Convulsant barbiturate
CHEB[1]
Names
IUPAC name
5-(2-cyclohexylideneethyl)-5-ethyl-1,3-diazinane-2,4,6-trione
Other names
CHEB 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)
CCC1(C(=O)NC(=O)NC1=O)CC=C2CCCCC2
Properties
C 14 H 20 N 2 O 3
Molar mass
264.325 g·mol−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 as BRN 0250312 is a convulsant barbiturate . Its mechanism of action is not fully understood.
Pharmacodynamics
CHEB has uncommon action compared to other barbiturates . While other barbiturates such as Barbital are usually anticonvulsants , CHEB is a convulsant .
CHEB's convulsant action is not fully understood. There may be multiple mechanisms involved in its properties;
In rats, CHEB stimulates the release of glutamate , an excitatory neurotransmitter .[2]
In low doses, CHEB can block the action of glycine , thus operating in a strychnine similar way.[3]
Another study has shown that CHEB could increase the release of acetylcholine . 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 of GABA , this is a strange property, as compounds that enhance GABA binding usually have anticonvulsant action, such as Diazepam .[5]
References
^ "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 .