Diberal

Diberal

File:DMBB structure.png
File:5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid (3d).png
Names
IUPAC name 5-ethyl-5-(4-methylpentan-2-yl)-1,3-diazinane-2,4,6-trione
Other names DMBB 5-Ethyl-5-(1,3-dimethylbutyl)barbituric acid 5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid
Identifiers
CAS Number	2964-06-9
3D model (JSmol)	Interactive image
ChemSpider	17079
ECHA InfoCard
E number
PubChem CID	18079
UNII	31E1HC8I46
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C12H20N2O3/c1-5-12(8(4)6-7(2)3)9(15)13-11(17)14-10(12)16/h7-8H,5-6H2,1-4H3,(H2,13,14,15,16,17) Key: KXHLANWWTKSOMW-UHFFFAOYSA-N
SMILES CCC1(C(=O)NC(=O)NC1=O)C(C)CC(C)C
Properties
Chemical formula	C12H20N2O3
Molar mass	240.303 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

Diberal, also known as 5-(1,3-Dimethylbutyl)-5-ethylbarbituric acid or DMBB, is an atypical barbiturate. This compound can be either convulsant or anticonvulsant depending on which enantiomer is used.

Pharmacology

Diberal, unlike most barbiturates, can have convulsant actions. This is uncommon, as barbiturates typically enhance the function of GABA as allorestic modulators and agonists (at higher doses), therefore having anticonvulsant properties. Depending on which isomer is used, it can have either convulsant or anticonvulsant actions.

The different pharmacological profile between isomers is thought to be due to the differences in the formation of hydrogen bonds at the binding sites.

(+)-Isomer

(+)-DMBB is the atypical enantiomer of diberal. It is atypical in the means that it has convulsant action, unlike most barbiturate drugs.

(−)-Isomer

Unlike (+)-DMBB, the (−)-isomer is similar to most barbiturates by having anticonvulsant action. It has been found that administration of (−)-DMBB reverses the convulsant actions of (+)-DMBB. (−)-DMBB is slightly more potent than pentobarbital in its depressant properties.

See also

• CHEB
• McN-481