|Jmol-3D images||Image 1
|Molar mass||246.31 g mol−1|
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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. The reputation of Brassica vegetables as healthy foods rests in part on the activities of diindolylmethane.
DIM has the biological properties listed in the chart below. Because of its various potential anticancer properties, the National Cancer Institute of the United States has begun clinical trials of DIM as a therapeutic for numerous forms of cancer. 
At the present time, DIM is used to treat recurrent respiratory papillomatosis (RRP), a rare respiratory disease with tumors in the upper respiratory tracts caused by the human papilloma virus. In a preliminary study on 64 women, it was well tolerated at the studied dose (2 mg/kg/day), showing some promising results as an immunostimulant against human papilloma virus infection of the cervix, but not at a statistically significant level. In a subsequent double-blind, randomized, placebo-controlled study on 600 women, DIM in vivo had no effect on cytology regarding cervical dysplasia, a precancerous condition also caused by the human papilloma virus.
Recent research suggests possible use as radioprotector and mitigator. DIM (3,3′-diindolylmethane) is a small molecule compound under investigation as a cancer preventive agent. Research shows a potential usage of DIM as a medical countermeasure to prevent or mitigate acute radiation syndrome due to whole body exposure. In this regard, DIM can be administered safely to humans and animals by oral or subcutaneous routes. DIM may also be useful in preventing or mitigating late normal tissue damage due to partial body radiation exposure during cancer treatment. DIM works, in part, by a mechanism distinct from other radioprotectors and mitigators involving stimulation of the DNA damage response, including DNA repair, and activation of cell survival signaling through the transcription factor NF-κB.
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- 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.
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- Del Priore, G.; Gudipudi, D. K.; Montemarano, N.; Restivo, A. M.; Malanowska-Stega, J.; Arslan, A. A. (2010). "Oral diindolylmethane (DIM): Pilot evaluation of a nonsurgical treatment for cervical dysplasia". Gynecologic Oncology 116 (3): 464–467. doi:10.1016/j.ygyno.2009.10.060. PMID 19939441.
- Castañon, A.; Tristram, A.; Mesher, D.; Powell, N.; Beer, H.; Ashman, S.; Rieck, G.; Fielder, H.; Fiander, A.; Sasieni, P. (2011). "Effect of diindolylmethane supplementation on low-grade cervical cytological abnormalities: Double-blind, randomised, controlled trial". British Journal of Cancer 106 (1): 45–52. doi:10.1038/bjc.2011.496. PMC 3251847. PMID 22075942.
- Saijun Fan, Qinghui Meng, Jiaying Xu, Yang Jiao, Lin Zhao, Xiaodong Zhang, Fazlul H. Sarkar, Milton L. Brown, Anatoly Dritschilo, and Eliot M. Rosen "DIM (3,3'-diindolylmethane) confers protection against ionizing radiation by a unique mechanism" PNAS 2013 : 1308206110v1-201308206.