3,3'-Diindolylmethane
Chemical compound
From Wikipedia, the free encyclopedia
3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables, such as broccoli, Brussels sprouts, cabbage and kale.[1] It and its parent compound – indole-3-carbinol – are under laboratory research to determine their possible biological properties, particularly in anti-cancer mechanisms.[1][2] DIM is sold as a dietary supplement.[1]
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| Names | |
|---|---|
| Preferred IUPAC name
3,3′-Methylenedi(1H-indole) | |
| Other names
3-(1H-Indol-3-ylmethyl)-1H-indole 3,3′-Methylenebis-1H-indole DIM | |
| Identifiers | |
3D model (JSmol) |
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| 223072 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.124.716 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C17H14N2 | |
| Molar mass | 246.313 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335, H413 | |
| P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, 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).
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Properties
In vitro, DIM has action as a histone deacetylase inhibitor,[1] specifically against HDAC1, HDAC2, and HDAC3.[3] DIM is a metabolite of indole-3-carbinol. [4]
DIM was found to be a mild cannabinoid agonist with low binding affinity for both CB1 and CB2.[5][6]
A study conducted in 2023 by researchers from Ben-Gurion University of the Negev, in collaboration with teams from Sichuan University and the National University of Singapore, found that DIM can reduce biofilms responsible for dental plaque and cavities by 90%.[7] As of 2025[update], no clinical trials have been conducted that confirm the effectiveness of DIM in reducing plaque.
See also
- Glucobrassicin, precursor to indole-3-carbinol
- Phytochemicals