Desmethylzopiclone

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Desmethylzopiclone
Desmethylzopiclone.svg
Names
IUPAC name
[6-(5-Chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] piperazine-1-carboxylate
Other names
SEP-174559
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 696-167-8
PubChem CID
UNII
  • 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,5-8H2
    Key: CGSFZSTXVVJLIX-UHFFFAOYSA-N
  • C1CN(CCN1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
Properties
C16H15ClN6O3
Molar mass 374.79 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

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. [1] It is also an antagonist to nicotinic acetylcholine receptors and NMDA receptors. [1]

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. [1] Modulation of these GABAA subtypes have been implicated as key mediators of the anxiolytic effects of benzodiazepines. [2]

In forensic analysis

A method for the quantification of desmethylzopiclone from urine has been developed and may serve useful in forensic analysis of cases involving zolpiclone intoxication. [3]

References

  1. 1 2 3 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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