Editing Adrenochrome (section)

== Chemistry ==
The oxidation reaction that converts [[adrenaline]] into adrenochrome occurs both ''[[in vivo]]'' and ''[[in vitro]]''. [[Silver oxide]] (Ag<sub>2</sub>O) was among the first reagents employed for this,<ref>{{cite journal |last1=Veer |first1=W. L. C. |title=Melanin and its precursors II. On adrenochrome |journal=Recueil des Travaux Chimiques des Pays-Bas |date=1942 |volume=61 |issue=9 |pages=638–646 |doi=10.1002/recl.19420610904}}</ref> but a variety of other oxidizing agents have been used successfully.<ref>{{cite journal |last1=Heacock |first1=R. A. |title=The Chemistry Of Adrenochrome And Related Compounds |journal=Chemical Reviews |date=1 April 1959 |volume=59 |issue=2 |pages=181–237 |doi=10.1021/cr50026a001 |url=https://chemistry.mdma.ch/hiveboard/rhodium/pdf/adrenochrome.review.pdf}}</ref> In solution, adrenochrome is pink and further oxidation of the compound causes it to polymerize into brown or black [[melanin]] compounds.<ref name="HofferOsmond1967" />

=== Synthesis ===
Adrenochrome is readily synthesized from commercially available reagents: [[chloroacetic acid]] and [[catechol]] react in the presence of [[phosphoryl chloride]] to yield chloroacetylcatechol. After purification, chloroacetylcatechol is reacted with aqueous [[methylamine]] and treated with [[hydrochloric acid]], yielding [[adrenalone]] [[hydrochloride]]. This is then [[hydrogenated]] to [[racemic]] [[adrenaline]]. Finally, adrenaline is oxidized to adrenochrome by an appropriate oxidizing agent such as [[silver oxide]].<ref name="schayer">{{cite journal|url=https://pubs.acs.org/doi/10.1021/ja01129a531|title=Synthesis of dl-Adrenalin-β-C14 and dl-Adrenochrome-β-C14|publisher=[[ACS Publications]]|author=Schayer, Richard W.|journal=Journal of the American Chemical Society |language=en-US|url-status=live|date=1952|volume=74 |issue=9 |page=2441 |doi=10.1021/ja01129a531 |bibcode=1952JAChS..74.2441S |access-date=October 25, 2022|archivedate=October 25, 2022|archiveurl=https://archive.today/20221025141335/https://pubs.acs.org/doi/10.1021/ja01129a531}}</ref>