3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione

• ChemBase ID: 108184
• Molecular Formular: C9H9NO3
• Molecular Mass: 179.17266
• Monoisotopic Mass: 179.05824315
• SMILES: CN1CC(O)C2=CC(=O)C(=O)C=C12
• Canonical SMILES: OC1CN(C2=CC(=O)C(=O)C=C12)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
• InChIKey: RPHLQSHHTJORHI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-hydroxy-1-methyl-2,3,5,6-tetrahydro-1H-indole-5,6-dione
• IUPAC Traditional name: adrenochrome
• Synonyms: Adrenochrome; 3-Hydroxy-1-methyl-5,6-indolinedione,2,3-Dihydro-3-hydroxy-1-methyl-1H-indole-5,6-dione; D,L-Adrenochrome; L-ADRENOCHROME, FREE BASE; 3-Hydroxy-1-methyl-5,6-indolinedione; Adrenochrome

Database IDs

• CAS Number: 54-06-8
• EC Number: 200-192-8
• MDL Number: MFCD00069732
• PubChem SID: 162094056; 24891016
• PubChem CID: 5898
• Chemspider ID: 5687
• Wikipedia Title: Adrenochrome

CALCULATED PROPERTIES

• Acid pKa: 14.092155
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.3232714
• LogD (pH = 7.4): -0.31320494
• Log P: -0.31307498
• Molar Refractivity: 48.556 cm^3
• Polarizability: 17.325603 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 50 mg in 1 mL 1M Sodium Hydroxide Gives a Dark Brown Solution
• Apperance: Red Solid
• Melting Point: >110°C (dec.)
• Boiling Point: (decomposes, 115-120 °C)
• Density: 3.264 g/cm3

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• RTECS: NM1925000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

MP Biomedicals - 05206373

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A5752

Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A5752.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A305250

The substance mainly responsible for the red colours produced during the mild oxidation of adrenaline

REFERENCES

• Costa, V., et al.: Chem. Res. Toxicol., 20, 1183 (2007)
• Sotomayor-Zarate, R., et al.: Biol Reproduc., 78, 673 (2007)