CHEB

Last updated
CHEB [1]
CHEB structure.png
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
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
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
C14H20N2O3
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).

CHEB, also known as BRN 0250312 is a convulsant barbiturate. Its mechanism of action is not fully understood.

Contents

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]

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.
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