Grundinformationen
- Standard-SMILES
CCC1(CC)C(=O)NC(=O)NC1=O- InChIKey
FTOAOBMCPZCFFF-UHFFFAOYSA-N- Summenformel
- C8H12N2O3
- Durchschnittliche Molmasse
- 184,19 g/mol
- Monoisotopische Masse
- 184,08479224
Überblick
5,5-diethylbarbituric acid is a member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid). It has a role as a drug allergen.
Namen und Bezeichner
- Bevorzugter Name
- Barbital
- IUPAC
- 5,5-diethyl-1,3-diazinane-2,4,6-trione
- Lokaler Name
- Barbital
- Englischer Name
- BARBITAL
- Summenformel
- C8H12N2O3
- Molmasse
- 184.19
Namen und Synonyme
barbitalBarbitone5,5-Diethylbarbituric acid57-44-3DiethylmalonylureaEthylbarbitalDiemalDEBADTXSID50226435,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione5WZ53ENE2PNSC-31352
Weitere Namen anzeigen
Barbitone acidDIETHYLBARBITURIC ACID5,5-diethyl-1,3-diazinane-2,4,6-trioneMalona
CHEBI:31252DTXCID802643RefChem:388818200-331-2VeronalVesperalMalonalUronal
Datenbank-Bezeichner
- CAS
57-44-3- PubChem CID
- 2294
- DTXSID
DTXSID5022643- ChEMBL
CHEMBL444- ChEBI
CHEBI:31252- UNII
- 5WZ53ENE2P
- EC Number
- 200-331-2
- Nikkaji
- J2.326D
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 75,3 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 247
Experimentelle und physikochemische Eigenschaften
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Barbiturates
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
SpringerMaterials PropertiesCrystal structure
LogP0.71
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Dissociation Constants8.14 (at 15 °C)
Collision Cross Section145.28 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 188 · 188-192°C
- Siedepunkt
- 318.14 °C · 318.14°C (rough estimate)
- Dichte
- 1.22 · 1.2200
- Brechungsindex
- 1.42 · 1.4200 (estimate)
- Flammpunkt
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 7.43 · 7.43(at 25℃)
- Farbe
- 2 O; · Faintly bitter crystals from H2O; polymorphicforms; triagonal crystals, monoclinic prisms, monoclinicneedles, and triclinic cryst
- Wasserlöslichkeit
- 7.149 g/L · 7.149g/L(25 ºC)
- Merck
- 13 · 13,965
- Major Application
- forensics and toxicologypharmaceutical (small molecule)veterinary
- InChI
- 1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
- InChIKey
- FTOAOBMCPZCFFF-UHFFFAOYSA-N
- SMILES
- CCC1(CC)C(=O)NC(=O)NC1=O
- EPA chemische Informationen
- 5 · 5,5-Diethylbarbituric acid (57-44-3)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
DEA schedule IV controlled substance
Status: Active Update: 26-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17765
Barbitone: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5-diethyl-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 1230 3/PG 2
- RTECS-Nr.
- CQ3500000
- risk_code
- 22-39/23/24/25-23/24/25-11-63-40-20
- Toxizität
- LDLo orl-cat: 280 mg/kg PHREA7 19,472,39
- hazard_code
- Xn,T,F
- safety_code
- 36-45-36/37-16-7
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
- DEA Controlled Substances
- CSCN: 2145CSA SCH: Schedule IVNARC: No
Chemie und Industrie
Pharmakologische Informationen
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
Verwendung und Herstellung
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Anwendungen
BeschreibungDie 5,5-Diethylbarbitursäure bildet farb- und geruchlose Blättchen mit schwach bitterem Geschmack. Die Darstellung nach der obigen Vorschrift gelang erstmals 1906 den deutschen Chemikern Joseph Freiherr von Mehring, Emil Fischer und Alfred Dilthey. Das Pr
BeschreibungBarbital is an analytical reference material that is categorized as a barbiturate. It acts as an agonist at GABAA receptors to induce central nervous system depression. Formulations containing barbital have been used as a sedative to treat insomnia and seizures in human and veterinary medicine. Barbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.
VerwendenPrototype of the barbiturate hypnotics.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Ergänzende Hinweise
DefinitionChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).
Zugehörige Reaktionen
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