3,3'-Diindolylmethane

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]

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	1968-05-4 Y
3D model (JSmol)	Interactive image
Beilstein Reference	223072
ChEBI	CHEBI:50182 Y
ChEMBL	ChEMBL446452 Y
ChemSpider	2963 Y
DrugBank	DB11875
ECHA InfoCard	100.124.716
EC Number	606-355-3
IUPHAR/BPS	11208
PubChem CID	3071
UNII	SSZ9HQT61Z Y
CompTox Dashboard (EPA)	DTXSID8037047
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 Y Key: VFTRKSBEFQDZKX-UHFFFAOYSA-N Y 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
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 YN ?) Infobox references

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]

Researchers from Ben-Gurion University of the Negev, in collaboration with teams from Sichuan University and the National University of Singapore, found that DIM (a naturally occurring molecule also referred to as bisindole) can reduce biofilms responsible for dental plaque and cavities by a remarkable 90%. ^[7]

See also

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