N-[2-(1H-indol-3-yl)ethyl]acetamide

• ChemBase ID: 105297
• Molecular Formular: C12H14N2O
• Molecular Mass: 202.25236
• Monoisotopic Mass: 202.11061308
• SMILES: CC(=O)NCCc1c[nH]c2c1cccc2
• Canonical SMILES: CC(=O)NCCc1c[nH]c2c1cccc2
• InChI: InChI=1S/C12H14N2O/c1-9(15)13-7-6-10-8-14-12-5-3-2-4-11(10)12/h2-5,8,14H,6-7H2,1H3,(H,13,15)
• InChIKey: NVUGEQAEQJTCIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[2-(1H-indol-3-yl)ethyl]acetamide
• IUPAC Traditional name: N-[2-(1H-indol-3-yl)ethyl]acetamide; N-acetyltryptamine
• Synonyms: 3-(2-N-Acetylaminoethyl)indole; N-Acetyltryptamine; N-ACETYLTRYPTAMINE

Database IDs

• CAS Number: 1016-47-3
• MDL Number: MFCD00209910
• PubChem SID: 162093335; 24278235
• PubChem CID: 70547

CALCULATED PROPERTIES

• Acid pKa: 15.897049
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): 1.3052839
• LogD (pH = 7.4): 1.305284
• Log P: 1.305284
• Molar Refractivity: 59.8167 cm^3
• Polarizability: 24.133804 Å^3
• Polar Surface Area: 44.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: alcohol: soluble
• Apperance: powder

Safety Information

• Storage Condition: 2-8°C, Desiccate
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... MTNR1A(4543), MTNR1B(4544)
• Mechanism of Action: Antioxidant; Melatonin partial agonist (MT1/MT2); MT3 antagonist

Product Information

• Biological Source: Alkaloid from leaves of Prosopis nigra (Leguminosae)
• Application(s): Antioxidant; Regulator of triptamine-serotonine dependent disorders

DETAILS

MP Biomedicals - 02159685

Useful in determination of serotonin N-acetyl transferase

Sigma Aldrich - A7342

Biochem/physiol Actions
Mixed agonist-antagonist at melatonin receptors; antioxidant.

REFERENCES

• Dubocovich (1985) Characterization of a retinal melatonin receptor. J.Pharmacol.Exp.Ther. 234 395. Dubocovich (1988) Luzindole (NO 774):
• a novel melatonin receptor antagonist. J.Pharmacol.Exp.Ther. 246 902.