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Adrenochrome

From Wikipedia, the free encyclopedia
Chemical compound

This article is about the chemical compound. For the Sisters of Mercy song, seeSome Girls Wander by Mistake.

Adrenochrome
Structural formula of adrenochrome
Ball-and-stick model of the adrenochrome molecule
Names
IUPAC name
3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione
Other names
Adraxone; Pink adrenaline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.000.176Edit this at Wikidata
EC Number
UNII
  • InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3 checkY
    Key: RPHLQSHHTJORHI-UHFFFAOYSA-N checkY
  • (racemic): InChI=1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
    Key: RPHLQSHHTJORHI-UHFFFAOYAD
  • (racemic): O=C1\C=C2/C(=C\C1=O)N(CC2O)C
Properties
C9H9NO3
Molar mass179.175 g·mol−1
Appearancedeep-violet[1]
Density3.785 g/cm3
Boiling point115–120 °C (239–248 °F; 388–393 K) (decomposes)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Adrenochrome is achemical compound produced by theoxidation ofadrenaline (epinephrine). It was the subject of limited research from the 1950s through to the 1970s as a potential cause ofschizophrenia. While adrenochrome has no currently proven medical application, thesemicarbazidederivative,carbazochrome, is ahemostatic medication. Adrenochrome is mass produced and commercially available to the public, and is not acontrolled substance.[2][3]

Despite this compound's name, it is unrelated to the elementchromium; instead, the "chrome" suffix indicates a relationship to color, as pure adrenochrome has a deepviolet color.[1]

Chemistry

[edit]

The oxidation reaction that convertsadrenaline into adrenochrome occurs bothin vivo andin vitro.Silver oxide (Ag2O) was among the first reagents employed for this,[4] but a variety of other oxidizing agents have been used successfully.[5] In solution, adrenochrome is pink and further oxidation of the compound causes it to polymerize into brown or blackmelanin compounds.[6]

Synthesis

[edit]

Adrenochrome is readily synthesized from commercially available reagents:chloroacetic acid andcatechol react in the presence ofphosphoryl chloride to yield chloroacetylcatechol. After purification, chloroacetylcatechol is reacted with aqueousmethylamine and treated withhydrochloric acid, yieldingadrenalonehydrochloride. This is thenhydrogenated toracemicadrenaline. Finally, adrenaline is oxidized to adrenochrome by an appropriate oxidizing agent such assilver oxide.[7]

History

[edit]
An adrenochrome ampoule

Several small-scale studies involving 15 or fewer test subjects conducted in the 1950s and 1960s reported that adrenochrome triggeredpsychotic reactions such asthought disorder andderealization.[8]

In 1954, researchersAbram Hoffer andHumphry Osmond claimed that adrenochrome is aneurotoxic,psychotomimetic substance and may play a role inschizophrenia and other mental illnesses.[9] In what Hoffer called the "adrenochrome hypothesis",[10] he and Osmond in 1967 speculated thatmegadoses ofvitamin C andniacin could cure schizophrenia by reducing brain adrenochrome.[6][11]

The treatment of schizophrenia with such potent anti-oxidants is controversial. In 1973, theAmerican 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.[12] Multiple additional studies in the United States,[13] Canada,[14] and Australia[15] similarly failed to find benefits of megavitamin therapy to treatschizophrenia.

The adrenochrome theory of schizophrenia waned, despite some evidence that it may bepsychotomimetic, as adrenochrome was not detectable in people with schizophrenia.[citation needed]

In the early 2000s, interest was renewed by the discovery that adrenochrome may be produced normally as an intermediate in the formation ofneuromelanin.[8] This finding may be significant because adrenochrome is detoxified at least partially byglutathione-S-transferase. Some studies have found genetic defects in the gene for this enzyme.[16]

Adrenochrome is also believed to havecardiotoxic properties.[17][18]

In popular culture

[edit]
Further information:QAnon § Child sex trafficking and satanic sacrifice
  • In his 1954 bookThe Doors of Perception,Aldous Huxley mentioned the discovery and the alleged effects of adrenochrome, which he likened to the symptoms ofmescaline intoxication, although he had never consumed it.[19]
  • Anthony Burgess mentions adrenochrome as "drencrom" at the beginning of his 1962 novelA 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 [...]"[19]
  • Hunter S. Thompson mentioned adrenochrome in his 1971 bookFear and Loathing in Las Vegas.[20] This is the likely origin of current myths surrounding this compound, because a character states that "There's only one source for this stuff ... 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'sfilm adaptation.[19] In the DVD commentary, directorTerry Gilliam admits that his and Thompson's portrayal is a fictional exaggeration. Gilliam insists that thedrug is entirely fictional and seems unaware of the existence of a substance with the same name. Hunter S. Thompson also mentions adrenochrome in his bookFear 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 fortycc's of adrenochrome."
  • Adrenochrome is the subject of severalconspiracy theories, includingQAnon andPizzagate,[21][22][23] in which the chemical plays a similar role toSatanic ritual abuse stories.[24] The theories commonly state that a cabal oftheistic Satanists rape and murder children, and harvest adrenochrome from their victims' blood as a recreational drug[25][26] or as anelixir of youth, similar tochildren's blood infusions.[27][28] In reality, adrenochrome has been produced byorganic synthesis since at least 1952,[7][29] is synthesized for research purposes bybiotechnology companies, who will then sell it to anyone; as it is not acontrolled substance, any medical or recreational use of the chemical is effortless to access.[30]

See also

[edit]

References

[edit]
  1. ^abHeacock RA, Nerenberg C, Payza AN (1 May 1958)."The Chemistry of the "Aminochromes": Part I. The Preparation and Paper Chromatography of Pure Adrenochrome".Canadian Journal of Chemistry.36 (5):853–857.Bibcode:1958CaJCh..36..853H.doi:10.1139/v58-124.
  2. ^Tamou Thahouly et al., Bovine Chromaffin Cells: Culture and Fluorescence Assay for Secretion, Methods Mol Biol 2021;2233:169-179. doi: 10.1007/978-1-0716-1044-2_11.
  3. ^"Adrenochrome Supplies for Sale."Aobious: a New Experience, Aibous. Aobious Products Catalog, aobious.com/aobious/products/13456-adrenochrome.html. Accessed 30 June 2025. Archived atInternet Archive.
  4. ^Veer WL (1942). "Melanin and its precursors II. On adrenochrome".Recueil des Travaux Chimiques des Pays-Bas.61 (9):638–646.doi:10.1002/recl.19420610904.
  5. ^Heacock RA (1 April 1959)."The Chemistry Of Adrenochrome And Related Compounds"(PDF).Chemical Reviews.59 (2):181–237.doi:10.1021/cr50026a001.
  6. ^abAbram Hoffer,Humphrey Osmond (1967).The Hallucinogens. Elsevier. pp. 272–273.doi:10.1016/c2013-0-12543-3.ISBN 978-1-4832-3296-6.LCCN 66030086.OCLC 332437.OL 35255701M.
  7. ^abSchayer, Richard W. (1952)."Synthesis of dl-Adrenalin-β-C14 and dl-Adrenochrome-β-C14".Journal of the American Chemical Society.74 (9).ACS Publications: 2441.Bibcode:1952JAChS..74.2441S.doi:10.1021/ja01129a531.Archived from the original on 25 October 2022. Retrieved25 October 2022.
  8. ^abSmythies J (January 2002). "The adrenochrome hypothesis of schizophrenia revisited".Neurotoxicity Research.4 (2):147–150.CiteSeerX 10.1.1.688.3796.doi:10.1080/10298420290015827.eISSN 1476-3524.ISSN 1029-8428.OCLC 50166444.PMID 12829415.S2CID 37594882.
  9. ^Hoffer A,Osmond H,Smythies J (January 1954). "Schizophrenia: A New Approach. II. Result of a Year's Research".The Journal of Mental Science.100 (418):29–45.doi:10.1192/bjp.100.418.29.eISSN 1472-1465.ISSN 0007-1250.LCCN 89649366.OCLC 1537306.PMID 13152519.S2CID 42531852.
  10. ^Hoffer A,Osmond H (First Quarter 1999)."The Adrenochrome Hypothesis and Psychiatry".The Journal of Orthomolecular Medicine.14 (1):49–62.ISSN 0834-4825.OCLC 15726974.S2CID 41468628.Archived from the original on 20 February 2024. Retrieved15 March 2024.
  11. ^Hoffer A (1994)."Schizophrenia: An Evolutionary Defense Against Severe Stress"(PDF).Journal of Orthomolecular Medicine.9 (4):205–2221.
  12. ^Lipton MA, Ban TA, Kane FJ, Levine J, Mosher LR, Wittenborn R (1973)."Task Force Report on Megavitamin and Orthomolecular Therapy in Psychiatry"(PDF). American Psychiatric Association. Archived fromthe original(PDF) on 23 February 2021. Retrieved7 September 2020.
  13. ^Wittenborn JR, Weber ES, Brown M (1973)."Niacin in the Long-Term Treatment of Schizophrenia".Archives of General Psychiatry.28 (3):308–315.doi:10.1001/archpsyc.1973.01750330010002.PMID 4569673.
  14. ^Ban TA, Lehmann HE (1970)."Nicotinic Acid in the Treatment of Schizophrenia: A Summary Report".Schizophrenia Bulletin.1 (3):5–7.doi:10.1093/schbul/1.3.5.
  15. ^Vaughan K, McConaghy N (1999). "Megavitamin and dietary treatment in schizophrenia: a randomised, controlled trial".Australian and New Zealand Journal of Psychiatry.33 (1):84–88.doi:10.1046/j.1440-1614.1999.00527.x.PMID 10197889.S2CID 38857700.
  16. ^Smythies J (2004). Smythies J (ed.).Disorders of Synaptic Plasticity and Schizophrenia (1st ed.). Elsevier Academic Press. pp. xv.ISBN 978-0-12-366860-8.
  17. ^Bindoli A, Rigobello MP, Galzigna L (July 1989). "Toxicity of aminochromes".Toxicology Letters.48 (1):3–20.doi:10.1016/0378-4274(89)90180-X.hdl:11577/2475305.PMID 2665188.
  18. ^Behonick GS, Novak MJ, Nealley EW, Baskin SI (December 2001). "Toxicology update: the cardiotoxicity of the oxidative stress metabolites of catecholamines (aminochromes)".Journal of Applied Toxicology.21 (S1):S15 –S22.doi:10.1002/jat.793.PMID 11920915.S2CID 27865845.
  19. ^abcAdams J (7 April 2020)."The truth about adrenochrome".The Spinoff. Retrieved28 June 2020.
  20. ^Friedberg B."The Dark Virality of a Hollywood Blood-Harvesting Conspiracy".Wired. Retrieved21 February 2021.
  21. ^"Fear and adrenochrome".Spectator USA. 4 May 2020. Archived fromthe original on 20 September 2020. Retrieved23 May 2020.
  22. ^"How Facebook connects 'pizzagate' conspiracy theorists".NBC News. February 2019. Retrieved23 May 2020.
  23. ^Dunning B (20 October 2020)."Skeptoid #750: How to Extract Adrenochrome from Children".Skeptoid. Retrieved20 October 2020.
  24. ^Kantrowitz L (29 September 2020)."QAnon, Blood Libel, and the Satanic Panic".The New Republic. Retrieved8 May 2021.
  25. ^Friedberg B (31 July 2020)."The Dark Virality of a Hollywood Blood-Harvesting Conspiracy".Wired. Retrieved16 February 2022.
  26. ^Hitt T (14 August 2020)."How QAnon Became Obsessed With 'Adrenochrome,' an Imaginary Drug Hollywood Is 'Harvesting' from Kids".The Daily Beast. Retrieved27 January 2021.
  27. ^Children's blood infusions
  28. ^"QAnon: A Glossary".Anti-Defamation League. 21 January 2021. Retrieved15 February 2022.
  29. ^"Method of synthesizing adrenochrome monoaminoguanidine".Google Patents. 1965.Archived from the original on 16 October 2021. Retrieved25 October 2022.
  30. ^Walker-Journey, Jennifer (14 April 2021)."Untangling the Medical Misinformation Around Adrenochrome".HowStuffWorks.Archived from the original on 14 April 2021. Retrieved25 October 2022.

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