5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 122
• Molecular Formular: C10H16N2O3
• Molecular Mass: 212.24564
• Monoisotopic Mass: 212.11609238
• SMILES: O=C1NC(=O)NC(=O)C1(C(CC)C)CC
• Canonical SMILES: CCC(C1(CC)C(=O)NC(=O)NC1=O)C
• InChI: InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
• InChIKey: ZRIHAIZYIMGOAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: butabarbital
• Brand Name: Butabarb; Butalan; Butatab; Butatal; Buticaps; Butisol; Butisol Sodium; Medarsed; Nilox; Sarisol; Sarisol No. 1; Unicelles
• Synonyms: 5-sec-Butyl-5-ethylbarbituric Acid; Butabarb; Butatab; Butatal; Medarsed; NSC 27517; Nilox; Unicelles; sec-Butobarbitone; 5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-sec-Butyl-5-ethyl-Barbituric Acid; Butabarbital Sodium; Butabarbitone; Secbubarbital; Secbutobarbitone; Secbutobarbital; Secbutabarbital; Sodium Butabarbital; Butrate; Butabarbital; Butabarbital; Butisol

Database IDs

• CAS Number: 125-40-6
• PubChem SID: 46505051; 160963585
• PubChem CID: 2479
• CHEBI ID: 3228
• CHEMBL: 449
• Chemspider ID: 2385
• DrugBank ID: DB00237
• KEGG ID: D03180
• Unique Ingredient Identifier: P0078O25A9
• Wikipedia Title: Butabarbital
• Medline Plus: a682417

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.482024
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.4482353
• LogD (pH = 7.4): 1.4145478
• Log P: 1.4486825
• Molar Refractivity: 53.4019 cm^3
• Polarizability: 20.98239 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.7
• LOG S: -2.18
• Solubility (Water): 1.39e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1360 mg/L
• Hydrophobicity(logP): 1.5

Pharmacology Properties

• Half Life: 100 hours
• Legal Status: Schedule III (Canada); Schedule III (US)

DETAILS

DrugBank - DB00237

• Drug Groups: illicit; approved
• Description: Butabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia]
• Indication: For short-term treatment of insomnia and anxiety disorders
• Pharmacology: Butabarbital, a barbiturate, is used for the treatment of short term insomnia. It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Little analgesia is conferred by barbiturates; their use in the presence of pain may result in excitation.
• 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
• Elimination: Barbiturates are metabolized primarily by the hepatic microsomal enzyme system, and most metabolic products are excreted in the urine.
• External Links: Wikipedia; Drugs.com

Toronto Research Chemicals - B689920

Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

• Heller, D., et al.: J. Agric. Food Chem., 49, 4597 (2001)
• Ramirez, A., et al.: Anal. Chem., 79, 3155 (2001)