Adrenochrome - Wikipedia

Adrenochrome
Names
IUPAC name

3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione

Other names

Adraxone; Pink adrenaline

Identifiers
ChemSpider
ECHA InfoCard 100.000.176

  • InChI=1S/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3

      Y

    Key: RPHLQSHHTJORHI-UHFFFAOYSA-N

      Y

  • 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

  • O=C1\C=C2/C(=C\C1=O)N(CC2O)C

Properties
C 9H 9N O 3
Molar mass 179.175  g·mol−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  Y N  ?)
Infobox references

Adrenochrome is a chemical compound with the molecular formula C9H9NO3 produced by the oxidation of adrenaline (epinephrine). The derivative carbazochrome is a hemostatic medication. Despite a similarity in chemical names, it is unrelated to chrome or chromium.

Chemistry [ edit ]

In vivo, adrenochrome is synthesized by the oxidation of epinephrine. In vitro, silver oxide (Ag2O) is used as an oxidizing agent.[1] Its presence is detected in solution by a pink color. The color turns brown upon polymerization.

Effect on the brain [ edit ]

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, euphoria and derealization.[2] 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.[3] In what they called the "adrenochrome hypothesis",[4] they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.[5][6] 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.[7] Multiple additional studies in the United States,[8] Canada,[9] and Australia[10] 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 schizophrenics. In the early 2000s, interest was renewed by the discovery that adrenochrome may be produced normally as an intermediate in the formation of neuromelanin. 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.[11]

Legal status [ edit ]

Adrenochrome is unscheduled by the Controlled Substances Act in the United States. It is not an approved drug product by the Food and Drug Administration, and if produced as a dietary supplement it must comply with good manufacturing practice.[12]

In popular culture [ edit ]

References [ edit ]

  1. ^ MacCarthy, Chim, Ind. Paris 55,435(1946)
  2. ^ Smythies J (March 2002). "The adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research. 4 (2): 147–50. CiteSeerX 10.1.1.688.3796 . doi:10.1080/10298420290015827. PMID 12829415.
  3. ^ 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.
  4. ^ Hoffer A (1999). "The Adrenochrome Hypothesis and Psychiatry". The Journal of Orthomolecular Medicine. 14 (1): 49–62.
  5. ^ Hoffer A, Osmond H (1967). The Hallucinogens. Academic Press. ISBN 978-1-4832-6169-0.
  6. ^ Hoffer A (1994). "Schizophrenia: An Evolutionary Defense Against Severe Stress" (PDF) . Journal of Orthomolecular Medicine. 9 (4): 205–221.
  7. ^ Lipton M; et al. (1973). "Task Force Report on Megavitamin and Orthomolecular Therapy in Psychiatry". American Psychiatric Association.
  8. ^ Wittenborn JR, Weber ES, Brown M (1973). "Niacin in the Long-Term Treatment of Schizophrenia". Archives of General Psychiatry. 28 (3): 308–15. doi:10.1001/archpsyc.1973.01750330010002. PMID 4569673.
  9. ^ "Nicotinic Acid in the Treatment of Schizophrenia: A Summary Report". Schizophrenia Bulletin. 1 (3): 5–7. 1970. doi:10.1093/schbul/1.3.5 .
  10. ^ Vaughan K, McConaghy N (1999). "Megavitamin and dietary treatment in schizophrenia: a randomised, controlled trial". Australian and New Zealand Journal of Psychiatry. 33 (1): 84–8. doi:10.1046/j.1440-1614.1999.00527.x. PMID 10197889.
  11. ^ John Smythies (2004). Smythies, John (ed.). Disorders of Synaptic Plasticity and Schizophrenia (1st ed.). Elsevier Academic Press. pp. xv. ISBN 9780123668608.
  12. ^ "Compound summary for adrenochrome". National Center for Biotechnology Information, PubChem Database . Retrieved 2020-01-22 .
  13. ^ "Inspector Lewis Series Synopsis". Archived from the original on 2008-06-26.
  14. ^ Trevor Simms (August 14, 2016). "Adrenochrome movie trailer". Youtube. Retrieved 26 March 2020.
  15. ^ Alex Nichols (June 6, 2019). "Slender Man for Boomers". The Outline. Retrieved 16 March 2020.

External links [ edit ]

https://en.wikipedia.org/wiki/Adrenochrome