Structural Formula Vector Image
Title: Adrenochrome
CAS Registry Number: 54-06-8
CAS Name: 2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dione
Additional Names: 3-hydroxy-1-methyl-5,6-indolinedione
Molecular Formula: C9H9NO3
Molecular Weight: 179.17
Percent Composition: C 60.33%, H 5.06%, N 7.82%, O 26.79%
Literature References: Pigment obtained by the oxidation of epinephrine. Prepn using Ag2O as oxidizing agent: MacCarthy, Chim. Ind. (Paris) 55, 435 (1946). Structure: D. E. Green, D. Richter, Biochem. J. 31, 596 (1937); J. Harley-Mason, Experientia 4, 307 (1948). Probably has the zwitterionic quinonimine structure shown here. Spectral data: A. Lund, Acta Pharmacol. Toxicol. 5, 1218 (1949). Review: R. A. Heacock, Chem. Rev. 59, 181-237 (1959). Review, as a psychotomimetic agent: R. A. Heacock, Chim. Ther. 6, 300 (1971).
Properties: Brilliant red crystals may exist as hemihydrate from methanol-formic acid, dec 115-120°. Absorption max (1 mg % aq sol): 220, 300, 485 nm (log e 4.33, 4.01, 3.64). Well-formed and well-dried crystals can be kept in a vacuum desiccator for several weeks. Easily oxidized to melanin. Freely sol in water; fairly sol in alcohol. Almost insol in benzene and ether. Solns are unstable. Optimum pH of water soln 4.0.
Absorption maximum: Absorption max (1 mg % aq sol): 220, 300, 485 nm (log e 4.33, 4.01, 3.64)
Derivative Type: Oxime sesquihydrate
CAS Registry Number: 6055-73-8
Molecular Formula: C9H10N2O3.1½H2O
Molecular Weight: 203.19
Percent Composition: C 53.20%, H 5.46%, N 13.79%, O 27.56%
Properties: Orange needles from water, mp 278°. Much more stable than adrenochrome.
Melting point: mp 278°
Derivative Type: Monosemicarbazone
CAS Registry Number: 69-81-8
Additional Names: Carbazochrome
Trademarks: Adrenoxyl (Sanofi Winthrop); Cromosil (Zambeletti)
Molecular Formula: C10H12N4O3
Molecular Weight: 236.23
Percent Composition: C 50.84%, H 5.12%, N 23.72%, O 20.32%
Literature References: Prepn: Dechamps et al., US 2506294 (1950 to Société Belge de l'Azote).
Properties: Orange-red crystals from dil alcohol, mp 203° (dec). See also Carbazochrome Salicylate.
Melting point: mp 203° (dec)
Derivative Type: Thiosemicarbazone
CAS Registry Number: 113185-69-6
Molecular Formula: C10H12N4O2S
Molecular Weight: 252.29
Percent Composition: C 47.61%, H 4.79%, N 22.21%, O 12.68%, S 12.71%
Literature References: Description: Fleischhacker, Barsel, US 2712024 (1955 to International Hormones).
Properties: mp 215-220°.
Melting point: mp 215-220°
Therap-Cat: Monosemicarbazone as hemostatic.
Keywords: Hemostatic.

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