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.
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-5-ethylbarbituric_acid_(3d).png)
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| Names | |
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| IUPAC name
5-ethyl-5-(4-methylpentan-2-yl)-1,3-diazinane-2,4,6-trione
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Other names
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| 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).
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Pharmacology
editDiberal, 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),[2] 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.[3]
(+)-Isomer
edit(+)-DMBB is the atypical enantiomer of diberal. It is atypical in the means that it has convulsant action, unlike most barbiturate drugs.[4]
(−)-Isomer
editUnlike (+)-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.[3] (−)-DMBB is slightly more potent than pentobarbital in its depressant properties.[5]
References
edit- ^ "Diberal". PubChem. U.S. National Library of Medicine.
- ^ Suddock JT, Kent KJ, Regina AC, Cain MD (2024). "Barbiturate Toxicity". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 29763050.
- ^ a b Ho IK, Harris RA (1981). "Mechanism of action of barbiturates" (PDF). Annual Review of Pharmacology and Toxicology. 21: 83–111. doi:10.1146/annurev.pa.21.040181.000503. PMID 6263177.
- ^ Desai R, Savechenkov PY, Zolkowska D, Ge RL, Rogawski MA, Bruzik KS, et al. (November 2015). "Contrasting actions of a convulsant barbiturate and its anticonvulsant enantiomer on the α1 β3 γ2L GABAA receptor account for their in vivo effects". The Journal of Physiology. 593 (22): 4943–4961. doi:10.1113/JP270971. PMC 4650410. PMID 26378885.
- ^ Downes H, Perry RS, Ostlund RE, Karler R (December 1970). "A study of the excitatory effects of barbiturates". The Journal of Pharmacology and Experimental Therapeutics. 175 (3): 692–699. PMID 5489924.