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Names | |
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IUPAC name 3-Hydroxy-1-methyl-2,3-dihydro-1H-indole-5,6-dione | |
Other names Adraxone; Pink adrenaline | |
Identifiers | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.000.176 |
EC Number |
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PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
Properties | |
C9H9NO3 | |
Molar mass | 179.175 g·mol−1 |
Appearance | deep-violet [1] |
Density | 3.785 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). |
Adrenochrome is a chemical compound produced by the oxidation of adrenaline (epinephrine). It was the subject of limited research from the 1950s through to the 1970s as a potential cause of schizophrenia. While it has no current medical application, the semicarbazide derivative, carbazochrome, is a hemostatic medication.
Despite this compound's name, it is unrelated to the element chromium; instead, the ‑chrome suffix indicates a relationship to color, as pure adrenochrome has a deep violet color. [1]
The oxidation reaction that converts adrenaline into adrenochrome occurs both in vivo and in vitro . Silver oxide (Ag2O) was among the first reagents employed for this, [2] but a variety of other oxidizing agents have been used successfully. [3] In solution, adrenochrome is pink and further oxidation of the compound causes it to polymerize into brown or black melanin compounds. [4]
Adrenochrome is readily synthesized from commercially available reagents: chloroacetic acid and catechol react in the presence of phosphoryl chloride to yield chloroacetylcatechol. After purification, chloroacetylcatechol is reacted with aqueous methylamine and treated with hydrochloric acid, yielding adrenalone hydrochloride. This is then hydrogenated to racemic adrenaline. Finally, adrenaline is oxidized to adrenochrome by an appropriate oxidizing agent such as silver oxide. [5]
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 and derealization. [6]
In 1954, 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. [7] . In what Hoffer called the "adrenochrome hypothesis", [8] he and Osmond in 1967 speculated that megadoses of vitamin C and niacin could cure schizophrenia by reducing brain adrenochrome. [9] [10]
The treatment of schizophrenia with such potent anti-oxidants is controversial. 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. [11] Multiple additional studies in the United States, [12] Canada, [13] and Australia [14] 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 people with schizophrenia.[ citation needed ]
In the early 2000s, interest was renewed by the discovery that adrenochrome may be produced normally as an intermediate in the formation of neuromelanin. [6] 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. [15]
Adrenochrome is also believed to have cardiotoxic properties. [16] [17]