N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

• ChemBase ID: 104021
• Molecular Formular: C13H16N2O3
• Molecular Mass: 248.27774
• Monoisotopic Mass: 248.11609238
• SMILES: COc1cc2c([nH]cc2CCNC(=O)C)cc1O
• Canonical SMILES: COc1cc2c(CCNC(=O)C)c[nH]c2cc1O
• InChI: InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)
• InChIKey: OMYMRCXOJJZYKE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• IUPAC Traditional name: N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide
• Synonyms: 6-Hydroxymelatonin; N-[2-(6-Hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide; 6-Hydroxy-N-acetyl-5-methoxytryptamine; 6-Hydroxy Melatonin; 3-(N-Acetylaminoethyl)-6-hydroxy-5-methoxyindole; 6-HYDROXYMELATONIN

Database IDs

• CAS Number: 2208-41-5
• MDL Number: MFCD00037971
• PubChem SID: 162090920; 24278458
• PubChem CID: 1864

CALCULATED PROPERTIES

• Acid pKa: 9.2939
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 0.843978
• LogD (pH = 7.4): 0.8385781
• Log P: 0.8440475
• Molar Refractivity: 68.2608 cm^3
• Polarizability: 27.220165 Å^3
• Polar Surface Area: 74.35 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble; Chloroform; Methanol
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 172-175°C

Safety Information

• Storage Condition: 2-8°C, Store Under Nitrogen; Refrigerator
• RTECS: AC3607000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-40
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

Pharmacology Properties

• Gene Information: human ... MTNR1A(4543), MTNR1B(4544)

DETAILS

MP Biomedicals - 02154151

Crystalline Metabolite of melatonin.

Sigma Aldrich - H0627

Biochem/physiol Actions
Melatonin metabolite with agonist activity.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H0627.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H944625

A metabolite of Melatonin (M215000).

REFERENCES

• Huether, G., et al.: Life Sci., 51, 945 (1992)
• Holmes, M., et al.: J. Clin. Oncol., 18, 3668 (1992)
• Roth, G., et al.: J. Clin. Endocrinol. Metab., 86, 3292 (1992)