adrenochrome

Adrenochrome
IUPAC name 3-hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione
Identifiers
CAS number	54-06-8 N
PubChem	5898
ChemSpider	5687 Y
Jmol-3D images	Image 1
SMILES O=C1\C=C2/C(=C\C1=O)N(CC2O)C
InChI 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
Properties
Molecular formula	C9H9NO3
Molar mass	179.17 g mol−1
Density	3.264 g/cm³
Boiling point	(decomposes, 115-120 °C)
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Chemistry

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.

Law

Adrenochrome is uncontrolled in the United States. Thus, it is generally 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 neurotoxic psychotomimetic substance and may be responsible for 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] There has been controversy about whether adrenochrome can be classified as a psychotropic drug.^[6]

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 extractor; 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".^[7] 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.

• In Anthony Burgess' A Clockwork Orange, Drencrom, a cocktail made with Adrenochrome is one of the drug-laced milk drinks available in the Korova Milk Bar.

• Adrenochrome is featured in Season 1, Episode 1, "Whom the Gods Would Destroy," of the British crime series Inspector Lewis.

• Adrenochrome is a song by British band The Sisters of Mercy, originally released on their 1982 single Body Electric, and subsequently on their compilation album Some Girls Wander by Mistake. The band You Shriek released a cover in April 2012.

References

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)