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Desmethylzopiclone

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Major metabolite of the hypnotic medication zopiclone
Desmethylzopiclone
Names
IUPAC name pyrazin-7-yl] piperazine-1-carboxylate
Other names SEP-174559
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
EC Number
  • 696-167-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C16H15ClN6O3/c17-10-1-2-11(21-9-10)23-14(24)12-13(20-4-3-19-12)15(23)26-16(25)22-7-5-18-6-8-22/h1-4,9,15,18H,5-8H2Key: CGSFZSTXVVJLIX-UHFFFAOYSA-N
SMILES
  • C1CN(CCN1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
Properties
Chemical formula C16H15ClN6O3
Molar mass 374.79 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Desmethylzopiclone, also known as SEP-174559, is an active metabolite of the sedative-hypnotic drug zopiclone.

Pharmacology

Unlike its parent compound, which is a largely non-selective benzodiazepine receptor agonist, desmethylzopiclone is a selective partial agonist at the benzodiazepine site of α3-containing GABA receptor subtypes. It is also an antagonist to nicotinic acetylcholine receptors and NMDA receptors.

Desmethylzopiclone has been described as a potential anxio-selective metabolite of zolpiclone owing to its selective affinity for the modulation of α3-containing GABA receptor subtypes. Modulation of these GABAA subtypes have been implicated as key mediators of the anxiolytic effects of benzodiazepines.

In forensic analysis

The quantification of desmethylzopiclone from urine has been demonstrated and may serve useful in forensic analysis of cases involving zolpiclone intoxication.

References

  1. ^ Fleck, Mark W. (2002-08-01). "Molecular Actions of (S)-Desmethylzopiclone (SEP-174559), an Anxiolytic Metabolite of Zopiclone". Journal of Pharmacology and Experimental Therapeutics. 302 (2): 612–618. doi:10.1124/jpet.102.033886. ISSN 0022-3565. PMID 12130723.
  2. Rowlett, James K.; Platt, Donna M.; Lelas, Snjezana; Atack, John R.; Dawson, Gerard R. (2005-01-18). "Different GABAA receptor subtypes mediate the anxiolytic, abuse-related, and motor effects of benzodiazepine-like drugs in primates". Proceedings of the National Academy of Sciences. 102 (3): 915–920. Bibcode:2005PNAS..102..915R. doi:10.1073/pnas.0405621102. ISSN 0027-8424. PMC 545524. PMID 15644443.
  3. Nilsson, Gunnel H.; Kugelberg, Fredrik C.; Ahlner, Johan; Kronstrand, Robert (2014). "Quantitative Analysis of Zopiclone, N-desmethylzopiclone, Zopiclone N-oxide and 2-Amino-5-chloropyridine in Urine Using LC–MS-MS". Journal of Analytical Toxicology. 38 (6): 327–334. doi:10.1093/jat/bku042. PMID 24790062.
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