10095-06-4

Basic information

• Product Name: mebikar
• Synonyms: mebikar;2,4,6,8-Tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]-3,7-oxandione;3a,4,6,6a-Tetrahydro-1,3,4,6-tetramethylimidazo[4,5-d]imidazole-2,5(1H,3H)-dione;4,5-(1,3-Dimethylureylene)-1,3-dimethylimidazolidine-2-one;Mebicar;1,3,4,6-tetramethyl-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione;1,3,4,6-tetramethyl-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-quinone;1,3,4,6-Tetramethyl-tetrahydro-imidazo[4,5-d]imidazole-2,5-dione
• CAS NO: 10095-06-4
• Molecular Formula: C₈H₁₄N₄O₂
• Molecular Weight: 198.225
• Mol File: 10095-06-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 362.2 °C at 760 mmHg
• Flash Point: 171.9 °C
• Appearance: /
• Density: 1.237 g/cm³
• Vapor Pressure: 1.96E-05mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: mebikar(CAS DataBase Reference)
• NIST Chemistry Reference: mebikar(10095-06-4)
• EPA Substance Registry System: mebikar(10095-06-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 10095-06-4(Hazardous Substances Data)

Usage

General Description

Mebikar, also known as mebicar, is a psychoactive drug that acts as an anxiolytic and mild sedative. It is a derivative of the neurotransmitter GABA and works by increasing the brain's production of GABA, which has a calming effect on the central nervous system. This drug is primarily used to treat anxiety, stress, and emotional instability, and has also been studied for its potential in treating alcohol withdrawal symptoms. Mebikar is known for its low sedative and muscle relaxant effects, making it a favorable option for patients who need anxiety relief without causing significant drowsiness or impairment. Overall, mebikar is considered to be a safe and effective medication for managing anxiety and related conditions.

InChI:InChI=1/C8H14N4O2/c1-9-5-6(11(3)7(9)13)12(4)8(14)10(5)2/h5-6H,1-4H3

Synthetic route

Glyoxal (131543-46-9) + N,N'-Dimethylurea (96-31-1) → mebicar (10095-06-4)

Conditions	Yield
With 1-hydroxyethylene-(1,1-diphosphonic acid) In water at 80℃; for 1h; Green chemistry;	62%
With 1-hydroxyethylene-(1,1-diphosphonic acid) In water at 80℃; for 2h; Green chemistry;	62%

4,6,8-trimethyl-2-trimethylsilyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione + methyl iodide (74-88-4) → mebicar (10095-06-4)

Conditions	Yield
With silver perchlorate at 20℃; for 2h;	53%

Glyoxal (131543-46-9) + 1,1-Dimethylurea (598-94-7) → mebicar (10095-06-4)

Conditions	Yield
With hydrogenchloride; water

1,3,4-trimethyl-tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione (263403-90-3) → mebicar (10095-06-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / (Me3Si)2NH / CH2Cl2 / 1 h / 20 °C 2: 53 percent / AgClO4 / 2 h / 20 °C View Scheme

mebicar (10095-06-4) → 3,7-dihydroxy-2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo<3.3.0>octane-3,7-diylium bis(trifluoromethanesulfonate)

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 70℃; for 1h;	97%

europium(III) nitrate hexahydrate + mebicar (10095-06-4) → [Eu(2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo(3.3.0)octane-3,7-dione)(H2O)2(nitrate)3]2

Conditions	Yield
In acetone Sealed tube;	89%

gadolinium(III) nitrate hexahydrate + mebicar (10095-06-4) → C16H32Gd2N14O24*(x)H2O

Conditions	Yield
In acetone	84%

samarium(III) nitrate hexahydrate + mebicar (10095-06-4) → [Sm(2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo(3.3.0)octane-3,7-dione)(H2O)2(NO3)3]2

Conditions	Yield
In acetone for 0.0833333 - 0.166667h;	83%

mebicar (10095-06-4) → 2,5-dichloro-1,3,4,6-tetramethyl-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-1,4-diylium dichloride

Conditions	Yield
With phosgene In dichloromethane at 50 - 60℃; for 2h;	67%

mebicar (10095-06-4) → bis(7-oxo-2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo<3.3.0>octane-3-ylium) ether bis(trifluoromethanesulfonate) (101074-07-1)

Conditions	Yield
With trifluoromethylsulfonic anhydride In chloroform for 1h; Heating;	59%

mebicar (10095-06-4) + nitric acid (7697-37-2) → 1-nitro-3.4.6-trimethyl-acetylenediurein

mebicar (10095-06-4) → (7-oxo-2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo<3.3.0>octane)-2-(N-methyl-N-phenyliminium) trifluoromethanesulfonate (101074-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / triflic anhydride / CHCl3 / 1 h / Heating 2: 62 percent / acetonitrile / 1 h View Scheme

mebicar (10095-06-4) + nickel(II) nitrate → Ni(2+)*C8H14N4O2*4H2O*2NO3(1-)=[Ni(C8H14N4O2)(H2O)4](NO3)2

Conditions	Yield
In water molar ratio Ni:ligand=1:2, satd. solns.; filtration, crystn. (several d), filtration, washing (H2O), drying (in air); elem. anal.;

mebicar (10095-06-4) + cobalt(II) bromide → Co(C8H14N4O2)2(H2O)2Br2*2H2O

Conditions	Yield
In water molar ratio Co:ligand=1:2, satd. solns.; filtration, crystn. (several d), filtration, washing (H2O), drying (in air); elem. anal.;

mebicar (10095-06-4) + copper(ll) bromide (7789-45-9) → Cu2(C8H14N4O2)3Br4*2H2O

Conditions	Yield
In water molar ratio Cu:ligand=1:4, satd. solns.; filtration, crystn. (several d), filtration, washing (H2O), drying (in air); elem. anal.;

mebicar (10095-06-4) + nickel dibromide → Ni(C8H14N4O2)2(H2O)2Br2 (105082-84-6)

Conditions	Yield
In water molar ratio Ni:ligand=1:2, satd. solns.; filtration, crystn. (several d), filtration, washing (H2O), drying (in air); elem. anal.;

mebicar (10095-06-4) → Ni(2+)*2C8H14N4O2*2Br(1-)=Ni(C8H14N4O2)2Br2

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: neat (no solvent) View Scheme

mebicar (10095-06-4) → Co(2+)*2C8H14N4O2*2Br(1-)=Co(C8H14N4O2)2Br2

Conditions	Yield
Multi-step reaction with 2 steps 1: water 2: neat (no solvent) View Scheme

mebicar (10095-06-4) → 2,2,5,5-tetrafluoro-1,3,4,6-tetramethyloxyhydroimidazo[4,5-d]imidazole

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / dichloromethane / 2 h / 50 - 60 °C 2: Carbonyl fluoride / acetonitrile / 25 °C / Inert atmosphere View Scheme

mebicar (10095-06-4) → N,N'-{1,3,4,6-tetramethyltetrahydroimidazo-[4,5-d]imidazole-2,5(1H,3H)-diylidene}bis(N-ethylethanoaminium)dichloride

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / dichloromethane / 2 h / 50 - 60 °C 2: dichloromethane / 3 h / 20 °C View Scheme

mebicar (10095-06-4) → N,N'-{1,3,4,6-tetramethyltetrahydroimidazo-[4,5-d]imidazole-2,5(1H,3H)-diylidene}bis(N-methylmethanoaminium)dichloride

Conditions	Yield
Multi-step reaction with 2 steps 1: phosgene / dichloromethane / 2 h / 50 - 60 °C 2: dichloromethane / 3 h / 20 °C View Scheme

Upstream product

• 131543-46-9 Glyoxal 
• 96-31-1 N,N'-Dimethylurea 
• 263403-90-3 1,3,4-trimethyl-tetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione 
• 74-88-4 methyl iodide 
• 598-94-7 1,1-Dimethylurea 

Downstream Products

• 101074-20-8 (7-oxo-2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo<3.3.0>octane)-2-(N-methyl-N-phenyliminium) trifluoromethanesulfonate 

Relevant articles and documents

N-silylation of 2,4,6-trialkyl-2,4,6,8-tetraazabicyclo-|3.3.0|octane-3,7-diones

N-Trimethylsilyl derivatives of 2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-diones have been prepared for the first time and the electrophilic substitution reaction of the trimethylsilyl group has been studied.

New Synthesis of 2,4,6,8-Tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione Using Etidronic Acid as a “Green” Catalyst

Abstract: A new method has been developed for the synthesis of2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione in 62% yieldusing etidronic acid [1-hydroxyethane-1,1-diylbis(phosphonic acid), HEDP] as a“green” catalyst. A plausible stepwise mechanism of the reaction has beenproposed and partially confirmed by NMR data and studying model processes. Theeffects of the reaction medium and HEDP on particular species involved in thereaction, namely N,N′-dimethylurea, 4,5-dihydroxy-1,3-dimethylimidazolidin-2-one,and 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione, havebeen studied by 1H and 13CNMR spectroscopy in D2O, neutral and acidified solutions(acetic acid-d4), andsolutions containing 1 equiv of HEDP.