Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Adrenochrome: Difference between pages

{{Short description|Chemical compound}}

{{For|the Sisters of Mercy song|Some Girls Wander by Mistake}}

{{Use dmy dates|date=January 2022}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477243063

| ImageSize = 170

| ImageAlt = Structural formula of adrenochrome

| ImageFile1 = Adrenochrome 3D ball.png

| ImageSize1 = 170

| ImageAlt1 = Ball-and-stick model of the adrenochrome molecule

| IUPACName = 3-Hydroxy-1-methyl-2,3-dihydro-1''H''-indole-5,6-dione

| OtherNames = Adraxone; Pink adrenaline

| ChEMBL = 1314174

| ChEBI = 166544

| EINECS = 200-192-8

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 54-06-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 70G54NQL71

| Appearance = deep-violet<ref name=Aminochrome>{{cite journal |last1=Heacock |first1=R. A. |last2=Nerenberg |first2=C. |last3=Payza |first3=A. N. |title=The Chemistry of the "Aminochromes": Part I. The Preparation and Paper Chromatography of Pure Adrenochrome |journal=Canadian Journal of Chemistry |date=1 May 1958 |volume=36 |issue=5 |pages=853–857 |doi=10.1139/v58-124 |doi-access=free }}</ref>

| Density = 3.264 g/cm³

| BoilingPtC = 115-120

| BoilingPt_notes = (decomposes)

'''Adrenochrome''' is a [[chemical compound]] produced by the [[organic oxidation reaction|oxidation]] of [[adrenaline]] ([[epinephrine]]). It was the subject of limited research from the 1950s through to the 1970s as a potential cause of [[schizophrenia]]. While it has no current medical application, the related [[derivative (chemistry)|derivative]] compound, [[carbazochrome]], is a [[hemostatic]] medication. Despite this compound's name, it is unrelated to the element [[chromium]]; instead, the [[wiktionary:-chrome|‑chrome]] suffix indicates a relationship to color, as pure adrenochrome is deep [[Violet (color)|violet]].<ref name=Aminochrome/>

== Chemistry ==

The oxidation reaction that converts adrenaline into adrenochrome occurs both ''[[in vivo]]'' and ''[[in vitro]]''. ''In vitro'', [[silver oxide]] (Ag₂O) is used.<ref>MacCarthy, Chim, Ind. Paris 55,435(1946)</ref> In solution, adrenochrome is pink and further oxidation of the compound causes it to polymerize into brown or black [[melanin]] compounds.<ref name="HofferOsmond2013">{{cite book|author1=A. Hoffer|author2=H. Osmond|title=The Hallucinogens|url=https://books.google.com/books?id=nBMlBQAAQBAJ&pg=PA272|date=22 October 2013|publisher=Elsevier|isbn=978-1-4832-6169-0|pages=272–273}}</ref>

== History ==

Several small-scale studies (involving 15 or fewer test subjects) conducted in the 1950s and 1960s reported that adrenochrome triggered [[psychotic]] reactions such as [[thought disorder]] and [[derealization]].<ref>{{cite journal | vauthors = Smythies J | s2cid = 37594882 | title = The adrenochrome hypothesis of schizophrenia revisited | journal = [[Neurotoxicity Research]] | volume = 4 | issue = 2 | pages = 147–150 | date = March 2002 | pmid = 12829415 | doi = 10.1080/10298420290015827 | citeseerx = 10.1.1.688.3796 }}</ref>

In 1954, researchers [[Abram Hoffer]] and [[Humphry Osmond]] claimed that adrenochrome is a [[neurotoxin|neurotoxic]], [[psychotomimetic]] substance and may play a role in [[schizophrenia]] and other mental illnesses.<ref name="pmid13152519">{{cite journal | vauthors = Hoffer A, Osmond H, Smithies J | title = Schizophrenia; a new approach. II. Result of a year's research | journal = The Journal of Mental Science | volume = 100 | issue = 418 | pages = 29–45 | date = January 1954 | pmid = 13152519 | doi = 10.1192/bjp.100.418.29}}</ref>

In what Hoffer called the "adrenochrome hypothesis",<ref name="Hoffer2">{{cite journal | vauthors = Hoffer A | title = The Adrenochrome Hypothesis and Psychiatry | journal = The Journal of Orthomolecular Medicine | volume = 14 | issue = 1 | year = 1999 | pages = 49–62 | url = http://www.orthomolecular.org/library/jom/1999/articles/1999-v14n01-p049.shtml }}</ref> he and Osmond in 1967 speculated that [[Megavitamin therapy|megadoses]] of [[vitamin C]] and [[niacin]] could cure schizophrenia by reducing brain adrenochrome.<ref name="hallucinogens">{{cite book| vauthors = Hoffer A, Osmond H | title = The Hallucinogens | publisher = Academic Press | date = 1967 |isbn=978-1-4832-6169-0 }}</ref><ref name=hoffer94>{{cite journal | vauthors = Hoffer A | date = 1994 | title = Schizophrenia: An Evolutionary Defense Against Severe Stress | journal = Journal of Orthomolecular Medicine | volume = 9 | issue = 4 | pages = 205–2221 | url = http://orthomolecular.org/library/jom/1994/pdf/1994-v09n04-p205.pdf }}</ref>

The treatment of schizophrenia with such potent anti-oxidants is highly contested. In 1973, the [[American Psychiatric Association]] reported methodological flaws in Hoffer's work on niacin as a schizophrenia treatment and referred to follow-up studies that did not confirm any benefits of the treatment.<ref name="APA">{{Cite journal | vauthors = Lipton MA, Ban TA, Kane FJ, Levine J, Mosher LR, Wittenborn R | title = Task Force Report on Megavitamin and Orthomolecular Therapy in Psychiatry | publisher = American Psychiatric Association | year = 1973 | url = https://www.old.quackwatch.org/01QuackeryRelatedTopics/apa_megavitamin.pdf }}</ref> Multiple additional studies in the United States,<ref name="ArchGenPsy">{{cite journal | doi = 10.1001/archpsyc.1973.01750330010002 |vauthors=Wittenborn JR, Weber ES, Brown M | title = Niacin in the Long-Term Treatment of Schizophrenia | journal = Archives of General Psychiatry | year = 1973 | volume = 28 | issue = 3 | pages = 308–315 | pmid = 4569673 | url = http://archpsyc.ama-assn.org/cgi/content/abstract/28/3/308}}</ref> Canada,<ref name="SZ Bull">{{cite journal | vauthors = Ban TA, Lehmann HE | title = Nicotinic Acid in the Treatment of Schizophrenia: A Summary Report | journal = Schizophrenia Bulletin | year = 1970 | volume = 1 | issue = 3 | pages = 5–7 | doi = 10.1093/schbul/1.3.5 | doi-access = free }}</ref> and Australia<ref name="ANZJP">{{cite journal |vauthors=Vaughan K, McConaghy N | s2cid = 38857700 | title = Megavitamin and dietary treatment in schizophrenia: a randomised, controlled trial | journal = Australian and New Zealand Journal of Psychiatry | year = 1999 | volume = 33 | issue = 1 | pages = 84–88 | pmid = 10197889 | doi =10.1046/j.1440-1614.1999.00527.x}}</ref> similarly failed to find benefits of megavitamin therapy to treat [[History of schizophrenia|schizophrenia]].

The adrenochrome theory of schizophrenia waned, despite some evidence that it may be [[psychotomimetic]], as adrenochrome was not detectable in people with schizophrenia.{{cn|date=March 2021}}

In the early 2000s, interest was renewed by the discovery that adrenochrome may be produced normally as an intermediate in the formation of [[neuromelanin]].<ref>{{Cite journal|last=Smythies|first=John|date=2002|title=The adrenochrome hypothesis of schizophrenia revisited|url=https://link.springer.com/article/10.1080%2F10298420290015827|journal=Neurotoxicity Research|language=en|volume=4|issue=2|pages=147–150|doi=10.1080/10298420290015827|pmid=12829415|s2cid=37594882|issn=1029-8428}}</ref> This finding may be significant because adrenochrome is detoxified at least partially by [[glutathione-S-transferase]]. Some studies have found genetic defects in the gene for this enzyme.<ref name="Smythies">{{cite book | vauthors = Smythies J | veditors = Smythies J |title=Disorders of Synaptic Plasticity and Schizophrenia |date=2004 |publisher=Elsevier Academic Press |isbn=978-0-12-366860-8 |pages=xv |edition=1st}}</ref>

== In popular culture ==

* In his 1954 book ''[[The Doors of Perception]]'', [[Aldous Huxley]] mentioned the discovery and the alleged effects of adrenochrome which he likened to the symptoms of [[mescaline]] intoxication, although he had never consumed it.<ref name=adams />

* [[Anthony Burgess]] mentions adrenochrome as "drencrom" at the beginning of his 1962 novel ''[[A Clockwork Orange (novel)|A Clockwork Orange]]''. The protagonist and his friends are drinking drug-laced milk: "They had no license for selling liquor, but there was no law yet against prodding some of the new veshches which they used to put into the old moloko, so you could peet it with vellocet or synthemesc or drencrom or one or two other veshches [...]"

* [[Hunter S. Thompson]] mentioned adrenochrome in his 1971 book ''[[Fear and Loathing in Las Vegas]]''.<ref name="friedberg">{{cite magazine | last=Friedberg | first=Brian | title=The Dark Virality of a Hollywood Blood-Harvesting Conspiracy | magazine=Wired | url=https://www.wired.com/story/opinion-the-dark-virality-of-a-hollywood-blood-harvesting-conspiracy/ | access-date=21 February 2021}}</ref> This is the likely origin of current myths surrounding this compound, because a character states that "There's only one source for this stuff{{nbsp}}... the adrenaline glands from a living human body. It's no good if you get it out of a corpse." The adrenochrome scene also appears in the novel's [[Fear and Loathing in Las Vegas (film)|film adaptation]].<ref name=adams>{{cite news |last1=Adams |first1=Josie | name-list-style = vanc |title=The truth about adrenochrome |url=https://thespinoff.co.nz/society/07-04-2020/explainer-adrenochrome-the-drug-that-doesnt-exist/ |access-date=28 June 2020 |work=The Spinoff |date=7 April 2020}}</ref> In the DVD commentary, director [[Terry Gilliam]] admits that his and Thompson's portrayal is a fictional exaggeration. Gilliam insists that the [[Psychoactive drug|drug]] is entirely fictional and seems unaware of the existence of a substance with the same name. Hunter S. Thompson also mentions adrenochrome in his book ''[[Fear and Loathing on the Campaign Trail '72]]''. In the footnotes in chapter April, page 140 he says, "It was sometime after midnight in a ratty hotel room and my memory of the conversation is hazy, due to massive ingestion of booze, [[fatback]], and forty [[Cubic_centimetre|cc]]'s of adrenochrome."

* The harvesting of an adrenal gland from a live victim to obtain adrenochrome for [[Substance abuse|drug abuse]] is a plot feature in the [[List of Lewis episodes|second episode]] of the television series ''[[Lewis (TV series)|Lewis]]'' (2007).

* The harvest of adrenochrome from murder victims is a key part of the 2017 horror film ''Adrenochrome''.<ref>{{cite web |url=https://www.imdb.com/title/tt2273648/ |title=Adrenochrome (2017)|website=[[IMDb]]}}</ref>

* Adrenochrome is a component of several [[conspiracy theories]] such as [[QAnon]] and [[Pizzagate conspiracy theory|Pizzagate]],<ref>{{Cite web|title=Fear and adrenochrome|url=https://spectator.us/fear-adrenochrome-conspiracy-theory-drug/|date=4 May 2020|website=Spectator USA|language=en-US|access-date=23 May 2020}}</ref><ref>{{Cite web|title=How Facebook connects 'pizzagate' conspiracy theorists|url=https://www.nbcnews.com/tech/social-media/fire-pizzagate-shop-reignites-conspiracy-theorists-who-find-home-facebook-n965956|website=NBC News|language=en|access-date=23 May 2020}}</ref><ref>{{Skeptoid | id=4750 | number=750 | title=How to Extract Adrenochrome from Children | date=20 October 2020 | access-date=20 October 2020}}</ref> with the chemical helping the theories play a similar role to earlier [[blood libel]] and [[satanic ritual abuse]] stories.<ref name="kantrowitz1">{{cite magazine |last1=Kantrowitz |first1=Lia |title=QAnon, Blood Libel, and the Satanic Panic |url=https://newrepublic.com/article/159529/qanon-blood-libel-satanic-panic |magazine=The New Republic |access-date=8 May 2021 |date=29 September 2020}}</ref> According to QAnon, which has incorporated and expanded Pizzagate's claims about child sex abuse rings, a cabal of [[Satanism|Satanists]] rapes and murders children, using the adrenochrome they "harvest" from their victims' blood as a drug<ref>{{cite news |last1=Friedberg |first1=Brian |title=The Dark Virality of a Hollywood Blood-Harvesting Conspiracy |url=https://www.wired.com/story/opinion-the-dark-virality-of-a-hollywood-blood-harvesting-conspiracy/ |access-date=February 16, 2022 |work=Wired.com |date=July 31, 2020}}</ref><ref name="adrenochrome">{{cite news |last1=Hitt |first1=Tarpley |title=How QAnon Became Obsessed With 'Adrenochrome,' an Imaginary Drug Hollywood Is 'Harvesting' from Kids |url=https://www.thedailybeast.com/how-qanon-became-obsessed-with-adrenochrome-an-imaginary-drug-hollywood-is-harvesting-from-kids |newspaper=The Daily Beast |access-date=27 January 2021 |date=August 14, 2020}}</ref> or as an [[Elixir of life|elixir of youth]].<ref name="glossary">{{cite news |date= January 21, 2021|title=QAnon: A Glossary |work=[[Anti-Defamation League]] |url=https://www.adl.org/blog/qanon-a-glossary |access-date=February 15, 2022}}</ref>

== References ==

{{reflist}}

== External links ==

* [http://www.erowid.org/chemicals/adrenochrome/adrenochrome_info1.shtml Adrenochrome Commentary] at erowid.org

* [https://web.archive.org/web/20090111090507/http://webeye.ophth.uiowa.edu/eyeforum/atlassearch1.htm?ComparisonType1_1=LIKE&Value1_1=adrenochrome&FieldName1=Diagnosis&NumCriteriaDetails1=1&PageID=2&GlobalOperator=AND&NumCriteria=1 Adrenochrome deposits] resulting from the use of epinephrine-containing eye drops used to treat glaucoma from the [https://web.archive.org/web/20050303205443/http://webeye.ophth.uiowa.edu/eyeforum/atlassearch1.htm Iowa Eye Atlas] (searched for diagnosis = adrenochrome)

[[Category:Secondary alcohols]]

[[Category:Indolequinones]]