| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-06 15:16:49 UTC |
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| Update Date | 2020-02-26 21:39:32 UTC |
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| HMDB ID | HMDB0014382 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Butabarbital |
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| Description | Butabarbital, also known as butisol or butabarbitone, belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. Butabarbital is a drug which is used for short-term treatment of insomnia and anxiety disorders. Butabarbital is a very weakly acidic compound (based on its pKa). Butabarbital is a potentially toxic compound. They cause slurred speech, disorientation and "drunken" behavior. Signs of overdose include confusion (severe), decrease in or loss of reflexes, drowsiness (severe), fever, irritability (continuing), low body temperature, poor judgment, shortness of breath or slow or troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness (severe). It belongs to a group of medicines called central nervous system (CNS) depressants that induce drowsiness and relieve tension or nervousness. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). |
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| Structure | |
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| Synonyms | | Value | Source |
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| 5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrione | ChEBI | | 5-Ethyl-5-(1-methylpropyl)barbituric acid | ChEBI | | 5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione | ChEBI | | 5-Sec-butyl-5-ethylbarbituric acid | ChEBI | | 5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trione | ChEBI | | Butisol | ChEBI | | Secbutabarbital | ChEBI | | 5-Ethyl-5-(1-methylpropyl)barbitate | Generator | | 5-Ethyl-5-(1-methylpropyl)barbitic acid | Generator | | 5-Sec-butyl-5-ethylbarbitate | Generator | | 5-Sec-butyl-5-ethylbarbitic acid | Generator | | Butabarbitone | HMDB | | Butrate | HMDB | | Secbubarbital | HMDB | | Secbutobarbital | HMDB | | Secbutobarbitone | HMDB | | Sodium butabarbital | HMDB | | Secumalum | HMDB | | 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, monosodium salt | HMDB | | Butisol sodium | HMDB | | Wallace brand OF butabarbital sodium | HMDB | | Butabarbital sodium | HMDB | | Secbutabarbital sodium | HMDB | | Halsey drug brand OF butabarbital sodium | HMDB | | Sarisol | HMDB |
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| Chemical Formula | C10H16N2O3 |
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| Average Molecular Weight | 212.2456 |
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| Monoisotopic Molecular Weight | 212.116092388 |
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| IUPAC Name | 5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione |
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| Traditional Name | butabarbital |
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| CAS Registry Number | 125-40-6 |
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| SMILES | CCC(C)C1(CC)C(=O)NC(=O)NC1=O |
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| InChI Identifier | InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15) |
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| InChI Key | ZRIHAIZYIMGOAB-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Diazines |
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| Sub Class | Pyrimidines and pyrimidine derivatives |
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| Direct Parent | Barbituric acid derivatives |
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| Alternative Parents | |
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| Substituents | - Barbiturate
- N-acyl urea
- Ureide
- 1,3-diazinane
- Dicarboximide
- Urea
- Carbonic acid derivative
- Carboxylic acid derivative
- Azacycle
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Physiological effect | Health effect: |
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| Disposition | Biological location: |
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| Role | Industrial application: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 166.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 1.39 g/L | Not Available | | LogP | 1.5 | Not Available |
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| Predicted Properties | |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a7i-8900000000-fc5f17ec8979e31b77ac | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-1290000000-73748d3c96bdcbc7692d | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0007-3900000000-c62b6d06318be5ee7a26 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-9000000000-d815b39070a4a2b620ee | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0296-8950000000-e8d3b0ea461e5ad69068 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-9500000000-43d75b9170cae3f239fa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-000x-9400000000-ec7399384bd48aaa6ee4 | Spectrum | | MS | Mass Spectrum (Electron Ionization) | splash10-0a4l-6900000000-6e0cbc3d26c5541ad8eb | Spectrum |
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