(5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl(2H8)piperazine-1-carboxylate

• ChemBase ID: 168279
• Molecular Formular: C17H17ClN6O3
• Molecular Mass: 388.80828
• Monoisotopic Mass: 388.10506611
• SMILES: c1cnc2c(n1)C(=O)N([C@H]2OC(=O)N1CCN(CC1)C)c1ncc(cc1)Cl
• Canonical SMILES: CN1CCN(CC1)C(=O)O[C@H]1c2nccnc2C(=O)N1c1ccc(cn1)Cl
• InChI: InChI=1S/C17H17ClN6O3/c1-22-6-8-23(9-7-22)17(26)27-16-14-13(19-4-5-20-14)15(25)24(16)12-3-2-11(18)10-21-12/h2-5,10,16H,6-9H2,1H3/t16-/m0/s1
• InChIKey: GBBSUAFBMRNDJC-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H,6H,7H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl(^2H₈)piperazine-1-carboxylate
• IUPAC Traditional name: (5S)-6-(5-chloropyridin-2-yl)-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl(^2H₈)piperazine-1-carboxylate
• Synonyms: [(9S)-8-(5-Chloropyridin-2-yl)-7-oxo-2,5,8-triazabicyclo[4.3.0]nona-1,3,5-trien-9-yl]4-methylpiperazine-d8-1-carboxylate; Lunesta-d8; (S)-zopiclone-d8; Eszopiclone-d8

Database IDs

• PubChem SID: 162262411
• PubChem CID: 45039158

CALCULATED PROPERTIES

• Acid pKa: 13.038308
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.59504867
• LogD (pH = 7.4): 0.6902288
• Log P: 0.80654305
• Molar Refractivity: 95.8855 cm^3
• Polarizability: 37.123627 Å^3
• Polar Surface Area: 91.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 197-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E889152

Eszopiclone is the active stereoizomer of Zopiclone and belongs to the class of drug known as cyclopyrrones. It is a nonbenzodiazepine hypnotic agent used as a treatment for insomnia.This is a controlled substance (depressant) in the US but not in Canada.

REFERENCES

• Gottesmann, C., et al.: Eur. J. Neurosci., 10, 409 (1998)
• Yoshimoto, M., et al.: Eur. Neuropsychopharmacol., 9, 29 (1998)