5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione

• ChemBase ID: 127314
• Molecular Formular: C16H20N2O5
• Molecular Mass: 320.3404
• Monoisotopic Mass: 320.13722175
• SMILES: O=C1N(C(=O)N(C(=O)C1(c1ccccc1)CC)COC)COC
• Canonical SMILES: CCC1(c2ccccc2)C(=O)N(COC)C(=O)N(C1=O)COC
• InChI: InChI=1S/C16H20N2O5/c1-4-16(12-8-6-5-7-9-12)13(19)17(10-22-2)15(21)18(11-23-3)14(16)20/h5-9H,4,10-11H2,1-3H3
• InChIKey: DACOQFZGGLCXMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
• IUPAC Traditional name: antilon; 5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
• Synonyms: Eterobarb; 5-Ethyl-1,3-bis(methoxymethyl)-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione; 1,3-Bis(methoxymethyl)-5-ethyl-5-phenylbarbituric acid; 1,3-Bis(methoxymethyl)phenobarbital; Antilon; Eterobarb; N,N'-Bis(methoxymethyl)phenobarbital; RMI 16238; Eterobarbital; Dimethoxymethylphenobarbital; Eterobarb

Database IDs

• CAS Number: 27511-99-5
• PubChem SID: 162221635
• PubChem CID: 33925
• Chemspider ID: 31271
• KEGG ID: D04077
• Unique Ingredient Identifier: 432SI047GA
• Wikipedia Title: Eterobarb

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.9799331
• LogD (pH = 7.4): 1.9799331
• Log P: 1.9799331
• Molar Refractivity: 81.2457 cm^3
• Polarizability: 31.95902 Å^3
• Polar Surface Area: 76.15 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 116-118°C

Pharmacology Properties

• Admin Routes: Oral
• Mechanism of Action: Produces all levels of CNS mood alteration

Product Information

• Application(s): Anticonvulsant; Sedative

DETAILS

Toronto Research Chemicals - E675000

Controlled substance (depressant).An alkoxymethyl derivative of Phenobarbital, reported to have little or no hypnotic activity. Anticonvulsant.

REFERENCES

• Samour, C.M., et al.: J. Med. Chem., 14, 187 (1971)
• Vida, J.A., et al.: J. Med. Chem., 16, 602 (1971)
• Gal, J., et al.: Pharm. Sci., 68, 1562 (1971)
• Goldberg, M.A., et al.: Ann. Neurol., 5, 121 (1971)
• Rising, M. et al., J.A.C.S., 1918, 40, 723, (synth)
• Grtzmacher, H.F. et al., Tet. Lett., 1966, 1365, (ms)
• Vida, J.A. et al., J. Med. Chem., 1971, 14, 187, (synth, pharmacol, Eterobarb)
• Williams, P.P., Acta Cryst. B, 1973, 29, 1572, (cryst struct)
• Long, R.C. Jr. et al., J. Magn. Reson., 1974, 16, 228, (cmr)
• Voronin, V.G. et al., Khim. Geterotsikl. Soedin., 1975, 1431; 1978, 813, (synth, ms)
• IARC Monog., 1977, 13, 157; Suppl. 6, 455; Suppl. 7, 313, (rev, tox)
• Chao, M.K.C. et al., Anal. Profiles Drug Subst., 1978, 7, 359, (rev)
• Prichard, J.W., Adv. Neurol., 1980, 27, 473; 493; 501; 553,, (revs)
• Rautio, M. et al., Org. Magn. Reson., 1981, 15, 53, (pmr, cmr)
• Buchet. R. et al., Spectrochim. Acta A, 1982, 38, 239, (ir, Raman)
• Kopinski, R.P. et al., Aust. J. Chem., 1984, 37, 1245, (synth)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 2266, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 301; 302
• Antiepileptic Drugs, (Eds. Levy, R.H. et al), 4th edn., Raven Press, 1995
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BDS300; CPO500; EOK000; SID000