Adrenochrome

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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
Identifiers
54-06-8 N
ChemSpider 5687 YesY
Jmol-3D images Image
PubChem 5898
Properties
C9H9NO3
Molar mass 179.17 g·mol−1
Density 3.264 g/cm³
Boiling point (decomposes, 115-120 °C)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Adrenochrome (catecholamine o-quinone),[1] chemical formula C9H9NO3, is a compound produced by the oxidation of adrenaline (epinephrine). The derivative carbazochrome is a hemostatic medication. It is unrelated to chrome (chromium).

Chemistry[edit]

In vivo, adrenochrome is synthesized by the oxidation of epinephrine. In vitro, silver oxide (Ag2O) is used as an oxidizing agent.[2] 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) were done in the 50s and 60s, reporting that adrenochrome triggered psychotic reactions like thought disorder, derealization, and euphoria.[3] It has never been scientifically accepted, however, that adrenochrome has psychedelic properties.[4] 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.[5] In what they called the "adrenochrome hypothesis",[6] they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.[7][8]

Law[edit]

Adrenochrome is unscheduled by the Controlled Substances Act in the United States, but if sold as a supplement, sales must conform to U.S. supplement laws. If sold for consumption as a food or drug, sales are regulated by the FDA.[9][unreliable source?]

In popular culture[edit]

References[edit]

  1. ^ COMMENTARY, John Smythies; Neurochemistry Section, Brain and Perception Laboratory, Center for Human Information Processing, UCSD Association for the Scientific Study of Consciousness, Electronic Seminars, 1999
  2. ^ MacCarthy, Chim, Ind. Paris 55,435(1946)
  3. ^ John Smythies (2002). "The adrenochrome hypothesis of schizophrenia revisited". Neurotoxicity Research 4 (2): 147–150. doi:10.1080/10298420290015827. 
  4. ^ "The controversy that these reports created just sort of died away, and the adrenochrome family has never been accepted as being psychedelic. No one in the scientific community today is looking in and about the area, and at present this is considered as an interesting historical footnote." As seen at: Alexander Shulgin and Ann Shulgin (1991). "#157 (TMA)". PiHKAL - A Chemical Love Story. Transform Press. 
  5. ^ Hoffer, A. Osmond, H., Smithies, J.; Schizophrenia: a new approach. Journal of Mental Science #100 (January, 1954)
  6. ^ Hoffer, A (Q1 1990). "The Adrenochrome Hypothesis and Psychiatry". Retrieved 2011-07-25.  Check date values in: |date= (help)
  7. ^ Hoffer, A. and Osmond, H. The Hallucinogens (Academic Press, 1967).
  8. ^ Hoffer, A., Osmond, H., & Smythies, J. (1994). An Evolutionary Defense Against Severe Stress. Schizophrenia: A New Approach (pp. 205–221). Victoria, Canada: Journal of Orthomolecular Medicine
  9. ^ Erowid. "Adrenochrome Law". Retrieved 2013-01-14. 
  10. ^ http://www.pbs.org/wgbh/masterpiece/lewis/destroy_synopsis.html

External links[edit]