MedKoo Cat#: 528403 | Name: SEP-174559

Description:

WARNING: This product is for research use only, not for human or veterinary use.

SEP-174559, also known as (S)-Desmethylzopiclone and (S)-DMZ, is a gamma-aminobutyric acid (GABA) receptor agonist potentially for the treatment of anxiety and muscle spasticity. Micromolar concentrations of SEP-174559 potentiated GABA(A) receptor currents evoked by subsaturating concentrations of GABA. The potentiation was related to a leftward shift in the GABA dose-response curves, suggesting the drug acts to increase GABA binding affinity. SEP-174559 and its parent compound, racemic zopiclone, were not selective between alpha1-, alpha2-, or alpha3-bearing GABA(A) receptors. SEP-174559 did not affect serotonin type-3 receptor function but was found to inhibit nicotinic acetylcholine (nACh) receptors. SEP-174559 inhibited N-methyl-D-aspartate (NMDA) receptor currents but did not affect non-NMDA receptors.

Chemical Structure

SEP-174559
SEP-174559
CAS#151776-26-0

Theoretical Analysis

MedKoo Cat#: 528403

Name: SEP-174559

CAS#: 151776-26-0

Chemical Formula: C16H15ClN6O3

Exact Mass: 374.0894

Molecular Weight: 374.79

Elemental Analysis: C, 51.28; H, 4.03; Cl, 9.46; N, 22.42; O, 12.81

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
SEP-174559; SEP 174559; SEP174559; (S)-DMZ; (S) DMZ; (S)DMZ; (S)-Desmethylzopiclone; (S) Desmethylzopiclone; (S)Desmethylzopiclone
IUPAC/Chemical Name
(S)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl piperazine-1-carboxylate
InChi Key
CGSFZSTXVVJLIX-HNNXBMFYSA-N
InChi Code
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/t15-/m0/s1
SMILES Code
O=C(N1CCNCC1)O[C@@H]2N(C3=NC=C(Cl)C=C3)C(C4=NC=CN=C42)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 374.79 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: de Albuquerque NC, de Gaitani CM, de Oliveira AR. A new and fast DLLME-CE method for the enantioselective analysis of zopiclone and its active metabolite after fungal biotransformation. J Pharm Biomed Anal. 2015 May 10;109:192-201. doi: 10.1016/j.jpba.2015.02.039. PubMed PMID: 25778930. 2: Gal J. New single-isomer compounds on the horizon. CNS Spectr. 2002 Apr;7(4 Suppl 1):45-54. PubMed PMID: 15131493. 3: Atack JR. Anxioselective compounds acting at the GABA(A) receptor benzodiazepine binding site. Curr Drug Targets CNS Neurol Disord. 2003 Aug;2(4):213-32. Review. PubMed PMID: 12871032. 4: McMahon LR, Jerussi TP, France CP. Stereoselective discriminative stimulus effects of zopiclone in rhesus monkeys. Psychopharmacology (Berl). 2003 Jan;165(3):222-8. PubMed PMID: 12434260. 5: Fleck MW. Molecular actions of (S)-desmethylzopiclone (SEP-174559), an anxiolytic metabolite of zopiclone. J Pharmacol Exp Ther. 2002 Aug;302(2):612-8. PubMed PMID: 12130723. 6: Carlson JN, Haskew R, Wacker J, Maisonneuve IM, Glick SD, Jerussi TP. Sedative and anxiolytic effects of zopiclone's enantiomers and metabolite. Eur J Pharmacol. 2001 Mar;415(2-3):181-9. PubMed PMID: 11274997. 7: Mannaert E, Tytgat J, Daenens P. Development of a stereospecific radioimmunoassay for the analysis of zopiclone and metabolites in urine. Clin Chim Acta. 1996 Sep 30;253(1-2):103-15. PubMed PMID: 8879842.