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Adrenochrome
IUPAC name	2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dione
Identifiers
CAS number	54-06-8
PubChem	5898
SMILES	O=C1\C=C2/C(=C\C1=O)N(CC2O)C
InChI	1/C9H9NO3/c1-10-4-9(13)5-2-7(11)8(12)3-6(5)10/h2-3,9,13H,4H2,1H3
InChI key	RPHLQSHHTJORHI-UHFFFAOYAD
ChemSpider ID	5687
Properties
Molecular formula	C9H9NO3
Molar mass	179.17 g mol−1
Density	3.264 g/cm³
Boiling point	(decomposes, 115-120 °C)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Adrenochrome, chemical formula C₉H₉NO₃, is a pigment obtained by the oxidation of adrenaline (epinephrine). Adrenochrome monosemicarbazone, also known as carbazochrome, is a hemostatic, meaning it reduces capillary bleeding.

Chemistry

Adrenochrome is synthesized in vivo 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, and turns brown upon polymerization.

Law

Adrenochrome is uncontrolled in the United States. This means it is generally considered legal to buy, possess, and distribute (sell, trade or give). 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.

Psychoactivity

Megavitamin therapy advocates Abram Hoffer and Humphry Osmond claimed that adrenochrome is a hallucinogenic substance and may be responsible for schizophrenia and other mental illnesses. In what they called the "adrenochrome hypothesis", they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome.^[2] There has been controversy about whether adrenochrome can be classified as a psychotropic drug.^[3]

In popular culture

Author Hunter S. Thompson mentions adrenochrome in his book Fear and Loathing in Las Vegas. In the book it is derived from a living donor's adrenal gland (removing the gland kills the donor; it cannot be taken from a corpse). As such, it is purported to be very exotic, and very intense: "the first wave felt like a combination of mescaline and methedrine". Thompson reported a significant perceived rise in body temperature that led to paralysis. The adrenochrome scene also appears in the novel's film adaptation. In the DVD commentary, director Terry Gilliam admits that his and Thompson's portrayal is a fictional exaggeration. In fact, Gilliam insists that the drug is entirely fictional and seems unaware of the existence of a substance with even a similar name. Thompson also mentions the substance in his book Fear and Loathing on the Campaign Trail '72.

References

1. ^ MacCarthy, Chim, Ind. Paris 55,435(1946)
2. ^ Hoffer, A. and Osmond, H. The Hallucinogens (Academic Press, 1967).
3. ^ Erowid Adrenochrome Vault

External links

• Adrenochrome Commentary at erowid.org
• Adrenochrome deposits resulting from the use of epinephrine-containing eye drops used to treat glaucoma from the Iowa Eye Atlas (searched for diagnosis = adrenochrome)