Basic information
- CAS
50-09-9- Standard SMILES
CN1C(=O)NC(=O)C(C)(C2=CCCCC2)C1=O- InChIKey
UYXAWHWODHRRMR-UHFFFAOYSA-N- Molecular formula
- C12H16N2O3
- Average molar mass
- 236.27 g/mol
- Monoisotopic mass
- 236.11609238
Overview
Hexobarbital is a member of the class of barbiturates taht is barbituric acid substituted at N-1 by methyl and at C-5 by methyl and cyclohex-1-enyl groups. It is functionally related to a barbituric acid.
Names & identifiers
- Preferred name
- Hexobarbital
- IUPAC
- 5-(cyclohexen-1-yl)-1,5-dimethyl-1,3-diazinane-2,4,6-trione
- English name
- HEXOBARBITAL
- Molecular formula
- C12H16N2O3
- Molecular weight
- 236.27
Names & synonyms
HexobarbitalHexobarbitoneMethexenylMethylhexabital56-29-1EvipalEvipanSombucapsSombulexEnhexymalHexobarbitalumHexobarbitonum
Show more names
HexenalDoricoToleranCitodonCitopanCyclopanNarcosan
5-(1-CYCLOHEXEN-1-YL)-1,5-DIMETHYLBARBITURIC ACIDHexobarbital ciiiDTXSID90231225-(1-Cyclohexen-1-yl)-1,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneAL8Z8K3P6SNSC-71929CHEBI:5706DTXCID903122
Database identifiers
- CAS
50-09-9、56-29-1- PubChem CID
- 3608
- DTXSID
DTXSID9023122- ChEMBL
CHEMBL7728- ChEBI
CHEBI:5706- UNII
- AL8Z8K3P6S
- EC Number
- 200-264-9
- Nikkaji
- J1.915A
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 66.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 427
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
Pharmaceuticals -> Barbiturates
LogP
1.98
1.71
Solubility1.51e+00 g/L
Melting Point67.00 °C. @ 760.00 mm Hg
Physical DescriptionSolid
Dissociation Constants8.2
Physicochemical properties
- Melting point
- 145 · 145-147°
- Boiling point
- 378.73 °C · 378.73°C (rough estimate)
- Density
- 1.1623 · 1.1623 (rough estimate)
- refractive index
- 1.546 · 1.5460 (estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 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-(1-cyclohexen-1-yl)-1,5-dimethyl-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
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 RoutesOral
Toxicity Summary
Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Signs and SymptomsSymptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
N - Nervous system
QN - Nervous system
QN - Nervous system
Protein Binding25%
Pharmacodynamics
Hexobarbital is a barbiturate derivative having hypnotic and sedative effects. It was subsequently used in the 1940s and 1950s as an anesthetic for surgery. Furthermore, the agent also demonstrates a fairly quick onset of action that also possesses a short duration of action. However it can be difficult to control the depth of anesthesia with hexobarbital which makes it quite dangerous, and it has now been replaced by safer drugs in human medicine, usually thiopental would be the barbiturate of choice for this application these days.
Mechanism of Action
Hexobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABA-A receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Metabolism/Metabolites
Hepatic.
Hepatic.
MeSH Pharmacological Classification
Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.
Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here.
Cellular LocationsCytoplasm
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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