Convulsant barbiturate
CHEB[ 1] Names IUPAC name 5-(2-Cyclohexylideneethyl)-5-ethyl-1,3-diazinane-2,4,6-trione
Other namesCHEB 5-(2-cyclohexylidene-ethyl)-5-ethyl barbituric acid 5-(2-cyclohexylidene-ethyl)-5-ethyl barbiturate BRN 0250312 Identifiers ChEMBL ChemSpider UNII Key: AVSLJNHOEKBNAF-UHFFFAOYSA-N
InChI=1S/C14H20N2O3/c1-2-14(9-8-10-6-4-3-5-7-10)11(17)15-13(19)16-12(14)18/h8H,2-7,9H2,1H3,(H2,15,16,17,18,19)
Properties C 14 H 20 N 2 O 3 Molar mass −1 Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
CHEB , also known asBRN 0250312 is aconvulsant barbiturate . Its mechanism of action is not fully understood.
CHEB has uncommon action compared to otherbarbiturates . While otherbarbiturates such asBarbital are usuallyanticonvulsants , CHEB is aconvulsant .
CHEB's convulsant action is not fully understood. There may be multiple mechanisms involved in its properties;
In rats, CHEB stimulates the release ofglutamate , an excitatoryneurotransmitter .[ 2]
In low doses, CHEB can block the action ofglycine , thus operating in astrychnine similar way.[ 3]
Another study has shown that CHEB could increase the release ofacetylcholine . This result was not observed with some other convulsants (S(+)-MPPB, pentylenetetrazol and Ro-5-3663), suggesting that this property is unique.[ 4]
Paradoxically, CHEB is able to enhance the binding ofGABA , this is a strange property, as compounds that enhance GABA binding usually haveanticonvulsant action, such asdiazepam .[ 5]
^ "5-(2-Cyclohexylidene-ethyl)-5-ethylbarbiturate" .^ Wei, L.; Schlame, M.; Downes, H.; Hemmings, H. C. (June 1996)."CHEB, a convulsant barbiturate, evokes calcium-dependent spontaneous glutamate release from rat cerebrocortical synaptosomes" .Neuropharmacology .35 (6):695– 701.doi :10.1016/0028-3908(96)84641-7 ISSN 0028-3908 .PMID 8887978 . ^ Nicholson, G. M.; Spence, I.; Johnston, G. A. (June 1985)."Strychnine-like action of the convulsant barbiturate, CHEB" .Neuropharmacology .24 (6):465– 471.doi :10.1016/0028-3908(85)90050-4 .ISSN 0028-3908 .PMID 2862600 .S2CID 31187813 . ^ Holtman, J. R.; Richter, J. A. (September 1983)."Increased release of [3H]acetylcholine in vitro from the mouse hippocampus by a convulsant barbiturate" .Neuropharmacology .22 (9):1101– 1108.doi :10.1016/0028-3908(83)90031-x .ISSN 0028-3908 .PMID 6138729 .S2CID 43453342 . ^ Willow, M; Johnston, GA (1981-04-01)."Enhancement by anesthetic and convulsant barbiturates of GABA binding to rat brain synaptosomal membranes" .The Journal of Neuroscience .1 (4):364– 367.doi :10.1523/JNEUROSCI.01-04-00364.1981 .ISSN 0270-6474 .PMC 6564141 PMID 6267224 .
