5,5-diethyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 1280
• Molecular Formular: C8H12N2O3
• Molecular Mass: 184.19248
• Monoisotopic Mass: 184.08479225
• SMILES: O=C1NC(=O)NC(=O)C1(CC)CC
• Canonical SMILES: CCC1(CC)C(=O)NC(=O)NC1=O
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,5-diethyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: veronal
• Synonyms: 5,5-Diethyl-barbituric Acid; Deba; Diemal; Diethylbarbitone; Diethylbarbituric Acid; Diethylmalonylurea; Dormonal; Ethylbarbital; Hypnogene; Malonal; NSC 31352; Sedeval; Uronal; Veroletten; Veronal Acetate; Vesperal; Barbital; Barbital; 5,5-Diethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5,5-Diethylbarbituric acid; Barbitone; Veronal; 5,5-二乙基-2,4,6(1H,3H,5H)-嘧啶三酮; 5,5-二乙基巴比妥酸; 佛罗拿; 巴比通; 巴比妥

Database IDs

• CAS Number: 57-44-3
• EC Number: 200-331-2
• MDL Number: MFCD00036212
• Beilstein Number: 163999
• PubChem SID: 24891513; 46508979; 160964740; 24859202
• PubChem CID: 2294
• CHEBI ID: 31252
• ATC CODE: N05CA04
• CHEMBL: 444
• Chemspider ID: 2206
• DrugBank ID: DB01483
• KEGG ID: D01740
• Unique Ingredient Identifier: 5WZ53ENE2P
• Wikipedia Title: Barbital
• Medline Plus: a682221

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.484852
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.7166505
• LogD (pH = 7.4): 0.6831729
• Log P: 0.71709484
• Molar Refractivity: 44.2523 cm^3
• Polarizability: 17.337637 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.73
• LOG S: -1.76
• Solubility (Water): 3.23e+00 g/l

PROPERTIES

Physical Property

• Solubility: 7.46 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Melting Point: 188-192 °C; 189-191 °C
• Hydrophobicity(logP): 0.65 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: CQ3500000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; Home Office Schedule 3; psychotrope; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada; USDEA Schedule IV; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 30.3 (± 3.2) hours
• Legal Status: Schedule IV (US)

Product Information

• Purity: ≥98.0% (T); ≥99.0% (T)
• Grade: purum
• Ignition Residue: ≤0.1% (as SO4)
• Cation Traces: Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤200 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤500 mg/kg; sulfate (SO42-): ≤50 mg/kg
• Loss on Drying: ≤0.5% loss on drying, 20 °C (HV)
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C8H12N2O3

DETAILS

DrugBank - DB01483

• Drug Groups: illicit; experimental
• Description: A long-acting barbiturate that depresses most metabolic processes at high doses. It is used as a hypnotic and sedative and may induce dependence. Barbital is also used in veterinary practice for central nervous system depression. [PubChem]
• External Links: Wikipedia

Sigma Aldrich - B0375

Biochem/physiol Actions
镇静剂/催眠药

Sigma Aldrich - 31995

Biochem/physiol Actions
Sedative/hypnotic
Other Notes
Sales restrictions may apply

Sigma Aldrich - 32000

Biochem/physiol Actions
Sedative/hypnotic
Other Notes
Sales restrictions may apply

Toronto Research Chemicals - B118500

Prototype of the barbiturate hypnotics.

REFERENCES

• Kholod, Y., et al.: Environ. Sci. Technol., 43, 9208 (2009)
• Yu, J., et al.: Pharm. Res., 27, 457 (2009)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)