5-(prop-2-en-1-yl)-5-(propan-2-yl)-1,3-diazinane-2,4,6-trione

• ChemBase ID: 1180
• Molecular Formular: C10H14N2O3
• Molecular Mass: 210.22976
• Monoisotopic Mass: 210.10044232
• SMILES: CC(C)C1(CC=C)C(=O)NC(=O)NC1=O
• Canonical SMILES: C=CCC1(C(C)C)C(=O)NC(=O)NC1=O
• InChI: InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)
• InChIKey: UORJNBVJVRLXMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(prop-2-en-1-yl)-5-(propan-2-yl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: aprobarbital
• Synonyms: 5-(1-Methylethyl)-5-(2-propen-1-yl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Allyl-5-isopropylbarbituric Acid; 5-Isopropyl-5-allylbarbituric acid; Allional; Allonal; Allylisopropylmalonylurea; Allylpropymal; Allypropymal; Alurate; Aprobarbitone; Aprozal; Isopropylallylbarbituric acid; NSC 120769; Numal; Aprobarbital

Database IDs

• CAS Number: 77-02-1
• PubChem SID: 46504558; 160964642
• PubChem CID: 6464

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.478869
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1442441
• LogD (pH = 7.4): 1.1103207
• Log P: 1.1446946
• Molar Refractivity: 53.446 cm^3
• Polarizability: 20.732887 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.24
• LOG S: -1.61
• Solubility (Water): 5.17e+00 g/l

PROPERTIES

Physical Property

• Solubility: 4.08 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]
• Hydrophobicity(logP): 1.15 [HANSCH,C ET AL. (1995)]

DETAILS

DrugBank - DB01352

• Drug Groups: illicit; approved
• Description: Aprobarbital is a barbiturate derivative synthesized in the 1920s by Ernst Preiswerk. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia. Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed.
• External Links: Wikipedia

Toronto Research Chemicals - A735400

Controlled substance (depressant). Sedative, hypnotic.

REFERENCES

• Frey, H.H., et al.: Arzneim. Forsch., 12, 389 (1962)
• Turner, J., et al.: Pharm. Res., 21, 68 (1962)
• Votano, J., et al.: J. Med. Chem., 49, 7169 (1962)