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Zopiclon
imovane · Zopiclone R-IsoMer CIV · 6-(5-Chloro-2-pyridinyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-yl 4-methyl-1-piperazinecarboxylate · Amoban · Imobam · Limovan · Amovane · Sopivan
Identifikatoren & physikalische Daten
| CAS No. | 43200-80-2 |
|---|---|
| Summenformel | C17H17ClN6O3 |
| Durchschnittliche Molmasse | 388,8 g/mol |
| Monoisotopische Masse | 388,10506608 g/mol |
| SMILES | CN1CCN(C(=O)OC2c3nccnc3C(=O)N2c2ccc(Cl)cn2)CC1 |
| InChIKey | GBBSUAFBMRNDJC-UHFFFAOYSA-N |
| PubChem CID | 5735 |
| ChEMBL | CHEMBL135400 |
| ChEBI | CHEBI:32315 |
| EC No. | 256-138-9 |
| DTXSID | DTXSID4041155 |
| Lokaler Name | Zopiclon |
Chemische & physikalische Eigenschaften
| XLogP | 0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 91,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 7 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 27 |
| Formalladung | 0 |
| Komplexität | 573 |
| Arzneimittel | DEA NFLIS-Drug Category -> Depressants and TranquilizersDEA Schedule IV Controlled Substance -> DepressantsPharmaceuticals -> HypnoticPharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| LogP (Verteilungskoeffizient) | 0.81.1 |
| Löslichkeit | 8.85e-01 g/L>58.3 [ug/mL] (The mean of the results at pH 7.4)DMSO: 2 mg/mL |
| Human Drugs | Pharmaceuticals |
| Schmelzpunkt | 178 °C1780C |
| Physical Description | Solid |
| Collision Cross Section | 188.5 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]186.5 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]176.57 Ų [M+H-H2O]+ [CCS Type: TW |
| Siedepunkt | 580.7±50.0 °C(Predicted) |
| Dichte | 1.1105 (estimate) |
| Flammpunkt | 2℃ |
| Lagerbedingungen | Store at RT |
| pKa (Säurekonstante) | pKa ﹣1.5±0.1(10% ACN in aq. H2SO4 t = 25.0) (Uncertain) |
| Aggregatzustand | Solid |
| Farbe | White to Off-White |
| Stabilität | Hygroscopic |
| Hauptanwendungen | clinical testing |
| 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/p+1 |
| InChIKey | GBBSUAFBMRNDJC-UHFFFAOYSA-N |
| SMILES | C[NH+]1CCN(CC1)C(=O)OC2N(C(=O)c3nccnc23)c4ccc(Cl)cn4 |
| CAS Datenbank | 43200-80-2(CAS DataBase Reference) |
| NIST chemische Informationen | Zopiclone(43200-80-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302+H312+H332 (20.1%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 139 reports by companies from 19 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | DEA schedule IV controlled substanceZopiclone: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Gesundheitliche Auswirkungen | They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. |
| Expositionspfade | Rapidly absorbed following oral administration. |
| Toxizitätsübersicht | Zopiclone exerts its action by binding on the benzodiazepine receptor complex and modulation of the GABA<sub>B</sub>Z receptor chloride channel macromolecular complex. Both zopiclone and benzodiazepines act indiscriminately at the benzodiazepine binding site on alpha1, alpha2, alpha3 and alpha5 GABAA containing receptors as full agonists causing an enhancement of the inhibitory actions of GABA to produce the therapeutic (hypnotic and anxiolytic) and adverse effects of zopiclone. |
| Signs and Symptoms | Rare individual instances of fatal outcomes following overdose with racemic zopiclone have been reported in European postmarketing reports, most often associated with overdose with other CNS-depressant agent. Signs and symptoms of overdose effects of CNS depressants can be expected to present as exaggerations of the pharmacological effects noted in preclinical testing. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)ZopicloneDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 1648 3 / PGII |
| Zollcode | 29339900 |
| RTECS-Nr. | TL1425000 |
| R-Sätze (R) | 20/21/22-36/37/38-62-36-11 |
| Toxizität | mouse,LD50,intramuscular,541mg/kg (541mg/kg),LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSIONBEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY),Oyo Yakuri. Pharmacometrics. Vol. 26, Pg. 935, 1983. |
| Gefahrensymbole | Xn,Xi,F |
| Sicherheitshinweise (S) | 26-36-36/37-16 |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrenklasse | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Flam. Liq. 2 |
Anwendungen & Verwendung
Beschreibung
Zopiclone is an effective hypnotic agent with a short duration of action. Although it interacts with the benzodiazepine receptor complex, it is reported to have minimal effects on memory, little synergy with alcohol, and low abuse potential.
Verwenden
Cyclopyrrolone member of a family of non-benzodiazepine GABAA receptor agonists. This is a controlled substance (depressant) in the US but not in Canada. Sedative, hypnotic