5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 1181
• Molecular Formular: C10H16N2O3
• Molecular Mass: 212.24564
• Monoisotopic Mass: 212.11609238
• SMILES: O=C1NC(=O)NC(=O)C1(CCCC)CC
• Canonical SMILES: CCCCC1(CC)C(=O)NC(=O)NC1=O
• InChI: InChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)
• InChIKey: STDBAQMTJLUMFW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: butethal
• Brand Name: Etoval; Hyperbutal; Longanoct; Meonal; Monodorm; Neonal; Sonerile; Soneryl; Budorm
• Synonyms: Butethal; 5-n-Butyl-5-ethylbarbituric Acid; Budorm; Etoval; Hyperbutal; Longanoct; Monodorm; NSC 229336; Neonal; Sonerile; Soneryl; Butobarbital; Butobarbital; 5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Butyl-5-ethylbarbituric acid; Butobarbitone; 5-Ethyl-5-butylbarbituric acid; 5-Ethyl-5-N-butylbarbituric acid; Butabarbitol; Butobarbitalum; Butobarbitural; Butyl,5-ethylbarbituric acid; Butethal

Database IDs

• CAS Number: 77-28-1
• PubChem SID: 160964643; 46508397
• PubChem CID: 6473

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.48475
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6057878
• LogD (pH = 7.4): 1.5723026
• Log P: 1.6062322
• Molar Refractivity: 53.4543 cm^3
• Polarizability: 20.98239 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.65
• LOG S: -2.22
• Solubility (Water): 1.27e+00 g/l

PROPERTIES

Physical Property

• Solubility: 4.88 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 1.73 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01353

• Drug Groups: illicit; approved
• Description: Butethal is a sedative and a hypnotic drug.
• Indication: For the treatment of insomnia.
• Pharmacology: Butethal (also known as butobarbitone and butobarbital) belongs to a group of medicines called the barbiturates. It is thought to act on receptors in the brain (GABA receptors) causing the release of the chemical GABA. This chemical inhibits certain areas of the brain resulting in sleepiness.
• Toxicity: Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed following oral administration.
• Half Life: 37 hours
• External Links: Wikipedia

Toronto Research Chemicals - B690105

Butobarbital is a barbiturate derivative that is used as a hypnotic agent with sedative and anticonvulsant properties. Butobarbital is a Controlled Substance.

REFERENCES

• Sitsen, J.M.A. et al.: Pharmac. Week., 109, 1 (1974)
• Adams, R.G.: Psychopharmacologia, 40, 185 (1974)