Basic information
- Standard SMILES
CCC1(CC)C(=O)NC(=O)NC1=O- InChIKey
FTOAOBMCPZCFFF-UHFFFAOYSA-N- Molecular formula
- C8H12N2O3
- Average molar mass
- 184.19 g/mol
- Monoisotopic mass
- 184.08479224
Overview
5,5-diethylbarbituric acid is a member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid). It has a role as a drug allergen.
Names & identifiers
- Preferred name
- Barbital
- IUPAC
- 5,5-diethyl-1,3-diazinane-2,4,6-trione
- English name
- BARBITAL
- Molecular formula
- C8H12N2O3
- Molecular weight
- 184.19
Names & synonyms
barbitalBarbitone5,5-Diethylbarbituric acid57-44-3DiethylmalonylureaEthylbarbitalDiemalDEBADTXSID50226435,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione5WZ53ENE2PNSC-31352
Show more names
Barbitone acidDIETHYLBARBITURIC ACID5,5-diethyl-1,3-diazinane-2,4,6-trioneMalona
CHEBI:31252DTXCID802643RefChem:388818200-331-2VeronalVesperalMalonalUronal
Database identifiers
- CAS
57-44-3- PubChem CID
- 2294
- DTXSID
DTXSID5022643- ChEMBL
CHEMBL444- ChEBI
CHEBI:31252- UNII
- 5WZ53ENE2P
- EC Number
- 200-331-2
- Nikkaji
- J2.326D
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 75.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 247
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Depressants and Tranquilizers
DEA Schedule IV Controlled Substance -> Depressants
Pharmaceuticals -> Barbiturates
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
SpringerMaterials PropertiesCrystal structure
LogP0.71
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Dissociation Constants8.14 (at 15 °C)
Collision Cross Section145.28 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 188 · 188-192°C
- Boiling point
- 318.14 °C · 318.14°C (rough estimate)
- Density
- 1.22 · 1.2200
- refractive index
- 1.42 · 1.4200 (estimate)
- Flash point
- 11 °C · 11 °C
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 7.43 · 7.43(at 25℃)
- color
- 2 O; · Faintly bitter crystals from H2O; polymorphicforms; triagonal crystals, monoclinic prisms, monoclinicneedles, and triclinic cryst
- Water Solubility
- 7.149 g/L · 7.149g/L(25 ºC)
- Merck
- 13 · 13,965
- Major Application
- forensics and toxicologypharmaceutical (small molecule)veterinary
- InChI
- 1S/C8H12N2O3/c1-3-8(4-2)5(11)9-7(13)10-6(8)12/h3-4H2,1-2H3,(H2,9,10,11,12,13)
- InChIKey
- FTOAOBMCPZCFFF-UHFFFAOYSA-N
- SMILES
- CCC1(CC)C(=O)NC(=O)NC1=O
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 5 WZ53ENE2P · 5WZ53ENE2P
- ATC code
- 5 CA04 · N05CA04
- EPA Substance Registry System
- 5 · 5,5-Diethylbarbituric acid (57-44-3)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 264 · P264-P270-P301+P312-P330-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn,T,F
- Risk Statements
- 22 · 22-39/23/24/25-23/24/25-11-63-40-20
- Safety Statements
- 36 · 36-45-36/37-16-7
- RIDADR
- 1230 · UN 1230 3/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 3500000 · CQ3500000
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- Toxicity
- 280 mg/kg · LDLo orl-cat: 280 mg/kg PHREA7 19,472,39
- DEA Controlled Substances
- 2145 CSA · CSCN: 2145CSA SCH: Schedule IVNARC: No
- REACH Registrations
- Active
Safety & regulation
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 40 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
DEA schedule IV controlled substance
Status: Active Update: 26-05-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/17765
Barbitone: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 2,4,6(1H,3H,5H)-Pyrimidinetrione, 5,5-diethyl-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- CQ3500000
- ridadr
- UN 1230 3/PG 2
- Toxicity
- LDLo orl-cat: 280 mg/kg PHREA7 19,472,39
- risk_code
- 22-39/23/24/25-23/24/25-11-63-40-20
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T,F
- safety_code
- 36-45-36/37-16-7
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P330-P501
- DEA Controlled Substances
- CSCN: 2145CSA SCH: Schedule IVNARC: No
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
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.
Uses & manufacturing
Use ClassificationPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionBarbital is an analytical reference material that is categorized as a barbiturate. It acts as an agonist at GABAA receptors to induce central nervous system depression. Formulations containing barbital have been used as a sedative to treat insomnia and seizures in human and veterinary medicine. Barbital is regulated as a Schedule IV compound in the United States. This product is intended for research and forensic applications.
DescriptionBarbital (CRM) (Item No. 22854) is a certified reference material categorized as a barbiturate. Barbital is regulated as a Schedule IV compound in the United States. Barbital (CRM) (Item No. 22854) is provided as a DEA exempt preparation. This product is intended for research and forensic applications.
UsesPrototype of the barbiturate hypnotics.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A member of the class of barbiturates, the structure of which is that of barbituric acid substituted at C-5 by two ethyl groups. Formerly used as a hypnotic (sleeping aid).
Related reactions
7 records
Linked notes
Loading…