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Adrenochrome information


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
Other names
Adraxone; Pink adrenaline
Identifiers
CAS Number
  • (racemic): 54-06-8 checkY
  • (R)-Enantiomer: 7506-92-5
  • (S)-Enantiomer: 5181-82-8
3D model (JSmol)
  • (racemic): Interactive image
ChEBI
  • (racemic): CHEBI:166544
ChEMBL
  • (racemic): ChEMBL1314174
ChemSpider
  • (racemic): 5687 checkY
ECHA InfoCard 100.000.176 Edit this at Wikidata
EC Number
  • (racemic): 200-192-8
PubChem CID
  • (racemic): 5898
UNII
  • (racemic): 70G54NQL71 checkY
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 checkY
    Key: RPHLQSHHTJORHI-UHFFFAOYSA-N checkY
  • (racemic): 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
SMILES
  • (racemic): O=C1\C=C2/C(=C\C1=O)N(CC2O)C
Properties
Chemical formula
C9H9NO3
Molar mass 179.175 g·mol−1
Appearance deep-violet[1]
Density 3.264 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).
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Infobox references

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 coloration.[1]

  1. ^ a b Heacock RA, Nerenberg C, Payza AN (1 May 1958). "The Chemistry of the "Aminochromes": Part I. The Preparation and Paper Chromatography of Pure Adrenochrome". Canadian Journal of Chemistry. 36 (5): 853–857. doi:10.1139/v58-124.

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