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), 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. 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. In what they called the "adrenochrome hypothesis", they speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome. There has been controversy about whether adrenochrome can be classified as a psychotropic drug. In Schizophrenic patients, adrenolutin and adrenochrome--breakdown products from the body's own epinephrine. Both are associated with biochemically based schizophrenia.Adrenochrome is a hallucinogen which also inhibits nerve cell transmission. If the body is making an excess of adrenochrome, from either stress or a poor biochemical ability to break it down into harmless by-products, we have the potential for brain dysfunction. A slowly emerging awareness from the scientific literature suggests there are a number of brain disturbances that are related to the accumulation of various neurotoxins in the brain. Adrenochrome has also been associated with treatment plans for patients with atrial fibrillation. High levels of stress release large amounts of adrenalin which in turn is oxidized to adrenochrome. Adrenochrome is known to cause fibrillation and other cardiac dysfunctions. Adrenochrome is a natural free radical and is primarily produced in the heart tissue, but circulates in the blood throughout the body. It can cross the blood-brain barrier and excessive amounts of it are believed to be a main cause of schizophrenia. Antioxidants protect against the formation of excessive amounts of adrenochrome and schizophrenics have been successfully treated with large amounts of niacin and ascorbic acid. Penicillamine has also been successfully used in the treatment of schizophrenia. Dr. Hoffer points out that adrenochrome is not all bad. He believes that the leucocytes use adrenochrome to destroy abnormal cells like cancer cells and that we therefore need a certain amount of adrenochrome in order to control cancer. The fact that schizophrenics rarely develop cancer supports this hypothesis. Dr. Hoffer concludes that we need a certain amount of stress in order to produce enough adrenochrome to enable our leucocytes to kill bacteria and tumor cells. However, we also need an adequate supply of natural antioxidants such as vitamins C and E and beta-carotene in order to neutralize an excess of adrenochrome after its work is done.

Mysticism

The question of religious chemistry has been underscored recently by the wide attention given to the theories, already mentioned, of Dr. Abram Hoffer and Humphry Osmond. Their adrenochrome-adrenolutin hypothesis suggests that schizophrenia may be caused at least in part by defective adrenal metabolism. Very briefly, the adrenal gland secretes the hormone adrenaline, which helps coordinate biological mechanisms in emergency situations--for example, a fist fight or a threatened traffic accident. Heart rate is increased, the blood is sugared up and pumped to the necessary muscles. Adrenaline also may affect the emotions, contributing to anxiety and depression. In the body it turns into a toxic hormone called adrenochrome, which in turn can be converted into either of two other compounds: dihydroxyindole or adrenolutin. It is possible that dihydroxyindole balances off adrenaline to reduce tension and irritability; in schizophrenics, however, adrenochrome is converted primarily into adrenolutin, which also is toxic, and the combination of adrenochrome-adrenolutin results in a poisonous disruption of the brain's chemical processes. The Hoffer-Osmond studies are far from conclusive, and similar theories have been advanced in the past. But the studies hold promise, and they are receiving serious consideration--due in part, no doubt, to the significance they have in other areas of current debate, including religion. The line dividing insanity and mysticism has never been too sharply drawn, and the biochemical theory of schizophrenia makes it all the more tenuous. Vitamin B-3 actually has cured cases of schizophrenia, according to Dr. Hoffer and Osmond. But Vitamin B-3 also has proved effective in terminating LSD experiences, and the implications of this must be obvious.

In popular culture

• Adrenochrome is mentioned in The Doors of Perception by Aldous Huxley as "a product of the decomposition of adrenaline" that can "produce many of the symptoms observed in mescaline intoxication."
• 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". 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.
• Adrenochrome Dreams is a song by the heavy metal band Otep, originally released as a hidden track on their 2007 album The Ascension.
• Appetite for Adrenochrome is the title of the debut album by Sacramento, California pop-punk band the Groovie Ghoulies.
• Adrenochrome is a song by the band Emeralds, released on their 2012 album, Just to Feel Anything.
• Adrenochrome or C9H9NO3 is a concept by Nikhil Carneiro, based on the fictitious drug from Fear and Loathing in Las Vegas The short film was executed by Carneiro and his college friends, and is now available on YouTube. It revolves around the drug, its procurement, and a teenager's addiction to it.
• Adrenochrome is mentioned in Terry Pratchett's Discworld Novel Sourcery. The book describes the wizard Rincewind loooking "like someone who had just eaten a handful of pineal glands and washed them down with a pint of adrenochrome" after he is overwhelmed by a magical field. Sourcery was first published in 1988.

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)