(4S)-4-[(3-{2-[bis(2H3)methylamino]ethyl}-1H-indol-5-yl)methyl]-1,3-oxazolidin-2-one

• ChemBase ID: 179657
• Molecular Formular: C16H21N3O2
• Molecular Mass: 287.35684
• Monoisotopic Mass: 287.16337693
• SMILES: c1cc(cc2c1[nH]cc2CCN(C)C)C[C@@H]1NC(=O)OC1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(C[C@H]1COC(=O)N1)cc2)C
• InChI: InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
• InChIKey: ULSDMUVEXKOYBU-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(3-{2-[bis(^2H₃)methylamino]ethyl}-1H-indol-5-yl)methyl]-1,3-oxazolidin-2-one
• IUPAC Traditional name: (4S)-4-[(3-{2-[bis(^2H₃)methylamino]ethyl}-1H-indol-5-yl)methyl]-1,3-oxazolidin-2-one
• Synonyms: (4S)-4-[[3-[2-(Dimethyl-d6-amino)ethyl]-1H-indol-5-yl]methyl-2-oxazolidinone; BW-311C90-d6; Zomig-d6; Zolmitriptan-D6 (Major)

Database IDs

• PubChem SID: 164235567
• PubChem CID: 46783278

CALCULATED PROPERTIES

• Acid pKa: 13.002183
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3495891
• LogD (pH = 7.4): -0.08771248
• Log P: 2.0428753
• Molar Refractivity: 82.4392 cm^3
• Polarizability: 32.885006 Å^3
• Polar Surface Area: 57.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Isopropanol
• Apperance: White Crystalline Powder
• Melting Point: 58-60°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - Z639002

A Serotonin 5HTID-receptor agonist.

REFERENCES

• Glen, R.C., et al.: J. Med. Chem., 38, 3566 (1995)
• Seaber, E., et al.: Brit. J. Clin. Pharmacol., 41, 141 (1995)
• Tepper, S.J., et al.: Curr. Med. Res. Opin., 15, 254 (1999)