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

• ChemBase ID: 1179
• Molecular Formular: C11H18N2O3
• Molecular Mass: 226.27222
• Monoisotopic Mass: 226.13174245
• SMILES: O=C1NC(=O)NC(=O)C1(CCC(C)C)CC
• Canonical SMILES: CCC1(CCC(C)C)C(=O)NC(=O)NC1=O
• InChI: InChI=1S/C11H18N2O3/c1-4-11(6-5-7(2)3)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)
• InChIKey: VIROVYVQCGLCII-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: talamo
• Brand Name: Isomytal
• Synonyms: 5-Ethyl-5-(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione; 5-Ethyl-5-isopentylbarbituric Acid; 5-Isoamyl-5-ethylbarbituric Acid; Amal; Amital; Amobarbitone; Amospan; Amybal; Amylbarbitone; Amylobarbital; Amytal; Barbamyl Acid; Binoctal; Dorlotyn; Ethylisopentylbarbituric Acid; Eunoctal; Isopentobarbital; Mylodorm; Pentymal; Robarb; Schiwanox; Sednotic; Somnal; Sumital; NSC 10815; NSC 32406; Amobarbital

Database IDs

• CAS Number: 57-43-2
• PubChem SID: 46508165; 160964641
• PubChem CID: 2164
• CHEBI ID: 2673
• ATC CODE: N05CA02
• CHEMBL: 267894
• Chemspider ID: 2079
• DrugBank ID: DB01351
• KEGG ID: D00555
• Unique Ingredient Identifier: GWH6IJ239E
• Wikipedia Title: Amobarbital

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.484748
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8928068
• LogD (pH = 7.4): 1.8593216
• Log P: 1.8932513
• Molar Refractivity: 58.0029 cm^3
• Polarizability: 22.809618 Å^3
• Polar Surface Area: 75.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.87
• LOG S: -2.4
• Solubility (Water): 8.97e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.07 [HANSCH,C ET AL. (1995)]

Pharmacology Properties

• Admin Routes: Oral, IM, IV, Rectal
• Excretion: Renal
• Half Life: 8-42 hours
• Metabolism: Hepatic
• Legal Status: Schedule II/Schedule III (US); Schedule IV (Canada)

DETAILS

DrugBank - DB01351

• Drug Groups: illicit; approved
• Description: A barbiturate with hypnotic and sedative properties (but not antianxiety). Adverse effects are mainly a consequence of dose-related CNS depression and the risk of dependence with continued use is high. (From Martindale, The Extra Pharmacopoeia, 30th ed, p565)
• References: Kim HS, Wan X, Mathers DA, Puil E: Selective GABA-receptor actions of amobarbital on thalamic neurons. Br J Pharmacol. 2004 Oct;143(4):485-94. Epub 2004 Sep 20. [Pubmed] ; Maynert EW: The alcoholic metabolites of pentobarbital and amobarbital in man. J Pharmacol Exp Ther. 1965 Oct;150(1):118-21. [Pubmed] ; Tang BK, Kalow W, Grey AA: Amobarbital metabolism in man: N-glucoside formation. Res Commun Chem Pathol Pharmacol. 1978 Jul;21(1):45-53. [Pubmed] ; Soine PJ, Soine WH: High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine. J Chromatogr. 1987 Nov 27;422:309-14. [Pubmed] ; McCall WV: The addition of intravenous caffeine during an amobarbital interview. J Psychiatry Neurosci. 1992 Nov;17(5):195-7. [Pubmed]
• External Links: Wikipedia

Toronto Research Chemicals - A634100

Sedative, hypnotic.Controlled substance (depressant).

REFERENCES

• McCall WV: The addition of intravenous caffeine during an amobarbital interview. J Psychiatry Neurosci. 1992 Nov;17(5):195-7. Pubmed
• Kim HS, Wan X, Mathers DA, Puil E: Selective GABA-receptor actions of amobarbital on thalamic neurons. Br J Pharmacol. 2004 Oct;143(4):485-94. Epub 2004 Sep 20. Pubmed
• Maynert EW: The alcoholic metabolites of pentobarbital and amobarbital in man. J Pharmacol Exp Ther. 1965 Oct;150(1):118-21. Pubmed
• Tang BK, Kalow W, Grey AA: Amobarbital metabolism in man: N-glucoside formation. Res Commun Chem Pathol Pharmacol. 1978 Jul;21(1):45-53. Pubmed
• Soine PJ, Soine WH: High-performance liquid chromatographic determination of the diastereomers of 1-(beta-D-glucopyranosyl)amobarbital in urine. J Chromatogr. 1987 Nov 27;422:309-14. Pubmed
• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Licata, S., et al.: Neuropharmacol., 58, 357 (2009)
• Fourches, D., et al.: Chem. Res. Toxicol., 23, 171 (2009)