Compound: Mebicar
SMILES: O=C1N(C2N(C(=O)N(C2N1C)C)C)C
InChIKey: XIUUSFJTJXFNGH-UHFFFAOYSA-N
Synonyms: Mebicar, 10095-06-4, mebikar, Tetramethylglycoluril, Tetrahydro-1,3,4,6-tetramethylimidazo(4,5-d)imidazole-2,5(1H,3H)-dione, 55FE6NPG89, Glycoluril, 1,3,4,6-tetramethyl-, imidazo[4,5-d]imidazole-2,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetramethyl-, DTXSID60143588, 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo-(3.3.0)-octan-3,7-dione, Imidazo(4,5-d)imidazole-2,5(1H,3H)-dione, tetrahydro-1,3,4,6-tetramethyl-, RefChem:810813, DTXCID1066079, (3as,6as)-1,3,4,6-tetramethyl-octahydro-(1,3)diazolo(4,5-d)imidazole-2,5-dione, Temgicoluril, 1,3,4,6-Tetramethyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, Adaptol, 1,3,4,6-tetramethyl-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione, MFCD00184215, 1,3,4,6-Tetramethyltetrahydroimidazo[4,5-d]-imidazole-2,5(1H,3H)-dione, 1,3,4,6-tetramethyl-octahydro-[1,3]diazolo[4,5-d]imidazole-2,5-dione, 1,3,4,6-tetramethyl-1,3,4,6,3a,6a-hexahydro-1,3,4,6-tetraazapentalene-2,5-dion e, 106780-29-4, UNII-55FE6NPG89, Temgicoluril?, 2,4,6,8-Tetramethyl-2,4,6,8-tetraazobizykl(3,3,0)oktandion-3,7 [German], Temgicoluril [WHO-DD], 2,4,6,8-Tetramethyl-2,4,6,8-tetraazobicyclo(3.3.0)octane-3,7-dione, ChemDiv1_025094, TEMGICOLURIL [INN], 2,4,6,8-Tetraazabicyclo[3.3.0]octane-3,7-dione, 2,4,6,8-tetramethyl-, orb1298102, SCHEMBL1465373, CHEMBL3707390, SCHEMBL15685069, HMS658E14, XIUUSFJTJXFNGH-UHFFFAOYSA-, CHEBI:136038, XIUUSFJTJXFNGH-UHFFFAOYSA-N, DTXSID101363121, ALBB-014894, 2,4,6,8-Tetramethyl-2,4,6,8-tetraazobizykl(3,3,0)oktandion-3,7, STK022918, AKOS000487401, DB13522, FT03757, LS-04732, ST027877, DB-234028, HY-139584, CS-0213579, NS00067026, D10508, G12457, F370249, Q4286560, BRD-K76606751-001-01-7, 1,3,4,6-Tetramethyl octahydroimidazo[4,5-d]imidazolidine-2,5-dione, 1,3,4,6-Tetramethyl-3A,6A-dihydroimidazo[4,5-D]imidazole-2 ,5-quinone, 1,3,4,6-Tetramethyltetrahydroimidazo[4,5-d]imidazole-2,5(1H,3H)-dione #, 2,4,6,8-tetramethyl-2,4,6,8-tetraazabicyclo[3.3.0]octane-3,7-dione, Tetrahydro-1,3,4,6-tetramethylimidazo(4,5-D)imidazole-2,5(1H ,3H)-dione, cis-Tetrahydro-1,3,4,6-tetramethylimidazo[4,5-d]imidazole-2,5(1H,3H)-dione, IMIDAZO(4,5-D)IMIDAZOLE-2,5(1H,3H)-DIONE, TETRAHYDRO-1,3,4,6-TETRAMETHYL-, CIS-, Imidazo[4,5-d]imidazole-2,5-(1H,3H)dione, tetrahydro-1,3,4,6-tetramethyl-, InChI=1/C8H14N4O2/c1-9-5-6(11(3)7(9)13)12(4)8(14)10(5)2/h5-6H,1-4H3
Theoretical properties:
molecular_formula: C8H14N4O2
molecular_weight: 198.22 g/mol
exact_mass: 198.11167570 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 47.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Mebicar is an imidazolidinone.
chembl: MEBICAR is a small molecule listed in the ChEMBL database and has reached clinical trial phase -1.0.
wikipedia: Temgicoluril (INNTooltip International Nonproprietary Name), also known as tetramethylglycoluril and sold under the brand names Adaptol and Mebicar, is an anxiolytic medication produced by Latvian pharmaceutical company Olainfarm and sold in Latvia and Russia.
The chemical structure of temgicoluril is somewhat similar to uric acid and it doesn't interact with acids, alkali, oxidants and reducing agents. It seems to affect all major neurotransmitter systems.
Temgicoluril has an effect on the structure of limbic–reticular activity, particularly on hypothalamus emotional zone, as well as on all several basic neuromediator systems – γ aminobutyric acid (GABA), choline, serotonin, and adrenergic activity. It decreases brain norepinephrine levels and increases brain serotonin levels without modulating dopaminergic systems or cholinergic systems.
Temgicoluril purportedly has anti-anxiety (anxiolytic) properties. It is also used to aid smoking cessation. In addition, temgicoluril may be useful in the treatment of ADHD symptoms. In contrast with typical anxiolytic medications such as benzodiazepines, temgicoluril is non-habit forming, non-sedating, and does not impair motor function.
It can be prepared by condensation of 1,3-dimethylurea with glyoxal. One publication described such a procedure. They combined dimethylurea and glyoxal with a catalytic amount of phosphoric acid anhydride in an aqueous solution at room temperature and after sufficient time temgicoluril was conveniently isolated by filtration. The filtrate can be re-used by adding more dimethylurea and glyoxal (no additional catalyst is needed) and obtaining respectable yields, although this requires a longer reaction time.
As of 2021, temgicoluril has not been evaluated outside of Latvia and Russia.