CHEB

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

CAS Number

* 22173-64-4

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL44981

ChemSpider |

* 28727

PubChem CID

* 30964

UNII |

* BTE6MU3YBG

CompTox Dashboard (EPA)

* DTXSID60176710

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−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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

[edit]

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

[edit]

* Diberal (DMBB)
* McN-481

## References

[edit]

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.

* v
* t
* e

Convulsants

GABA receptor antagonists|

* Bicuculline
* Bicyclic phosphates (TBPS, TBPO, IPTBO)
* BIDN
* Chlorophenylsilatrane
* Cicutoxin
* Cloflubicyne
* Coriamyrtin
* Dihydropicrotoxinin
* DMCM
* EBOB
* Endosulfan
* FG-7142
* Fipronil
* Flurothyl
* Gabazine
* Oenanthotoxin
* Pentylenetetrazol
* Phenylsilatrane
* Picrotoxin
* p-CN-TBOB
* p-NCS-TBOB
* RDX
* TBOB
* Tetramethylenedisulfotetramine
* Thujone
* Trimethylolpropane phosphite
* Tutin

GABA synthesis inhibitors|

* 3-Mercaptopropionic acid
* 4-Deoxypyridoxine
* Allylglycine
* Crimidine
* Decaborane
* Ginkgotoxin
* Isoniazid
* Pentaborane
* Thiocarbohydrazide
* Toxopyrimidine

Glycine receptor antagonists|

* Coriamyrtin
* Dendrobine
* Picrotoxin
* Strychnine
* Tutin

Glutamate receptor agonists|

* AMPA
* Domoic acid
* Kainic acid
* NMDA
* Quisqualic acid
* Tetrazolylglycine

Convulsant barbiturates|

* CHEB
* Diberal (DMBB)
* McN-481

Other|

* 2,2,3,3-Tetrafluoropropyl trifluoromethyl ether
* Bromocamphor
* Camphor
* FAZ-4
* Fluoroethyl fluoroacetate
* MC-2973
* Methionine sulfoximine
* Methyl fluoroacetate
* Nitrocyclohexane
* Thebaine

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
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