5,6-DIMETHYLBENZIMIDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10N2
Molecular Weight	146.1891
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C)C=C2N=CNC2=C1

InChI

InChIKey=LJUQGASMPRMWIW-UHFFFAOYSA-N

InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11)

HIDE SMILES / InChI

Molecular Formula	C9H10N2
Molecular Weight	146.1891
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Genetic disorders of vitamin B₁₂ metabolism: eight complementation groups--eight genes.	2010-11-29	21114891
Redetermination of the X-ray structure of nitroxylcobalamin: base-on nitroxylcobalamin exhibits a remarkably long Co-N(dimethylbenzimidazole) bond distance.	2010-11-28	20890534
Sirtuin chemical mechanisms.	2010-08	20132909
Toxicology and drug delivery by cucurbit[n]uril type molecular containers.	2010-05-06	20463906
Thermolability of mutant MMACHC protein in the vitamin B12-responsive cblC disorder.	2010-05	20219402
(E)-1,2-Bis(1-propyl-5,6-dimethyl-1H-benzimidazol-2-yl)ethene.	2010-02-10	21580350
Purification and some properties of wild-type and N-terminal-truncated ethanolamine ammonia-lyase of Escherichia coli.	2010-01	19762342
The cobinamide amidohydrolase (cobyric acid-forming) CbiZ enzyme: a critical activity of the cobamide remodelling system of Rhodobacter sphaeroides.	2009-12	19889098
Structure-based mechanism of ADP-ribosylation by sirtuins.	2009-11-27	19801667
Apparent ruminal synthesis and intestinal disappearance of vitamin B12 and its analogs in dairy cows.	2009-09	19700714
(N-n-Butyl-pyridine-4-carbothio-amide-κN)chloridobis(dimethyl-glyoximato-κN,N')cobalt(III) hemihydrate.	2009-06-20	21582722
Stabilization of the base-off forms of vitamin B(12) and coenzyme B(12) by encapsulation of the alpha-axial 5,6-dimethylbenzimidazole ligand with cucurbit[7]uril.	2009-05-14	19381421
Residue Phe112 of the human-type corrinoid adenosyltransferase (PduO) enzyme of Lactobacillus reuteri is critical to the formation of the four-coordinate Co(II) corrinoid substrate and to the activity of the enzyme.	2009-04-14	19236001
[Effect of a corrinoid on Methanosarcina barkeri DNA synthesis].	2009-04-02	19334592
Ag4L2 nanocage as a building unit toward the construction of silver metal strings.	2008-11-17	18847253
Identification of metabolites with anticancer properties by computational metabolomics.	2008-06-17	18559081
Metabolism of halophilic archaea.	2008-03	18278431
Medical implications of benzimidazole derivatives as drugs designed for targeting DNA and DNA associated processes.	2008	18691037
Analysis of vibrational spectra of 5,6-dimethyl benzimidazole based on density functional theory calculations.	2007-11	17475545
Pseudovitamin B(12) is the corrinoid produced by Lactobacillus reuteri CRL1098 under anaerobic conditions.	2007-10-16	17888910
X-ray structural characterization of imidazolylcobalamin and histidinylcobalamin: cobalamin models for aquacobalamin bound to the B12 transporter protein transcobalamin.	2007-04-30	17407285
BluB cannibalizes flavin to form the lower ligand of vitamin B12.	2007-03-22	17377583
Biochemistry: molecular cannibalism.	2007-03-22	17377573
The enzymatic activation of coenzyme B12.	2006-03-07	16482346
Differentiation of ionised benzimidazole from its isomeric alpha-distonic ion by collision-induced dissociation and neutralisation-reionisation mass spectrometry.	2005	16204804
Solution structure and thermolysis of Cobeta-5'-deoxyadenosylimidazolylcobamide, a coenzyme B12 analogue with an imidazole axial nucleoside.	2004-12-13	15578853
Spectroscopic and computational studies on the adenosylcobalamin-dependent methylmalonyl-CoA mutase: evaluation of enzymatic contributions to Co-C bond activation in the Co3+ ground state.	2004-07-07	15225058
Cobalamin-dependent methionine synthase: probing the role of the axial base in catalysis of methyl transfer between methyltetrahydrofolate and exogenous cob(I)alamin or cob(I)inamide.	2003-12-16	14661978
Reactions of nitric oxide with vitamin B12 and its precursor, cobinamide.	2003-07-29	12873151
Formation of the dimethylbenzimidazole ligand of coenzyme B(12) under physiological conditions by a facile oxidative cascade.	2003-06-26	12816411
Spectroscopic and computational studies of Co3+-corrinoids: spectral and electronic properties of the B12 cofactors and biologically relevant precursors.	2003-05-14	12733931
Alpha-5,6-dimethylbenzimidazole adenine dinucleotide (alpha-DAD), a putative new intermediate of coenzyme B12 biosynthesis in Salmonella typhimurium.	2003-04	12686640
The crystal structure of coenzyme B12-dependent glycerol dehydratase in complex with cobalamin and propane-1,2-diol.	2002-09	12230560
Synthesis of adenosylcobinamide 2-chlorophenyl phosphate, a zwitterionic cobinamide phosphate analog of adenosylcobalamin en route to crystallizable cobinamides.	2002-08-15	12161307
Enzymatic activity of coenzyme B(12) derivatives with altered axial nucleotides: probing the mechanochemical triggering hypothesis in ribonucleotide reductase.	2001-11-05	11681909
Equilibrium and kinetic studies on the reactions of alkylcobalamins with cyanide.	2001-10-08	11578192
Structural investigation of the biosynthesis of alternative lower ligands for cobamides by nicotinate mononucleotide: 5,6-dimethylbenzimidazole phosphoribosyltransferase from Salmonella enterica.	2001-10-05	11441022
Renal interstitial cGMP mediates natriuresis by direct tubule mechanism.	2001-09	11566896
Assessment of the existence of hyper-long axial Co(II)-N bonds in cobinamide B(12) models by using electron paramagnetic resonance spectroscopy.	2001-04-11	11457072
Thermodynamic and kinetic studies on the reaction between the vitamin B12 derivative beta-(N-methylimidazolyl)cobalamin and N-methylimidazole: ligand displacement at the alpha axial site of cobalamins.	2001-03-26	11261947
Molecular modeling of the mechanochemical triggering mechanism for catalysis of carbon-cobalt bond homolysis in coenzyme B12.	2001-01-15	11237251

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:31:47 GMT 2025` Edited by `admin` on `Mon Mar 31 19:31:47 GMT 2025`
Record UNII	553XI1DS20
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

5,6-DIMETHYLBENZIMIDAZOLE

Systematic Name

English

NSC-68316

Preferred Name

English

5,6-DIMETHYL-1H-BENZIMIDAZOLE

Systematic Name

English

BENZIMIDAZOLE, 5,6-DIMETHYL-

Systematic Name

English

1H-BENZIMIDAZOLE, 5,6-DIMETHYL-

Systematic Name

English

5,6-DIMETHYLBENZIMIDAZOLE [MI]

Common Name

English

Code System Code Type Description

CAS

582-60-5