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

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{About|the chemical compound|the conspiracy theory about Satanic child sacrifice|Adrenochrome conspiracy theory|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

| index_label = ([[racemic]])

| index1_label = (''R'')-Enantiomer

| index2_label = (''S'')-Enantiomer

| ChEMBL = 1314174

| ChEBI = 166544

| EINECS = 200-192-8

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

| CASNo = 54-06-8

| CASNo1 = 7506-92-5

| CASNo2 = 5181-82-8

| 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 = 3.785 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 [[semicarbazide]] [[derivative (chemistry)|derivative]], [[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 has a deep [[Violet (color)|violet]] coloration.<ref name=Aminochrome/>

== Chemistry ==

The oxidation reaction that converts [[adrenaline]] into adrenochrome occurs both ''[[in vivo]]'' and ''[[in vitro]]''. [[Silver oxide]] (Ag₂O) 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 oxidising 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="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 ==

[[File:Adrenochrome.jpg|thumb|left|An adrenochrome ampoule]]

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 name=Smythies>{{cite journal | last1 = Smythies | first1 = John | author-link1 = John Raymond Smythies | s2cid = 37594882 | title = The adrenochrome hypothesis of schizophrenia revisited | journal = [[Neurotoxicity Research]] | volume = 4 | issue = 2 | pages = 147–150 | date = January 2002 | pmid = 12829415 | doi = 10.1080/10298420290015827 | citeseerx = 10.1.1.688.3796 | issn = 1029-8428 | eissn = 1476-3524 | oclc = 50166444 }}</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 | last1 = Hoffer | first1 = Abram | author-link1 = Abram Hoffer | last2 = Osmond | first2 = Humphrey | author-link2 = Humphry Osmond | first3 = John | last3 = Smythies| author-link3 = John Raymond Smythies | title = Schizophrenia: A New Approach. II. Result of a Year's Research | journal = [[British Journal of Psychiatry|The Journal of Mental Science]] | volume = 100 | issue = 418 | pages = 29–45 | date = January 1954 | pmid = 13152519 | doi = 10.1192/bjp.100.418.29 | eissn = 1472-1465 | issn = 0007-1250 | lccn = 89649366 | oclc = 1537306 | s2cid = 42531852 | df = dmy-all }}</ref>

In what Hoffer called the "adrenochrome hypothesis",<ref name="Hoffer2">{{cite journal | last1 = Hoffer | first1 = Abram | author-link1 = Abram Hoffer | last2 = Osmond | first2 = Humphrey | author-link2 = Humphry Osmond | title = The Adrenochrome Hypothesis and Psychiatry | url = http://www.orthomolecular.org/library/jom/1999/articles/1999-v14n01-p049.shtml | access-date = 2024-03-15 | journal = [[The Journal of Orthomolecular Medicine]] | volume = 14 | issue = 1 | date = First Quarter 1999 | pages = 49–62 | archive-url = https://web.archive.org/web/20240220043758/http://www.orthomolecular.org/library/jom/1999/articles/1999-v14n01-p049.shtml | archive-date = 2024-02-20 | url-status = live | issn = 0834-4825 | oclc = 15726974 | s2cid = 41468628 | df = dmy-all}}</ref> he and Osmond in 1967 speculated that [[Megavitamin therapy|megadoses]] of [[vitamin C]] and [[niacin (nutrient)|niacin]] could cure schizophrenia by reducing brain adrenochrome.<ref name="hallucinogens">{{cite book | last1 = Hoffer | first1 = Abram | author-link1 = Abram Hoffer | last2 = Osmond | first2 = Humphrey | author-link2 = Humphry Osmond | date = 1968-01-01 | title = The Hallucinogens | url = https://archive.org/details/hallucinogens0000hoff/ | url-access = registration | language = en | edition = First | publisher = [[Academic Press]] | isbn = 978-0123518507 | lccn = 66030086 | oclc = 332437 | ol = OL35255701M | access-date = 2024-03-15 | via = [[Internet Archive]] | quote= | quote-page= | quote-pages= | df = dmy-all}}</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 web | 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 | access-date = 7 September 2020 | archive-date = 23 February 2021 | archive-url = https://web.archive.org/web/20210223194022/https://www.old.quackwatch.org/01QuackeryRelatedTopics/apa_megavitamin.pdf | url-status = dead }}</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.{{citation needed|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 name=Smythies /> 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>{{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>

Adrenochrome is also believed to have [[Cardiotoxicity|cardiotoxic]] properties.<ref>{{cite journal |last1=Bindoli |first1=Alberto |last2=Rigobello |first2=Maria Pia |last3=Galzigna |first3=Lauro |title=Toxicity of aminochromes |journal=Toxicology Letters |date=July 1989 |volume=48 |issue=1 |pages=3–20 |doi=10.1016/0378-4274(89)90180-X|pmid=2665188 |hdl=11577/2475305 |hdl-access=free }}</ref><ref>{{cite journal |last1=Behonick |first1=George S. |last2=Novak |first2=Mark J. |last3=Nealley |first3=Eric W. |last4=Baskin |first4=Steven I. |title=Toxicology update: the cardiotoxicity of the oxidative stress metabolites of catecholamines (aminochromes) |journal=Journal of Applied Toxicology |date=December 2001 |volume=21 |issue=S1 |pages=S15–S22 |doi=10.1002/jat.793|pmid=11920915 |s2cid=27865845 }}</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 [...]"<ref name=adams />

* [[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 |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."

* In the first episode of the ITV series ''[[Lewis (TV series)|Lewis]]'', "Whom the Gods Would Destroy", the motive for the crimes was that a prostitute had been killed years previously to harvest her adrenal glands.

* Adrenochrome is mentioned in the 2014 [[Warhammer 40,000]] novel [[List of Warhammer 40,000 novels#Chaos Space Marines|''The Talon of Horus'']] by Aaron Dembski-Bowden. It is described as a clear liquid beverage that is, "harvested from the adrenal glands of living slaves [...]"

* Adrenochrome is a subject of several [[Far-right subcultures|far right]] [[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|archive-date=20 September 2020|archive-url=https://web.archive.org/web/20200920020254/https://spectator.us/fear-adrenochrome-conspiracy-theory-drug/|url-status=dead}}</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|date=February 2019 |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> The theories commonly state that a cabal of [[Satanism|Satanists]] rape and murder children, and "harvest" adrenochrome from their victims' blood as a drug<ref>{{cite magazine|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|magazine=[[Wired (magazine)|Wired]]|date=July 31, 2020}}</ref><ref>{{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>{{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> In reality, adrenochrome has been produced by [[organic synthesis]] since at least 1952,<ref>{{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 |access-date=October 25, 2022|archivedate=October 25, 2022|archiveurl=https://archive.today/20221025141335/https://pubs.acs.org/doi/10.1021/ja01129a531}}</ref><ref>{{cite web|url=https://patents.google.com/patent/US3445478A/en|title=Method of synthesizing adrenochrome monoaminoguanidine|publisher=[[Google Patents]]|language=en-US|url-status=live|date=1965|access-date=October 25, 2022|archivedate=October 16, 2021|archiveurl=https://web.archive.org/web/20211016150832/https://patents.google.com/patent/US3445478A/en}}</ref> is synthesized by [[biotechnology]] companies for research purposes, and has no medical or recreational uses.<ref>{{cite web|url=https://science.howstuffworks.com/adrenochrome.htm|title=Untangling the Medical Misinformation Around Adrenochrome|author=Walker-Journey, Jennifer|publisher=[[HowStuffWorks]]|language=en-US|url-status=live|date=April 14, 2021|access-date=October 25, 2022|archivedate=April 14, 2021|archiveurl=https://web.archive.org/web/20210414211128/https://science.howstuffworks.com/adrenochrome.htm}}</ref>

== References ==

{{reflist}}

== External links ==

*Joe Schwarcz PhD [https://www.mcgill.ca/oss/article/pseudoscience/qanons-adrenochrome-quackery QAnon’s Adrenochrome Quackery] 10 Feb 2022 Office for Science and Society, [[McGill University]]

* [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:Indolequinones]]

[[Category:Secondary alcohols]]