Eterobarb

Eterobarb

Systematic (IUPAC) name
5-ethyl-1,3-bis(methoxymethyl)-5-phenyl-1,3-diazinane-2,4,6-trione
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	27511-99-5
ATC code	None
PubChem	CID 33925
ChemSpider	31271
UNII	432SI047GA
KEGG	D04077
Chemical data
Formula	C16H20N2O5
Molar mass	320.340 g/mol
SMILES CCC1(C(=O)N(C(=O)N(C1=O)COC)COC)C2=CC=CC=C2
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 Key:DACOQFZGGLCXMA-UHFFFAOYSA-N
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Eterobarb (Antilon) is a barbiturate derivative. It has mainly anticonvulsant action with less sedative effects than the closely related compound phenobarbital. It saw reasonable success in clinical trials, but is not in widespread medical use.^[1][2]

Synthesis

Eterobarb can be synthesized by reacting phenobarbital with chloromethyl methyl ether in presence of a base.^[3]

Eterobarb synthesis

References

1. Gallagher, BB; Baumel, IP; Woodbury, SG; Dimicco, JA (1975). "Clinical evaluation of eterobarb, a new anticonvulsant drug". Neurology 25 (5): 399–404. doi:10.1212/wnl.25.5.399. PMID 1094318.
2. Smith, DB; Goldstein, SG; Roomet, A (1986). "A comparison of the toxicity effects of the anticonvulsant eterobarb (antilon, DMMP) and phenobarbital in normal human volunteers". Epilepsia 27 (2): 149–55. doi:10.1111/j.1528-1157.1986.tb03518.x. PMID 3956454.
3. Vida, Julius A. (1971). "Anticonvulsants. 1. Alkoxymethyl derivatives of barbiturates and diphenylhydantoin". Journal of Medicinal Chemistry 14 (3): 187–189. doi:10.1021/jm00285a002.