Basic information
- CAS
77-28-1- Standard SMILES
CCCCC1(CC)C(=O)NC(=O)NC1=O- InChIKey
STDBAQMTJLUMFW-UHFFFAOYSA-N- Molecular formula
- C10H16N2O3
- Average molar mass
- 212.25 g/mol
- Monoisotopic mass
- 212.11609238
Overview
Butobarbital is a member of barbiturates.
Names & identifiers
- Preferred name
- Butobarbital
- IUPAC
- 5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
- English name
- BUTETHAL--DEA SCHEDULE III ITEM
- Molecular formula
- C10H16N2O3
- Molecular weight
- 212.25
Names & synonyms
ButethalButobarbitalButobarbitoneButobarbituralSonerylNeonalButobarbitalum5-BUTYL-5-ETHYLBARBITURIC ACID77-28-15-Ethyl-5-n-butylbarbituric acid5-Ethyl-5-butylbarbituric acid5-butyl-5-ethyl-1,3-diazinane-2,4,6-trione
Show more names
BudormEtovalMeonalMonodormSonerileLonganoctHyperbutal
5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneOHZ8QAW6YCNSC-229336DTXSID70227808butethal, monosodium saltRefChem:122147DTXCID80150299201-019-9
Database identifiers
- CAS
77-28-1- PubChem CID
- 6473
- DTXSID
DTXSID70227808- ChEMBL
CHEMBL404422- ChEBI
CHEBI:134884- UNII
- OHZ8QAW6YC
- EC Number
- 201-019-9
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 75.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 279
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Barbiturates
Pharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP
1.73
1.73
Solubility1.27e+00 g/L
Melting Point128.5 °C
Physical DescriptionSolid
Dissociation Constants7.86
Physicochemical properties
- Melting point
- 124 · 124-127°
- Boiling point
- 352.08 °C · 352.08°C (rough estimate)
- Density
- 1.1718 · 1.1718 (rough estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (97.4%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-butyl-5-ethyl-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (97.4%)
Toxicology
Health EffectsThey cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive. They cause slurred speech, disorientation and "drunken" behavior. They are physically and psychologically addictive.
Exposure RoutesRapidly absorbed following oral administration. Parenteral (intraperitroneal injection or infusion).
Toxicity Summary
Butethal binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Butethal (also known as butobarbitone and butobarbital) belongs to a group of medicines called the barbiturates. It is thought to act on receptors in the brain (GABA receptors) causing the release of the chemical GABA. This chemical inhibits certain areas of the brain resulting in sleepiness.
Mechanism of Action
Butethal binds at a distinct binding site associated with a Cl<sup>-</sup> ionopore at the GABA<sub>A</sub> receptor, increasing the duration of time for which the Cl<sup>-</sup> ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.
Biological Half-Life37 hours
Metabolism/Metabolites
Hepatic.
Hepatic. Half Life: 37 hours
MeSH Pharmacological ClassificationDrugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Absorption, Distribution and ExcretionRapidly absorbed following oral administration.
Cellular LocationsMembrane
Uses & manufacturing
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…