Editing Naloxone (section)

==Chemistry==
Naloxone, also known as N-allylnoroxymorphone or as 17-allyl-4,5α-epoxy-3,14-dihydroxymorphinan-6-one, is a [[synthetic compound|synthetic]] [[morphinan]] [[chemical derivative|derivative]] and was derived from [[oxymorphone]] (14-hydroxydihydromorphinone), an opioid analgesic.<ref name="DeanBilsky2009">{{cite book| vauthors = Dean R, Bilsky EJ, Negus SS |title=Opiate Receptors and Antagonists: From Bench to Clinic|url=https://books.google.com/books?id=zqj2vy6VFUcC&pg=PA514|date=12 March 2009|publisher=Springer Science & Business Media|isbn=978-1-59745-197-0|pages=514–}}</ref><ref name="Nagase2011">{{cite book| vauthors = Nagase H |title=Chemistry of Opioids|url=https://books.google.com/books?id=eegLBwAAQBAJ&pg=PA93|date=21 January 2011|publisher=Springer|isbn=978-3-642-18107-8|pages=93–}}</ref><ref name="NIST">{{cite web | url=http://webbook.nist.gov/cgi/cbook.cgi?ID=C465656 | title=Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5α)- | access-date=20 November 2017 | archive-date=1 December 2017 | archive-url=https://web.archive.org/web/20171201041953/http://webbook.nist.gov/cgi/cbook.cgi?ID=C465656 | url-status=live }}</ref> Oxymorphone, in turn, was derived from [[morphine]], an opioid analgesic and [[natural product|naturally occurring]] constituent of the [[opium poppy]].<ref name="SeppalaRose2011">{{cite book|vauthors=Seppala MD, Rose ME|title=Prescription Painkillers: History, Pharmacology, and Treatment|url=https://books.google.com/books?id=HkXXDQAAQBAJ&pg=PT143|date=25 January 2011|publisher=Hazelden Publishing|isbn=978-1-59285-993-1|pages=143–|access-date=20 November 2017|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020758/https://books.google.com/books?id=HkXXDQAAQBAJ&pg=PT143|url-status=live}}</ref> Naloxone is a [[racemic mixture]] of two [[enantiomer]]s, (–)-naloxone (levonaloxone) and [[(+)-naloxone]] (dextronaloxone), only the former of which is active at opioid receptors.<ref name="Bennett2006">{{cite book|vauthors=Bennett LA|title=New Topics in Substance Abuse Treatment|url=https://books.google.com/books?id=aIDGy72xseMC&pg=PA9|year=2006|publisher=Nova Publishers|isbn=978-1-59454-831-4|pages=9–|access-date=20 November 2017|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020758/https://books.google.com/books?id=aIDGy72xseMC&pg=PA9|url-status=live}}</ref><ref name="Wang2003">{{cite book|vauthors=Wang JQ|title=Drugs of Abuse: Neurological Reviews and Protocols|url=https://books.google.com/books?id=cuxYNGtzSTIC&pg=PA44|year=2003|publisher=Springer Science & Business Media|isbn=978-1-59259-358-3|pages=44–|access-date=20 November 2017|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020759/https://books.google.com/books?id=cuxYNGtzSTIC&pg=PA44|url-status=live}}</ref> The drug is highly [[lipophilic]], allowing it to rapidly penetrate the brain and to achieve a far greater brain to serum ratio than that of morphine.<ref name="DeanBilsky2009"/> Opioid antagonists related to naloxone include [[cyprodime]], [[nalmefene]], [[nalodeine]], [[naloxol]], and [[naltrexone]].<ref name="BruntonChabner2010">{{cite book|vauthors=Brunton L, Chabner B, Knollman B|title=Goodman and Gilman's The Pharmacological Basis of Therapeutics, Twelfth Edition|url=https://books.google.com/books?id=bVUfAQAAQBAJ|date=20 December 2010|publisher=McGraw Hill Professional|isbn=978-0-07-162442-8|page=510|access-date=20 November 2017|archive-date=13 January 2023|archive-url=https://web.archive.org/web/20230113020759/https://books.google.com/books?id=bVUfAQAAQBAJ|url-status=live}}</ref>