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CHEB

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(Redirected from 5-(2-Cyclohexylideneethyl)-5-ethylbarbituric acid) Convulsant barbiturate
CHEB
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
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)
SMILES
  • CCC1(C(=O)NC(=O)NC1=O)CC=C2CCCCC2
Properties
Chemical formula C14H20N2O3
Molar mass 264.325 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
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.

In low doses, CHEB can block the action of glycine, thus operating in a strychnine similar way.

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.

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.

See also

References

  1. "5-(2-Cyclohexylidene-ethyl)-5-ethylbarbiturate".
  2. 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.
  3. 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.
  4. 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.
  5. 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.
Convulsants
GABA receptor antagonists
GABA synthesis inhibitors
Glycine receptor antagonists
Glutamate receptor agonists
Convulsant barbiturates
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