714-59-0

Basic information

• Product Name: 1,3-dimethylbarbital
• Synonyms: 1,3-dimethylbarbital;1,3-Dimethyl-5,5-diethylbarbituric acid;1,3-Dimethyl-5,5-diethylpyrimidine-2,4,6(1H,3H,5H)-trione;5,5-Diethyl-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione;N,N'-Dimethylbarbital
• CAS NO: 714-59-0
• Molecular Formula: C₁₀H₁₆N₂O₃
• Molecular Weight: 0
• Mol File: 714-59-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 275.8°C at 760 mmHg
• Flash Point: 104.7°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 0.00498mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: 1,3-dimethylbarbital(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dimethylbarbital(714-59-0)
• EPA Substance Registry System: 1,3-dimethylbarbital(714-59-0)

Safety Data

• Hazardous Substances Data: 714-59-0(Hazardous Substances Data)

Usage

Classification

Barbiturate derivative

Function

Central nervous system depressant

Primary use

Sedative and hypnotic medication for insomnia and other sleep disorders

Mechanism of action

Enhances the activity of gamma-aminobutyric acid (GABA) in the brain

Administration

Typically oral form

Legal status

Schedule IV controlled substance

Potential for abuse

Yes, due to its potential for abuse and dependence

Side effects

Drowsiness, dizziness, impaired coordination

Caution

Should be used with caution, especially in combination with other central nervous system depressants

InChI:InChI=1/C10H16N2O3/c1-5-10(6-2)7(13)11(3)9(15)12(4)8(10)14/h5-6H2,1-4H3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 75-03-6 ethyl iodide 
• 67-56-1 methanol 
• 50-11-3 Gemonil 
• 54856-83-6 3-dimethylamino-2,2-dimethyl-2H-azirine 

Relevant articles and documents

Reactions of 3-(Dimethylamino)-2,2-dimethyl-2H-azirines with Barbituric-Acid Derivatives

The reaction of 3-(dimethylamino)-2,2-dimethyl-2H-azirine (1) and 5,5-disubstituted barbituric acids 5 in i-PrOH at ca. 70 deg gives 2-alkanamides of type 6 in good yields (Scheme 1).The formation of 6 proceeds with loss of CO2; various reaction mechanisms with a zwitterionic 1:1 adduct B as common intermediate are discussed (Schemes 2 and 5).Thermolysis of product 6 leads to 2-alkyl-5-(dimethylamino)-4,4-dimethyl-4H-imidazoles 8 or the tautomeric 2-alkylidene derivatives 8'via elimination of HNCO (Scheme 3).The latter undergoes trimerization to give 1,3,5-triazine-2,4,6-trione.No reaction is observed with 1,5,5-trisubstituted barbiturates and 1 in refluxing i-PrOH, but an N-alkylation of the barbiturate occurs in the presence of morpholine (Scheme 4).This astonishing reaction is explained by a mechanism via formation of the 2-alkoxy-2-(dimethylamino)aziridinium ion H which undergoes ring opening to give the O-alkylated 2-amino-N1,N1-dimethylisobutyramide I as alkylating reagent (Scheme 4).