about 1.5 μg, with 50% efficiency. In contrast, the passive diffusion process of B12 absorption — normally a very small portion of total absorption of the vitamin from food consumption — may exceed the haptocorrin- and IF-mediated absorption when oral doses of B12 are very large, with roughly 1% efficiency. Thus, dietary supplement B12 supplementation at 500 to 1000 μg per day allows <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a> and certain other defects in B12 absorption to be treated with daily oral megadoses of B12 without any correction of the underlying absorption defects.<a href="#cite_note-Gueant-117">[117]</a> After the IF/B12 complex binds to cubam the complex is disassociated and the free vitamin is transported into the <a href="/wiki/Portal_circulation" class="mw-redirect" title="Portal circulation">portal circulation</a>. The vitamin is then transferred to TC2, which serves as the circulating plasma transporter, Hereditary defects in production of TC2 and its receptor may produce functional deficiencies in B12 and infantile <a href="/wiki/Megaloblastic_anemia" title="Megaloblastic anemia">megaloblastic anemia</a>, and abnormal B12 related biochemistry, even in some cases with normal blood B12 levels. For the vitamin to serve inside cells, the TC2-B12 complex must bind to a cell receptor protein and be <a href="/wiki/Endocytosis" title="Endocytosis">endocytosed</a>. TC2 is degraded within a <a href="/wiki/Lysosome" title="Lysosome">lysosome</a>, and free B12 is released into the cytoplasm, where it is transformed into the bioactive coenzyme by cellular enzymes.<a href="#cite_note-Gueant-117">[117]</a><a href="#cite_note-Seetharam2000-119">[119]</a> <div class="mw-heading mw-heading4"><h4 id="Malabsorption">Malabsorption</h4>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=31" title="Edit section: Malabsorption">edit</a>]</div> <a href="/wiki/Antacid" title="Antacid">Antacid</a> drugs that neutralize stomach acid and drugs that block acid production (such as <a href="/wiki/Proton-pump_inhibitor" title="Proton-pump inhibitor">proton-pump inhibitors</a>) will inhibit absorption of B12 by preventing release from food in the stomach.<a href="#cite_note-120">[120]</a> Other causes of B12 malabsorption include <a href="/wiki/Intrinsic_factor" title="Intrinsic factor">intrinsic factor</a> deficiency, <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, <a href="/wiki/Bariatric_surgery" title="Bariatric surgery">bariatric surgery</a> pancreatic insufficiency, obstructive jaundice, tropical sprue and celiac disease, and radiation enteritis of the distal ileum.<a href="#cite_note-Gueant-117">[117]</a> Age can be a factor. Elderly people are often <a href="/wiki/Achlorhydria" title="Achlorhydria">achlorhydric</a> due to reduced stomach parietal cell function, and thus have an increased risk of B12 deficiency.<a href="#cite_note-Baik-121">[121]</a> <div class="mw-heading mw-heading3"><h3 id="Storage_and_excretion">Storage and excretion</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=32" title="Edit section: Storage and excretion">edit</a>]</div> How fast B12 levels change depends on the balance between how much B12 is obtained from the diet, how much is secreted and how much is absorbed. The total amount of vitamin B12 stored in the body is about 2–5 mg in adults. Around 50% of this is stored in the liver. Approximately 0.1% of this is lost per day by secretions into the gut, as not all these secretions are reabsorbed. <a href="/wiki/Bile" title="Bile">Bile</a> is the main form of B12 excretion; most of the B12 secreted in the bile is recycled via <a href="/wiki/Enterohepatic_circulation" title="Enterohepatic circulation">enterohepatic circulation</a>. Excess B12 beyond the blood's binding capacity is typically excreted in urine. Owing to the extremely efficient enterohepatic circulation of B12, the liver can store 3 to 5 years' worth of vitamin B12; therefore, nutritional deficiency of this vitamin is rare in adults in the absence of malabsorption disorders.<a href="#cite_note-DRItext-12">[12]</a> In the absence of intrinsic factor or distal ileum receptors, only months to a year of vitamin B12 are stored.<a href="#cite_note-122">[122]</a> <div class="mw-heading mw-heading3"><h3 id="Cellular_reprogramming">Cellular reprogramming</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=33" title="Edit section: Cellular reprogramming">edit</a>]</div> Vitamin B12 through its involvement in one-carbon metabolism plays a key role in <a href="/wiki/Induced_pluripotent_stem_cell" title="Induced pluripotent stem cell">cellular reprogramming</a> and tissue regeneration and epigenetic regulation. Cellular reprogramming is the process by which somatic cells can be converted to a pluripotent state. Vitamin B12 levels affect the histone modification <a href="/wiki/H3K36me3" title="H3K36me3">H3K36me3</a>, which suppresses illegitimate transcription outside of <a href="/wiki/Promoter_(genetics)" title="Promoter (genetics)">gene promoters</a>. Mice undergoing in vivo reprogramming were found to become depleted in B12 and show signs of <a href="/wiki/Methionine" title="Methionine">methionine</a> starvation while supplementing reprogramming mice and cells with B12 increased reprogramming efficiency, indicating a cell-intrinsic effect.<a href="#cite_note-Kovatcheva_Melendez_Chondronasiou_Pietrocola_2023_p.-123">[123]</a><a href="#cite_note-Vílchez-Acost_2023-124">[124]</a> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=34" title="Edit section: Synthesis">edit</a>]</div> <div class="mw-heading mw-heading3"><h3 id="Biosynthesis">Biosynthesis</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=35" title="Edit section: Biosynthesis">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Cobalamin_biosynthesis" title="Cobalamin biosynthesis">Cobalamin biosynthesis</a></div> Vitamin B12 is derived from a <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrrolic structural framework</a> created by the enzymes <a href="/wiki/Porphobilinogen_deaminase" title="Porphobilinogen deaminase">deaminase</a> and <a href="/wiki/Uroporphyrinogen_III_synthase" title="Uroporphyrinogen III synthase">cosynthetase</a> which transform <a href="/wiki/Aminolevulinic_acid" title="Aminolevulinic acid">aminolevulinic acid</a> via <a href="/wiki/Porphobilinogen" title="Porphobilinogen">porphobilinogen</a> and <a href="/wiki/Hydroxymethylbilane" title="Hydroxymethylbilane">hydroxymethylbilane</a> to <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">uroporphyrinogen III</a>. The latter is the first <a href="/wiki/Macrocycle" title="Macrocycle">macrocyclic</a> intermediate common to <a href="/wiki/Heme" title="Heme">heme</a>, <a href="/wiki/Chlorophyll" title="Chlorophyll">chlorophyll</a>, <a href="/wiki/Siroheme" title="Siroheme">siroheme</a> and B12 itself.<a href="#cite_note-125">[125]</a><a href="#cite_note-126">[126]</a> Later steps, especially the incorporation of the additional methyl groups of its structure, were investigated using 13C <a href="/wiki/Isotopic_labelling" class="mw-redirect" title="Isotopic labelling">methyl-labelled</a> <a href="/wiki/S-adenosyl_methionine" class="mw-redirect" title="S-adenosyl methionine">S-adenosyl methionine</a>. It was not until a <a href="/wiki/Genetic_engineering" title="Genetic engineering">genetically engineered</a> strain of <a href="/wiki/Pseudomonas_denitrificans" title="Pseudomonas denitrificans">Pseudomonas denitrificans</a> was used, in which eight of the genes involved in the biosynthesis of the vitamin had been <a href="/wiki/Gene_expression" title="Gene expression">overexpressed</a>, that the complete sequence of <a href="/wiki/Methylation" title="Methylation">methylation</a> and other steps could be determined, thus fully establishing all the intermediates in the pathway.<a href="#cite_note-127">[127]</a><a href="#cite_note-128">[128]</a> Species from the following <a href="/wiki/Genus" title="Genus">genera</a> and the following individual species are known to synthesize B12: <a href="/wiki/Propionibacterium" title="Propionibacterium">Propionibacterium</a> shermanii, <a href="/wiki/Pseudomonas" title="Pseudomonas">Pseudomonas</a> denitrificans, <a href="/wiki/Streptomyces" title="Streptomyces">Streptomyces</a> griseus, <a href="/wiki/Acetobacterium" title="Acetobacterium">Acetobacterium</a>, <a href="/wiki/Aerobacter" class="mw-redirect" title="Aerobacter">Aerobacter</a>, <a href="/wiki/Agrobacterium" title="Agrobacterium">Agrobacterium</a>, <a href="/wiki/Alcaligenes" title="Alcaligenes">Alcaligenes</a>, <a href="/wiki/Azotobacter" title="Azotobacter">Azotobacter</a>, <a href="/wiki/Bacillus" title="Bacillus">Bacillus</a>, <a href="/wiki/Clostridium" title="Clostridium">Clostridium</a>, <a href="/wiki/Corynebacterium" title="Corynebacterium">Corynebacterium</a>, <a href="/wiki/Flavobacterium" title="Flavobacterium">Flavobacterium</a>, <a href="/wiki/Lactobacillus" title="Lactobacillus">Lactobacillus</a>, <a href="/wiki/Micromonospora" title="Micromonospora">Micromonospora</a>, <a href="/wiki/Mycobacterium" title="Mycobacterium">Mycobacterium</a>, <a href="/wiki/Nocardia" title="Nocardia">Nocardia</a>, <a href="/wiki/Proteus_(bacterium)" title="Proteus (bacterium)">Proteus</a>, <a href="/wiki/Rhizobium" title="Rhizobium">Rhizobium</a>, <a href="/wiki/Salmonella" title="Salmonella">Salmonella</a>, <a href="/wiki/Serratia" title="Serratia">Serratia</a>, <a href="/wiki/Streptococcus" title="Streptococcus">Streptococcus</a> and <a href="/wiki/Xanthomonas" title="Xanthomonas">Xanthomonas</a>.<a href="#cite_note-129">[129]</a><a href="#cite_note-130">[130]</a> <div class="mw-heading mw-heading3"><h3 id="Industrial">Industrial</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=36" title="Edit section: Industrial">edit</a>]</div> Industrial production of B12 is achieved through <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> of selected microorganisms.<a href="#cite_note-Fang2017-131">[131]</a> <a href="/wiki/Streptomyces_griseus" title="Streptomyces griseus">Streptomyces griseus</a>, a bacterium once thought to be a <a href="/wiki/Fungus" title="Fungus">fungus</a>, was the commercial source of vitamin B12 for many years.<a href="#cite_note-132">[132]</a> The species <a href="/wiki/Pseudomonas_denitrificans" title="Pseudomonas denitrificans">Pseudomonas denitrificans</a> and <a href="/wiki/Propionibacterium_freudenreichii" title="Propionibacterium freudenreichii">Propionibacterium freudenreichii</a> subsp. shermanii are more commonly used today.<a href="#cite_note-Fang2017-131">[131]</a> These are grown under special conditions to enhance yield. <a href="/wiki/Rhone-Poulenc" class="mw-redirect" title="Rhone-Poulenc">Rhone-Poulenc</a> improved yield via genetic engineering P. denitrificans.<a href="#cite_note-Piwowarek2018-133">[133]</a> <a href="/wiki/Propionibacterium" title="Propionibacterium">Propionibacterium</a>, the other commonly used bacteria, produce no <a href="/wiki/Exotoxin" title="Exotoxin">exotoxins</a> or <a href="/wiki/Endotoxin" class="mw-redirect" title="Endotoxin">endotoxins</a> and are generally recognized as safe (have been granted <a href="/wiki/GRAS" class="mw-redirect" title="GRAS">GRAS</a> status) by the <a href="/wiki/Food_and_Drug_Administration" title="Food and Drug Administration">Food and Drug Administration</a> of the United States.<a href="#cite_note-134">[134]</a> The total world production of vitamin B12 in 2008 was 35,000 kg (77,175 lb).<a href="#cite_note-135">[135]</a> <div class="mw-heading mw-heading3"><h3 id="Laboratory">Laboratory</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=37" title="Edit section: Laboratory">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Main article: <a href="/wiki/Vitamin_B12_total_synthesis" title="Vitamin B12 total synthesis">Vitamin B12 total synthesis</a></div> The complete laboratory <a href="/wiki/Vitamin_B12_total_synthesis" title="Vitamin B12 total synthesis">synthesis of B12</a> was achieved by <a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a><a href="#cite_note-136">[136]</a> and <a href="/wiki/Albert_Eschenmoser" title="Albert Eschenmoser">Albert Eschenmoser</a> in 1972.<a href="#cite_note-137">[137]</a><a href="#cite_note-Riether2003-138">[138]</a> The work required the effort of 91 postdoctoral fellows (mostly at Harvard) and 12 PhD students (at <a href="/wiki/ETH_Zurich" title="ETH Zurich">ETH Zurich</a>) from 19 nations. The synthesis constitutes a formal total synthesis, since the research groups only prepared the known intermediate cobyric acid, whose chemical conversion to vitamin B12 was previously reported. This synthesis of vitamin B12 is of no practical consequence due to its length, taking 72 chemical steps and giving an overall chemical yield well under 0.01%.<a href="#cite_note-RBWoodward-139">[139]</a> Although there have been sporadic synthetic efforts since 1972,<a href="#cite_note-Riether2003-138">[138]</a> the Eschenmoser–Woodward synthesis remains the only completed (formal) total synthesis. <div class="mw-heading mw-heading2"><h2 id="History">History</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=38" title="Edit section: History">edit</a>]</div> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236090951"><div role="note" class="hatnote navigation-not-searchable">Further information: <a href="/wiki/Vitamin#History" title="Vitamin">Vitamin § History</a></div> <div class="mw-heading mw-heading3"><h3 id="Descriptions_of_deficiency_effects">Descriptions of deficiency effects</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=39" title="Edit section: Descriptions of deficiency effects">edit</a>]</div> Between 1849 and 1887, <a href="/wiki/Thomas_Addison" title="Thomas Addison">Thomas Addison</a> described a case of <a href="/wiki/Pernicious_anemia" title="Pernicious anemia">pernicious anemia</a>, <a href="/wiki/William_Osler" title="William Osler">William Osler</a> and William Gardner first described a case of neuropathy, Hayem described large red cells in the peripheral blood in this condition, which he called "giant blood corpuscles" (now called <a href="/wiki/Macrocyte" class="mw-redirect" title="Macrocyte">macrocytes</a>), <a href="/wiki/Paul_Ehrlich" title="Paul Ehrlich">Paul Ehrlich</a> identified <a href="/wiki/Megaloblasts" class="mw-redirect" title="Megaloblasts">megaloblasts</a> in the bone marrow, and <a href="/wiki/Ludwig_Lichtheim" title="Ludwig Lichtheim">Ludwig Lichtheim</a> described a case of <a href="/wiki/Myelopathy" title="Myelopathy">myelopathy</a>.<a href="#cite_note-Wintrobe-140">[140]</a> <div class="mw-heading mw-heading3"><h3 id="Identification_of_liver_as_an_anti-anemia_food">Identification of liver as an anti-anemia food</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=40" title="Edit section: Identification of liver as an anti-anemia food">edit</a>]</div> During the 1920s, <a href="/wiki/George_Whipple" title="George Whipple">George Whipple</a> discovered that ingesting large amounts of raw <a href="/wiki/Liver" title="Liver">liver</a> seemed to most rapidly cure the anemia of blood loss in dogs, and hypothesized that eating liver might treat pernicious anemia.<a href="#cite_note-nobelprize-141">[141]</a> <a href="/wiki/Edwin_Cohn" class="mw-redirect" title="Edwin Cohn">Edwin Cohn</a> prepared a liver extract that was 50 to 100 times more potent in treating pernicious anemia than the natural liver products. <a href="/wiki/William_Bosworth_Castle" title="William Bosworth Castle">William Castle</a> demonstrated that gastric juice contained an "intrinsic factor" which when combined with meat ingestion resulted in absorption of the vitamin in this condition.<a href="#cite_note-Wintrobe-140">[140]</a> In 1934, George Whipple shared the 1934 <a href="/wiki/Nobel_Prize_in_Physiology_or_Medicine" title="Nobel Prize in Physiology or Medicine">Nobel Prize in Physiology or Medicine</a> with <a href="/wiki/William_P._Murphy" title="William P. Murphy">William P. Murphy</a> and <a href="/wiki/George_Minot" title="George Minot">George Minot</a> for discovery of an effective treatment for pernicious anemia using liver concentrate, later found to contain a large amount of vitamin B12.<a href="#cite_note-Wintrobe-140">[140]</a><a href="#cite_note-142">[142]</a> <div class="mw-heading mw-heading3"><h3 id="Identification_of_the_active_compound">Identification of the active compound</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=41" title="Edit section: Identification of the active compound">edit</a>]</div> While working at the Bureau of Dairy Industry, U.S. Department of Agriculture, <a href="/wiki/Mary_Shaw_Shorb" title="Mary Shaw Shorb">Mary Shaw Shorb</a> was assigned work on the bacterial strain Lactobacillus lactis Dorner (LLD), which was used to make yogurt and other cultured dairy products. The culture medium for LLD required liver extract. Shorb knew that the same liver extract was used to treat pernicious anemia (her father-in-law had died from the disease), and concluded that LLD could be developed as an assay method to identify the active compound. While at the University of Maryland she received a small grant from <a href="/wiki/Merck_%26_Co." title="Merck & Co.">Merck</a>, and in collaboration with <a href="/wiki/Karl_Folkers" class="mw-redirect" title="Karl Folkers">Karl Folkers</a> from that company, developed the LLD assay. This identified "LLD factor" as essential for the bacteria's growth.<a href="#cite_note-143">[143]</a> Shorb, Folker and <a href="/wiki/Alexander_R._Todd" class="mw-redirect" title="Alexander R. Todd">Alexander R. Todd</a>, at the <a href="/wiki/University_of_Cambridge" title="University of Cambridge">University of Cambridge</a>, used the LLD assay to extract the anti-pernicious anemia factor from liver extracts, purify it, and name it vitamin B12.<a href="#cite_note-ansc.umd.edu-144">[144]</a> In 1955, Todd helped elucidate the structure of the vitamin. The complete <a href="/wiki/Analytical_chemistry" title="Analytical chemistry">chemical structure</a> of the molecule was determined by <a href="/wiki/Dorothy_Hodgkin" title="Dorothy Hodgkin">Dorothy Hodgkin</a> based on <a href="/wiki/Crystallography" title="Crystallography">crystallographic</a> data and published in 1955<a href="#cite_note-145">[145]</a> and 1956,<a href="#cite_note-146">[146]</a> for which, and for other crystallographic analyses, she was awarded the Nobel Prize in Chemistry in 1964.<a href="#cite_note-frs-147">[147]</a> Hodgkin went on to decipher the structure of <a href="/wiki/Insulin" title="Insulin">insulin</a>.<a href="#cite_note-frs-147">[147]</a> George Whipple, George Minot and William Murphy were awarded the Nobel Prize in 1934 for their work on the vitamin. Three other Nobel laureates, Alexander R. Todd (1957), Dorothy Hodgkin (1964) and Robert Burns Woodward (1965) made important contributions to its study.<a href="#cite_note-148">[148]</a> <style data-mw-deduplicate="TemplateStyles:r1248256098">@media all and (max-width:720px){.mw-parser-output .mod-gallery{width:100%!important}}.mw-parser-output .mod-gallery{display:table}.mw-parser-output .mod-gallery-default{background:transparent;margin-top:4px}.mw-parser-output .mod-gallery-center{margin-left:auto;margin-right:auto}.mw-parser-output .mod-gallery-left{float:left}.mw-parser-output .mod-gallery-right{float:right}.mw-parser-output .mod-gallery-none{float:none}.mw-parser-output .mod-gallery-collapsible{width:100%}.mw-parser-output .mod-gallery .title,.mw-parser-output .mod-gallery .main,.mw-parser-output .mod-gallery .footer{display:table-row}.mw-parser-output .mod-gallery .title>div{display:table-cell;padding:0 4px 4px;text-align:center;font-weight:bold}.mw-parser-output .mod-gallery .main>div{display:table-cell}.mw-parser-output .mod-gallery .gallery{line-height:1.35em}.mw-parser-output .mod-gallery .footer>div{display:table-cell;padding:4px;text-align:right;font-size:85%;line-height:1em}.mw-parser-output .mod-gallery .title>div *,.mw-parser-output .mod-gallery .footer>div *{overflow:visible}.mw-parser-output .mod-gallery .gallerybox img{background:none!important}.mw-parser-output .mod-gallery .bordered-images .thumb img{border:solid var(--background-color-neutral,#eaecf0)1px}.mw-parser-output .mod-gallery .whitebg .thumb{background:var(--background-color-base,#fff)!important}</style><div class="mod-gallery mod-gallery-default mod-gallery-center"><div class="title"><div>Nobel laureates for discoveries relating to vitamin B12</div></div><div class="main"><div><ul class="gallery mw-gallery-traditional nochecker bordered-images whitebg"> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:George_Whipple_nobel.jpg" class="mw-file-description" title="George Whipple"><img alt="George Whipple" src="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/George_Whipple_nobel.jpg/120px-George_Whipple_nobel.jpg" decoding="async" width="120" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/95/George_Whipple_nobel.jpg/180px-George_Whipple_nobel.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/95/George_Whipple_nobel.jpg/240px-George_Whipple_nobel.jpg 2x" data-file-width="280" data-file-height="396" /></a></div> <div class="gallerytext"><a href="/wiki/George_Whipple" title="George Whipple">George Whipple</a></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:George_Minot_nobel.jpg" class="mw-file-description" title="George Minot"><img alt="George Minot" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/George_Minot_nobel.jpg/120px-George_Minot_nobel.jpg" decoding="async" width="120" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b0/George_Minot_nobel.jpg/180px-George_Minot_nobel.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b0/George_Minot_nobel.jpg/240px-George_Minot_nobel.jpg 2x" data-file-width="280" data-file-height="396" /></a></div> <div class="gallerytext"><a href="/wiki/George_Minot" title="George Minot">George Minot</a></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:William_P_Murphy.jpg" class="mw-file-description" title="William P. Murphy"><img alt="William P. Murphy" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/William_P_Murphy.jpg/125px-William_P_Murphy.jpg" decoding="async" width="125" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6c/William_P_Murphy.jpg/187px-William_P_Murphy.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/6/6c/William_P_Murphy.jpg 2x" data-file-width="220" data-file-height="300" /></a></div> <div class="gallerytext"><a href="/wiki/William_P._Murphy" title="William P. Murphy">William P. Murphy</a></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:Alexander_Todd_Nobel.jpg" class="mw-file-description" title="Alexander R. Todd"><img alt="Alexander R. Todd" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Alexander_Todd_Nobel.jpg/120px-Alexander_Todd_Nobel.jpg" decoding="async" width="120" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/59/Alexander_Todd_Nobel.jpg/180px-Alexander_Todd_Nobel.jpg 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/59/Alexander_Todd_Nobel.jpg/240px-Alexander_Todd_Nobel.jpg 2x" data-file-width="280" data-file-height="396" /></a></div> <div class="gallerytext"><a href="/wiki/Alexander_R._Todd" class="mw-redirect" title="Alexander R. Todd">Alexander R. Todd</a></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:Dorothy_Hodgkin_Nobel.jpg" class="mw-file-description" title="Dorothy Hodgkin"><img alt="Dorothy Hodgkin" src="//upload.wikimedia.org/wikipedia/en/thumb/3/3f/Dorothy_Hodgkin_Nobel.jpg/120px-Dorothy_Hodgkin_Nobel.jpg" decoding="async" width="120" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/3/3f/Dorothy_Hodgkin_Nobel.jpg/180px-Dorothy_Hodgkin_Nobel.jpg 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/3/3f/Dorothy_Hodgkin_Nobel.jpg/240px-Dorothy_Hodgkin_Nobel.jpg 2x" data-file-width="280" data-file-height="396" /></a></div> <div class="gallerytext"><a href="/wiki/Dorothy_Hodgkin" title="Dorothy Hodgkin">Dorothy Hodgkin</a></div> </li> <li class="gallerybox" style="width: 215px"> <div class="thumb" style="width: 210px; height: 200px;"><a href="/wiki/File:Robert_Woodward_Nobel.jpg" class="mw-file-description" title="Robert Burns Woodward"><img alt="Robert Burns Woodward" src="//upload.wikimedia.org/wikipedia/en/thumb/b/bf/Robert_Woodward_Nobel.jpg/120px-Robert_Woodward_Nobel.jpg" decoding="async" width="120" height="170" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/b/bf/Robert_Woodward_Nobel.jpg/180px-Robert_Woodward_Nobel.jpg 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/b/bf/Robert_Woodward_Nobel.jpg/240px-Robert_Woodward_Nobel.jpg 2x" data-file-width="280" data-file-height="396" /></a></div> <div class="gallerytext"><a href="/wiki/Robert_Burns_Woodward" title="Robert Burns Woodward">Robert Burns Woodward</a></div> </li> </ul></div></div></div> <div class="mw-heading mw-heading3"><h3 id="Commercial_production">Commercial production</h3>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=42" title="Edit section: Commercial production">edit</a>]</div> Industrial production of vitamin B12 is achieved through <a href="/wiki/Fermentation_(biochemistry)" class="mw-redirect" title="Fermentation (biochemistry)">fermentation</a> of selected microorganisms.<a href="#cite_note-Fang2017-131">[131]</a> As noted above, the completely synthetic laboratory synthesis of B12 was achieved by Robert Burns Woodward and Albert Eschenmoser in 1972, though this process has no commercial potential, requiring more than 70 steps and having a yield well below 0.01%.<a href="#cite_note-RBWoodward-139">[139]</a> <div class="mw-heading mw-heading2"><h2 id="Society_and_culture">Society and culture</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=43" title="Edit section: Society and culture">edit</a>]</div> In the 1970s, John A. Myers, a physician residing in Baltimore, developed a program of injecting vitamins and minerals intravenously for various medical conditions. The formula included 1000 μg of cyanocobalamin. This came to be known as the <a href="/wiki/Myers%27_cocktail" title="Myers' cocktail">Myers' cocktail</a>. After his death in 1984, other physicians and naturopaths took up prescribing "intravenous micro-nutrient therapy" with unsubstantiated health claims for treating fatigue, low energy, stress, anxiety, migraine, depression, immunocompromised, promoting weight loss and more.<a href="#cite_note-Gaby-149">[149]</a> However, other than a report on case studies<a href="#cite_note-Gaby-149">[149]</a> there are no benefits confirmed in the scientific literature.<a href="#cite_note-Gavura-150">[150]</a> Healthcare practitioners at clinics and spas prescribe versions of these intravenous combination products, but also intramuscular injections of just vitamin B12. A Mayo Clinic review concluded that there is no solid evidence that vitamin B12 injections provide an energy boost or aid weight loss.<a href="#cite_note-151">[151]</a> There is evidence that for elderly people, physicians often repeatedly prescribe and administer cyanocobalamin injections inappropriately, evidenced by the majority of subjects in one large study either having had normal serum concentrations or had not been tested prior to the injections.<a href="#cite_note-152">[152]</a> <div class="mw-heading mw-heading2"><h2 id="See_also">See also</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=44" title="Edit section: See also">edit</a>]</div> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cobalamin_biosynthesis" title="Cobalamin biosynthesis">Cobalamin biosynthesis</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li> <li><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a></li></ul> <div class="mw-heading mw-heading2"><h2 id="Further_reading">Further reading</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=45" title="Edit section: Further reading">edit</a>]</div> <ul><li><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 id="CITEREFGherasimLofgrenBanerjee2013" class="citation journal cs1">Gherasim C, Lofgren M, Banerjee R (May 2013). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3650358">"Navigating the B(12) road: assimilation, delivery, and disorders of cobalamin"</a>. J. Biol. Chem. 288 (19): 13186–13193. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1074%2Fjbc.R113.458810">10.1074/jbc.R113.458810</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3650358">3650358</a>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/23539619">23539619</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=J.+Biol.+Chem.&rft.atitle=Navigating+the+B%2812%29+road%3A+assimilation%2C+delivery%2C+and+disorders+of+cobalamin&rft.volume=288&rft.issue=19&rft.pages=13186-13193&rft.date=2013-05&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3650358%23id-name%3DPMC&rft_id=info%3Apmid%2F23539619&rft_id=info%3Adoi%2F10.1074%2Fjbc.R113.458810&rft.aulast=Gherasim&rft.aufirst=C&rft.au=Lofgren%2C+M&rft.au=Banerjee%2C+R&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC3650358&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+B12" class="Z3988"></li></ul> <div class="mw-heading mw-heading2"><h2 id="References">References</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=46" title="Edit section: References">edit</a>]</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-1"><a href="#cite_ref-1">^</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFPrietoNeuburgerSpinglerZelder2016" class="citation journal cs1">Prieto T, Neuburger M, Spingler B, Zelder F (2016). <a rel="nofollow" class="external text" href="http://www.zora.uzh.ch/133095/1/OL_2016_5292.pdf">"Inorganic Cyanide as Protecting Group in the Stereospecific Reconstitution of Vitamin B12 from an Artificial Green Secocorrinoid"</a> (PDF). <a href="/wiki/Organic_Letters" title="Organic Letters">Org. 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The Cochrane Database of Systematic Reviews. 1 (1): CD013823. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1002%2F14651858.CD013823.pub2">10.1002/14651858.CD013823.pub2</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> 10772977. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/38189492">38189492</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=The+Cochrane+Database+of+Systematic+Reviews&rft.atitle=Vitamin+B12+supplementation+during+pregnancy+for+maternal+and+child+health+outcomes&rft.volume=1&rft.issue=1&rft.pages=CD013823&rft.date=2024-01&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC10772977%23id-name%3DPMC&rft_id=info%3Apmid%2F38189492&rft_id=info%3Adoi%2F10.1002%2F14651858.CD013823.pub2&rft.aulast=Finkelstein&rft.aufirst=JL&rft.au=Fothergill%2C+A&rft.au=Venkatramanan%2C+S&rft.au=Layden%2C+AJ&rft.au=Williams%2C+JL&rft.au=Crider%2C+KS&rft.au=Qi%2C+YP&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+B12" class="Z3988"> </li> <li id="cite_note-PKIN2020VitB12-11">^ <a href="#cite_ref-PKIN2020VitB12_11-0">a</a> <a href="#cite_ref-PKIN2020VitB12_11-1">b</a> <link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222"><cite id="CITEREFStabler2020" class="citation book cs1">Stabler SP (2020). "Vitamin B12". In Marriott BP, Birt DF, Stallings VA, Yates AA (eds.). Present Knowledge in Nutrition, Eleventh Edition. London: Academic Press (Elsevier). pp. 257–272. <a href="/wiki/ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <a href="/wiki/Special:BookSources/978-0-323-66162-1" title="Special:BookSources/978-0-323-66162-1"><bdi>978-0-323-66162-1</bdi></a>. <q>US survey data from the NHANES What We Eat in America 2013e16 cohort reported the median vitamin B12 consumption for all adult men of 5.1 mcg and women of 3.5 mcg.95b Using the Estimated Average Requirement (EAR) for adults for Vitamin B12 of 2 mcg,93 less than 3% of men and 8% of women in the United States had inadequate diets using this comparator. 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title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=JAMA+Internal+Medicine&rft.atitle=Prevalence+of+Inappropriateness+of+Parenteral+Vitamin+B12+Administration+in+Ontario%2C+Canada&rft.volume=179&rft.issue=10&rft.pages=1434-1436&rft.date=2019-07&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6632124%23id-name%3DPMC&rft.issn=2168-6106&rft_id=info%3Apmid%2F31305876&rft_id=info%3Adoi%2F10.1001%2Fjamainternmed.2019.1859&rft.aulast=Silverstein&rft.aufirst=WK&rft.au=Lin%2C+Y&rft.au=Dharma%2C+C&rft.au=Croxford%2C+R&rft.au=Earle%2C+CC&rft.au=Cheung%2C+MC&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC6632124&rfr_id=info%3Asid%2Fen.wikipedia.org%3AVitamin+B12" class="Z3988"> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2>[<a href="/w/index.php?title=Vitamin_B12&action=edit&section=47" title="Edit section: External links">edit</a>]</div> <ul><li><a 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title="Special:EditPage/Template:Vitamins"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Vitamins_(A11)" style="font-size:114%;margin:0 4em"><a href="/wiki/Vitamin" title="Vitamin">Vitamins</a> (<a href="/wiki/ATC_code_A11" title="ATC code A11">A11</a>)</div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%">Fat soluble</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/Vitamin_A" title="Vitamin A">A</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/%CE%91-Carotene" title="Α-Carotene">α-Carotene</a></li> <li><a href="/wiki/%CE%92-Carotene" title="Β-Carotene">β-Carotene</a></li> <li><a href="/wiki/Retinol" title="Retinol">Retinol</a>#</li> <li><a href="/wiki/Tretinoin" title="Tretinoin">Tretinoin</a>#</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_D" title="Vitamin D">D</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>D2 <ul><li><a href="/wiki/Ergosterol" title="Ergosterol">Ergosterol</a></li> <li><a href="/wiki/Ergocalciferol" title="Ergocalciferol">Ergocalciferol</a>#</li></ul></li> <li>D3 <ul><li><a href="/wiki/7-Dehydrocholesterol" title="7-Dehydrocholesterol">7-Dehydrocholesterol</a></li> <li><a href="/wiki/Previtamin_D3" title="Previtamin D3">Previtamin D3</a></li> <li><a href="/wiki/Cholecalciferol" title="Cholecalciferol">Cholecalciferol</a>#</li> <li><a href="/wiki/Calcifediol" title="Calcifediol">25-hydroxycholecalciferol</a></li> <li><a href="/wiki/Calcitriol" title="Calcitriol">Calcitriol (1,25-dihydroxycholecalciferol)</a></li> <li><a href="/wiki/Calcitroic_acid" title="Calcitroic acid">Calcitroic acid</a></li></ul></li> <li>D4 <ul><li><a href="/wiki/22-Dihydroergocalciferol" title="22-Dihydroergocalciferol">Dihydroergocalciferol</a></li></ul></li> <li><a href="/wiki/Vitamin_D5" title="Vitamin D5">D5</a></li> <li>D analogues <ul><li><a href="/wiki/Alfacalcidol" title="Alfacalcidol">Alfacalcidol</a></li> <li><a href="/wiki/Dihydrotachysterol" title="Dihydrotachysterol">Dihydrotachysterol</a></li> <li><a href="/wiki/Calcipotriol" title="Calcipotriol">Calcipotriol</a></li> <li><a href="/wiki/Tacalcitol" title="Tacalcitol">Tacalcitol</a></li> <li><a href="/wiki/Paricalcitol" title="Paricalcitol">Paricalcitol</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_E" title="Vitamin E">E</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/Tocopherol" title="Tocopherol">Tocopherol</a> <ul><li><a href="/wiki/%CE%91-Tocopherol" title="Α-Tocopherol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocopherol" title="Β-Tocopherol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocopherol" title="Γ-Tocopherol">Gamma</a></li> <li><a href="/wiki/%CE%94-Tocopherol" title="Δ-Tocopherol">Delta</a></li></ul></li> <li><a href="/wiki/Tocotrienol" title="Tocotrienol">Tocotrienol</a> <ul><li><a href="/wiki/%CE%91-Tocotrienol" title="Α-Tocotrienol">Alpha</a></li> <li><a href="/wiki/%CE%92-Tocotrienol" title="Β-Tocotrienol">Beta</a></li> <li><a href="/wiki/%CE%93-Tocotrienol" title="Γ-Tocotrienol">Gamma</a></li> <li>Delta</li></ul></li> <li><a href="/wiki/Tocofersolan" title="Tocofersolan">Tocofersolan</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_K" title="Vitamin K">K</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/1,4-Naphthoquinone" title="1,4-Naphthoquinone">Naphthoquinone</a></li> <li><a href="/wiki/Phytomenadione" title="Phytomenadione">Phylloquinone (K1)</a>#</li> <li><a href="/wiki/Vitamin_K2" title="Vitamin K2">Menaquinones (K2)</a></li> <li><a href="/wiki/Menadione" title="Menadione">Menadione (K3)</a>‡</li> <li><a href="/wiki/Vitamin_K4" class="mw-redirect" title="Vitamin K4">Various (K4)</a></li> <li><a href="/wiki/4-Amino-2-methyl-1-naphthol" title="4-Amino-2-methyl-1-naphthol">4-Amino-2-methyl-1-naphthol (K5)</a>‡</li> <li><a href="/wiki/2-Methylnaphthalene-1,4-diamine" title="2-Methylnaphthalene-1,4-diamine">2-Methylnaphthalene-1,4-diamine (K6)</a></li> <li><a href="/wiki/4-Amino-3-methyl-1-naphthol" title="4-Amino-3-methyl-1-naphthol">4-Amino-3-methyl-1-naphthol (K7)</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Water soluble</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/B_vitamins" title="B vitamins">B</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>B1 <ul><li><a href="/wiki/Thiamine" title="Thiamine">Thiamine</a>#</li></ul></li> <li><a href="/wiki/Vitamin_B1_analogues" title="Vitamin B1 analogues">B1 analogues</a> <ul><li><a href="/wiki/Acefurtiamine" title="Acefurtiamine">Acefurtiamine</a></li> <li><a href="/wiki/Allithiamine" title="Allithiamine">Allithiamine</a></li> <li><a href="/wiki/Benfotiamine" title="Benfotiamine">Benfotiamine</a></li> <li><a href="/wiki/Fursultiamine" title="Fursultiamine">Fursultiamine</a></li> <li><a href="/wiki/Octotiamine" title="Octotiamine">Octotiamine</a></li> <li><a href="/wiki/Prosultiamine" title="Prosultiamine">Prosultiamine</a></li> <li><a href="/wiki/Sulbutiamine" title="Sulbutiamine">Sulbutiamine</a></li></ul></li> <li>B2 <ul><li><a href="/wiki/Riboflavin" title="Riboflavin">Riboflavin</a>#</li></ul></li> <li><a href="/wiki/Vitamin_B3" title="Vitamin B3">B3</a> <ul><li><a href="/wiki/Niacin" title="Niacin">Niacin</a></li> <li><a href="/wiki/Nicotinamide" title="Nicotinamide">Niacinamide</a>#</li></ul></li> <li>B5 <ul><li><a href="/wiki/Pantothenic_acid" title="Pantothenic acid">Pantothenic acid</a></li> <li><a href="/wiki/Panthenol" title="Panthenol">Dexpanthenol</a></li> <li><a href="/wiki/Pantethine" title="Pantethine">Pantethine</a></li></ul></li> <li><a href="/wiki/Vitamin_B6" title="Vitamin B6">B6</a> <ul><li><a href="/wiki/Pyridoxine" title="Pyridoxine">Pyridoxine</a>#, <a href="/wiki/Pyridoxal_phosphate" title="Pyridoxal phosphate">Pyridoxal phosphate</a></li> <li><a href="/wiki/Pyridoxamine" title="Pyridoxamine">Pyridoxamine</a></li> <li><a href="/wiki/Pyritinol" title="Pyritinol">Pyritinol</a></li></ul></li> <li>B7 <ul><li><a href="/wiki/Biotin" title="Biotin">Biotin</a></li></ul></li> <li>B9 <ul><li><a href="/wiki/Folate" title="Folate">Folic acid</a>#</li> <li><a href="/wiki/Dihydrofolic_acid" title="Dihydrofolic acid">Dihydrofolic acid</a></li> <li><a href="/wiki/Folinic_acid" title="Folinic acid">Folinic acid</a></li> <li><a href="/wiki/Levomefolic_acid" title="Levomefolic acid">Levomefolic acid</a></li></ul></li> <li><a class="mw-selflink selflink">B12</a> <ul><li><a href="/wiki/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Hydroxocobalamin" title="Hydroxocobalamin">Hydroxocobalamin</a>#</li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Vitamin_C" title="Vitamin C">C</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/Vitamin_C" title="Vitamin C">Ascorbic acid</a>#</li> <li><a href="/wiki/Dehydroascorbic_acid" title="Dehydroascorbic acid">Dehydroascorbic acid</a></li></ul> </div></td></tr></tbody></table><div></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/Multivitamin" title="Multivitamin">Multivitamins</a></li></ul> </div></td></tr><tr><td colspan="2" class="navbox-list navbox-even hlist" style="width:100%;padding:0"><div style="padding:0 0.25em"><div class="hlist"> <ul><li>#<a href="/wiki/WHO_Model_List_of_Essential_Medicines" title="WHO Model List of Essential Medicines">WHO-EM</a></li> <li>‡<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>†<a href="/wiki/Phases_of_clinical_research#Phase_III" title="Phases of clinical research">Phase III</a></li> <li>§Never to phase III</li></ul></li></ul> </div></div></td></tr></tbody></table></div> <div class="navbox-styles"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1129693374"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1236075235"></div><div role="navigation" class="navbox" aria-labelledby="Types_of_tetrapyrroles" 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"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1239400231"><div class="navbar plainlinks hlist navbar-mini"><ul><li class="nv-view"><a href="/wiki/Template:Tetrapyrroles" title="Template:Tetrapyrroles"><abbr title="View this template">v</abbr></a></li><li class="nv-talk"><a href="/wiki/Template_talk:Tetrapyrroles" title="Template talk:Tetrapyrroles"><abbr title="Discuss this template">t</abbr></a></li><li class="nv-edit"><a href="/wiki/Special:EditPage/Template:Tetrapyrroles" title="Special:EditPage/Template:Tetrapyrroles"><abbr title="Edit this template">e</abbr></a></li></ul></div><div id="Types_of_tetrapyrroles" style="font-size:114%;margin:0 4em">Types of <a href="/wiki/Tetrapyrrole" title="Tetrapyrrole">tetrapyrroles</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bilin_(biochemistry)" title="Bilin (biochemistry)">Bilanes</a> (Linear)</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><td colspan="2" class="navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Bilirubin" title="Bilirubin">Bilirubin</a></li> <li><a href="/wiki/Biliverdin" title="Biliverdin">Biliverdin</a></li> <li><a href="/wiki/Stercobilinogen" title="Stercobilinogen">Stercobilinogen</a></li> <li><a href="/wiki/Stercobilin" title="Stercobilin">Stercobilin</a></li> <li><a href="/wiki/Urobilinogen" title="Urobilinogen">Urobilinogen</a></li> <li><a href="/wiki/Urobilin" title="Urobilin">Urobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytobilin&action=edit&redlink=1" class="new" title="Phytobilin (page does not exist)">Phytobilins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><td colspan="2" class="navbox-list navbox-even" style="width:100%;padding:0"><div style="padding:0 0.25em"> <ul><li><a href="/wiki/Phytochromobilin" class="mw-redirect" title="Phytochromobilin">Phytochromobilin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Phycobilin" title="Phycobilin">Phycobilins</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/Phycoerythrobilin" title="Phycoerythrobilin">Phycoerythrobilin</a></li> <li><a href="/wiki/Phycocyanobilin" title="Phycocyanobilin">Phycocyanobilin</a></li> <li><a href="/wiki/Phycourobilin" title="Phycourobilin">Phycourobilin</a></li> <li><a href="/w/index.php?title=Phycoviolobilin&action=edit&redlink=1" class="new" title="Phycoviolobilin (page does not exist)">Phycoviolobilin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Macrocycle" title="Macrocycle">Macrocycle</a></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/Corrinoid" title="Corrinoid">Corrinoids</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/Adenosylcobalamin" title="Adenosylcobalamin">Adenosylcobalamin</a></li> <li><a href="/wiki/Cyanocobalamin" title="Cyanocobalamin">Cyanocobalamin</a></li> <li><a href="/wiki/Methylcobalamin" title="Methylcobalamin">Methylcobalamin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrin" title="Porphyrin">Porphyrins</a></th><td class="navbox-list-with-group navbox-list navbox-odd" 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/Protoporphyrin" class="mw-redirect" title="Protoporphyrin">Protoporphyrins</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/Heme" title="Heme">Heme</a> (<a href="/wiki/Heme_b" class="mw-redirect" title="Heme b">b</a>, <a href="/wiki/Heme_c" class="mw-redirect" title="Heme c">c</a>, <a href="/wiki/Heme_a" class="mw-redirect" title="Heme a">a</a>, <a href="/wiki/Heme_o" class="mw-redirect" title="Heme o">o</a>)</li> <li><a href="/w/index.php?title=Magnesium_protoporphyrin&action=edit&redlink=1" class="new" title="Magnesium protoporphyrin (page does not exist)">Magnesium protoporphyrin</a></li> <li><a href="/wiki/Protoporphyrin_IX" title="Protoporphyrin IX">Protoporphyrin IX</a></li> <li><a href="/wiki/Pterobilin" title="Pterobilin">Pterobilin</a></li> <li><a href="/wiki/Zinc_protoporphyrin" title="Zinc protoporphyrin">Zinc protoporphyrin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Phytoporphyrin&action=edit&redlink=1" class="new" title="Phytoporphyrin (page does not exist)">Phytoporphyrins</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/Chlorophyll_c" title="Chlorophyll c">Chlorophyll c</a></li> <li><a href="/wiki/Protochlorophyllide" title="Protochlorophyllide">Protochlorophyllide</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%">Reduced porphyrins</th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th id="Porphyrinogens" scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Porphyrinogen" title="Porphyrinogen">Porphyrinogens</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/Uroporphyrinogen" title="Uroporphyrinogen">Uroporphyrinogen</a> (<a href="/wiki/Uroporphyrinogen_I" title="Uroporphyrinogen I">I</a>, <a href="/wiki/Uroporphyrinogen_III" title="Uroporphyrinogen III">III</a>)</li> <li><a href="/wiki/Coproporphyrinogens" title="Coproporphyrinogens">Coproporphyrinogen</a> (<a href="/wiki/Coproporphyrinogen_I" title="Coproporphyrinogen I">I</a>, <a href="/wiki/Coproporphyrinogen_III" title="Coproporphyrinogen III">III</a>)</li> <li><a href="/wiki/Protoporphyrinogen_IX" title="Protoporphyrinogen IX">Protoporphyrinogen IX</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Chlorin" title="Chlorin">Chlorins</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/Chlorophyllide" title="Chlorophyllide">Chlorophyllide</a> (<a href="/wiki/Chlorophyllide_a" class="mw-redirect" title="Chlorophyllide a">a</a>, <a href="/wiki/Chlorophyllide_b" class="mw-redirect" title="Chlorophyllide b">b</a>)</li> <li><a href="/wiki/Chlorophyll" title="Chlorophyll">Chlorophyll</a> (<a href="/wiki/Chlorophyll_a" title="Chlorophyll a">a</a>, <a href="/wiki/Chlorophyll_b" title="Chlorophyll b">b</a>)</li> <li><a href="/wiki/Pheophytin" title="Pheophytin">Pheophytin</a> (<a href="/wiki/Pheophytin_a" class="mw-redirect" title="Pheophytin a">a</a>, <a href="/w/index.php?title=Pheophytin_b&action=edit&redlink=1" class="new" title="Pheophytin b (page does not exist)">b</a>)</li> <li><a href="/wiki/Bacteriochlorophyll_c" class="mw-redirect" title="Bacteriochlorophyll c">Bacteriochlorophyll c</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Bacteriochlorin" class="mw-redirect" title="Bacteriochlorin">Bacteriochlorins</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/Bacteriochlorophyll_a" class="mw-redirect" title="Bacteriochlorophyll a">Bacteriochlorophyll a</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/wiki/Isobacteriochlorin" class="mw-redirect" title="Isobacteriochlorin">Isobacteriochlorins</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/Siroheme" title="Siroheme">Siroheme</a></li> <li><a href="/wiki/Sirohydrochlorin" title="Sirohydrochlorin">Sirohydrochlorin</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%"><a href="/w/index.php?title=Corphin&action=edit&redlink=1" class="new" title="Corphin (page does not exist)">Corphins</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/Cofactor_F430" title="Cofactor F430">Cofactor F430</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr></tbody></table><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 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