3,3'-Diindolylmethane

3,3'-Diindolylmethane
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
CAS Number
3D model (JSmol)
Beilstein Reference
 223072
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.124.716
EC Number
  • 606-355-3
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2 checkY
    Key: VFTRKSBEFQDZKX-UHFFFAOYSA-N checkY
  • InChI=1/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
  • InChI=1/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
    Key: VFTRKSBEFQDZKX-UHFFFAOYAU
SMILES
  • c4ccc3c(Cc1c[nH]c2ccccc12)c[nH]c3c4
Properties
Chemical formula
 C17H14N2
Molar mass 246.313 g·mol−1
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation mark
Signal word
 Warning
Hazard statements
 H315, H319, H335, H413
Precautionary statements
 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).
☒N verify (what is checkY☒N ?)
Infobox references

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]

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, no clinical trials have been conducted that confirm the effectiveness of DIM in reducing plaque.

See also

  • Glucobrassicin, precursor to indole-3-carbinol
  • Phytochemicals

References

  1. ^ a b c d "Indole-3-carbinol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 July 2017. Retrieved 11 July 2022.
  2. ^ "3,3'-Diindolylmethane". PubChem, US National Library of Medicine. 9 July 2022. Retrieved 11 July 2022.
  3. ^ Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clinical Epigenetics. 3 (1): 4. doi:10.1186/1868-7083-3-4. PMC 3255482. PMID 22247744.
  4. ^ "DIM".
  5. ^ Andhika B. Mahardhika; et al. (March 2023). "Design, synthesis, and structure–activity relationships of diindolylmethane derivatives as cannabinoid CB2 receptor agonists". Archiv der Pharmazie. 356 (3): e2200493. doi:10.1002/ardp.202200493. PMID 36437108.{{cite journal}}: CS1 maint: article number as page number (link)
  6. ^ Paolo Tucci; et al. (2023). "The Plant Derived 3-3′-Diindolylmethane (DIM) Behaves as CB2 Receptor Agonist in Prostate Cancer Cellular Models". International Journal of Molecular Sciences. 24 (4): 3620. doi:10.3390/ijms24043620. hdl:2164/20232. PMC 9962283. PMID 36835033.
  7. ^ Yifat Baruch; et al. (6 June 2023). "3,3′-Diindolylmethane (DIM): A Potential Therapeutic Agent against Cariogenic Streptococcus mutans Biofilm". Antibiotics. 12 (6): 1017. doi:10.3390/antibiotics12061017. PMC 10295630. PMID 37370336.
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