3,3'-Diindolylmethane

3,3'-Diindolylmethane
IUPAC name 3,3′-methanediylbis(1H-indole)
Other names 3-(1H-Indol-3-ylmethyl)-1H-indole 3,3'-Methylenebis-1H-indole DIM
Identifiers
CAS number	1968-05-4
PubChem	3071
ChemSpider	2963 Y
ChEBI	CHEBI:50182
ChEMBL	CHEMBL446452 Y
Jmol-3D images	Image 1 Image 2
SMILES C1=CC=C2C(=C1)C(=CN2)CC3=CNC4=CC=CC=C43 c1cccc2c1c(cn2)Cc4c3ccccc3nc4
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
Properties
Molecular formula	C17H14N2
Molar mass	246.31 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

3,3′-Diindolylmethane or 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] The reputation of Brassica vegetables as healthy foods rests in part on the activities of diindolylmethane.^[2][3]

Properties

DIM has the biological properties listed in the chart below. Because of its various potent anticancer properties, the National Cancer Institute of the United States has begun clinical trials of DIM as a therapeutic for numerous forms of cancer.^{[4] [5]}

Biological activities of 3,3'-diindolylmethane

Uses

At the present time, DIM is used to treat recurring respiratory papillomatosis, a rare respiratory disease with tumors in the upper respiratory tracts caused by the human papilloma virus.^{[citation needed]} In addition, DIM is in Phase III clinical trials for cervical dysplasia, a precancerous condition also caused by the human papilloma virus.^{[citation needed]} Similarly, it has been studied and shown promising results as a immunostimulant against HPV.

See also

• Phytochemicals

References

1. ^ Rakel D.. Integrative Medicine. 
2. ^ Gong Y. Sohn H. Xue L. Firestone GL. Bjeldanes LF (2006). "3,3'-Diindolylmethane is a novel mitochondrial H(+)-ATP synthase inhibitor that can induce p21(Cip1/Waf1) expression by induction of oxidative stress in human breast cancer cells". Cancer Research 66 (9): 4880–4887. doi:10.1158/0008-5472.CAN-05-4162. PMID 16651444. 
3. ^ Acharya A. Das I. Singh S. Saha T. (2010). "Chemopreventive properties of indole-3-carbinol, diindolylmethane and other constituents of cardamom against carcinogenesis". Recent patents on food, nutrition & agriculture 2 (2): 166–177. doi:10.2174/1876142911002020166. 
4. ^ Rogan EG (2006). "The natural chemopreventive compound indole-3-carbinol: state of the science". In Vivo 20 (2): 221–228. PMID 16634522. 
5. ^ Kim YS. Milner JA (2005). "Targets for indole-3-carbinol in cancer prevention". Journal of Nutritional Biochemistry 16 (2): 65–73. doi:10.1016/j.jnutbio.2004.10.007. PMID 15681163. 

External links

• Diindolylmethane Information Resource Center