5,6-Dimethylbenzimidazole

5,6-Dimethylbenzimidazole

Names
Preferred IUPAC name 5,6-Dimethyl-1H-1,3-benzimidazole
Identifiers
CAS Number	582-60-5 Y
3D model (JSmol)	Interactive image
Beilstein Reference	116595
ChEBI	CHEBI:15890
ChEMBL	ChEMBL351132
ChemSpider	655
DrugBank	DB02591
ECHA InfoCard	100.008.627
EC Number	209-488-1
Gmelin Reference	279255
KEGG	C03114
PubChem CID	675
UNII	553XI1DS20
CompTox Dashboard (EPA)	DTXSID70870631
InChI InChI=1S/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11) Key: LJUQGASMPRMWIW-UHFFFAOYSA-N InChI=1/C9H10N2/c1-6-3-8-9(4-7(6)2)11-5-10-8/h3-5H,1-2H3,(H,10,11) Key: LJUQGASMPRMWIW-UHFFFAOYAV
SMILES CC1=CC2=C(C=C1C)N=CN2
Properties
Chemical formula	C9H10N2
Molar mass	146.193 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335, H412
Precautionary statements	P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5,6-Dimethylbenzimidazole (DMB) is a naturally occurring derivative of benzimidazole with two methyl groups as substituents on the benzene ring.

5,6-Dimethylbenzimidazole is biosynthesized from flavin mononucleotide by the enzyme 5,6-dimethylbenzimidazole synthase.

Occurrence and uses

Biological significance

5,6-Dimethylbenzimidazole is a substructure of true vitamin B₁₂, where it serves as one of the ligands for the cobalt atom. In part of one of the pathways for cobalamin biosynthesis, DMB is a substrate for nicotinate-nucleotide—dimethylbenzimidazole phosphoribosyltransferase. One form of pseudovitamin B₁₂, i.e. a compound usable by B₁₂-dependent lactic acid bacteria but not by humans, has this group replaced with adenyl. Despite production of pseudo B₁₂ in groups as distantly related as lactic acid bacteria and Cyanobacteria, DMB is preferred over adenine by the vast majority of versions of CobT, the enzyme responsible for making the active phosphoribosylated "lower group" of cobalamin.

Medicinal chemistry

Researchers have explored the pharmacological properties of benzimidazole derivatives, with some displaying antimicrobial, antiviral, anticancer, and antifungal activities. The specific medicinal properties of 5,6-dimethylbenzimidazole may vary based on its structural features and substituents.