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 InfoCard 100.000.176 Edit 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 mass 179.175 g·mol−1
Appearance deep-violet[1]
Density 3.264 g/cm3
Boiling point 115–120 °C (239–248 °F; 388–393 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Adrenochrome is a chemical compound produced by the 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, carbazochrome, is a hemostatic medication.

Despite this compound's name, it is unrelated to the element chromium; instead, the ‑chrome suffix indicates a relationship to color, as pure adrenochrome is deep violet.[1]

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,[2] but a variety of other oxidising agents have been used successfully.[3] In solution, adrenochrome is pink and further oxidation of the compound causes it to polymerize into brown or black melanin compounds.[4]

History

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.[5]

In 1954, researchers Abram Hoffer and Humphry Osmond claimed that adrenochrome is a neurotoxic, psychotomimetic substance and may play a role in schizophrenia and other mental illnesses.[6]

In what Hoffer called the "adrenochrome hypothesis",[7] he and Osmond in 1967 speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.[8][9]

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.[10] Multiple additional studies in the United States,[11] Canada,[12] and Australia[13] similarly failed to find benefits of megavitamin therapy to treat 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]

In the early 2000s, interest was renewed by the discovery that adrenochrome may be produced normally as an intermediate in the formation of neuromelanin.[5] 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.[14]

Adrenochrome is also believed to have cardiotoxic properties.[15][16]

In popular culture

References

  1. ^ a b Heacock 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. doi:10.1139/v58-124.
  2. ^ 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.
  3. ^ Heacock RA (1 April 1959). "The Chemistry Of Adrenochrome And Related Compounds" (PDF). Chemical Reviews. 59 (2): 181–237. doi:10.1021/cr50026a001.
  4. ^ A. Hoffer, H. Osmond (22 October 2013). The Hallucinogens. Elsevier. pp. 272–273. ISBN 978-1-4832-6169-0.
  5. ^ a b Smythies J (March 2002). "The adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research. 4 (2): 147–150. CiteSeerX 10.1.1.688.3796. doi:10.1080/10298420290015827. PMID 12829415. S2CID 37594882.
  6. ^ Hoffer A, Osmond H, Smithies 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. PMID 13152519.
  7. ^ Hoffer A (1999). "The Adrenochrome Hypothesis and Psychiatry". The Journal of Orthomolecular Medicine. 14 (1): 49–62.
  8. ^ Hoffer A, Osmond H (1967). The Hallucinogens. Academic Press. ISBN 978-1-4832-6169-0.
  9. ^ Hoffer A (1994). "Schizophrenia: An Evolutionary Defense Against Severe Stress" (PDF). Journal of Orthomolecular Medicine. 9 (4): 205–2221.
  10. ^ 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 from the original (PDF) on 23 February 2021. Retrieved 7 September 2020.
  11. ^ 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.
  12. ^ 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.
  13. ^ 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.
  14. ^ 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.
  15. ^ 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. PMID 2665188.
  16. ^ 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.
  17. ^ a b c Adams J (7 April 2020). "The truth about adrenochrome". The Spinoff. Retrieved 28 June 2020.
  18. ^ Friedberg B. "The Dark Virality of a Hollywood Blood-Harvesting Conspiracy". Wired. Retrieved 21 February 2021.
  19. ^ "Fear and adrenochrome". Spectator USA. 4 May 2020. Archived from the original on 20 September 2020. Retrieved 23 May 2020.
  20. ^ "How Facebook connects 'pizzagate' conspiracy theorists". NBC News. February 2019. Retrieved 23 May 2020.
  21. ^ Dunning B (20 October 2020). "Skeptoid #750: How to Extract Adrenochrome from Children". Skeptoid. Retrieved 20 October 2020.
  22. ^ Kantrowitz L (29 September 2020). "QAnon, Blood Libel, and the Satanic Panic". The New Republic. Retrieved 8 May 2021.
  23. ^ Friedberg B (31 July 2020). "The Dark Virality of a Hollywood Blood-Harvesting Conspiracy". Wired. Retrieved 16 February 2022.
  24. ^ Hitt T (14 August 2020). "How QAnon Became Obsessed With 'Adrenochrome,' an Imaginary Drug Hollywood Is 'Harvesting' from Kids". The Daily Beast. Retrieved 27 January 2021.
  25. ^ "QAnon: A Glossary". Anti-Defamation League. 21 January 2021. Retrieved 15 February 2022.
  26. ^ Walker-Journey, Jennifer (14 April 2021). "Untangling the Medical Misinformation Around Adrenochrome". HowStuffWorks. Archived from the original on 14 April 2021. Retrieved 25 October 2022.
  27. ^ Schayer, Richard W. (1952). "Synthesis of dl-Adrenalin-β-C14 and dl-Adrenochrome-β-C14". Journal of the American Chemical Society. ACS Publications. 74 (9): 2441. doi:10.1021/ja01129a531. Archived from the original on 25 October 2022. Retrieved 25 October 2022.
  28. ^ "Method of synthesizing adrenochrome monoaminoguanidine". Google Patents. 1965. Archived from the original on 16 October 2021. Retrieved 25 October 2022.