Thymoquinone

Thymoquinone is a phytochemical compound found in the plant Nigella sativa. It is also found in select cultivated Monarda fistulosa plants grown in the U.S. and steam distilled producing an essential oil.

Thymoquinone
Names
IUPAC name
2-Isopropyl-5-methylbenzo-1,4-quinone
Other names
Thymoquinone
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.020
PubChem CID
Properties
Chemical formula
 C10H12O2
Molar mass 164.204 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

In laboratory experiments in cells and in animals, it has shown antiinflammatory and antioxidant effects, and has been studied in models of cardiovascular diseases and diabetes,[1] neurodegenerative diseases and stroke,[2] and cancer.[3] A 2016 study suggests thymoquinone may have opioid tolerance-reduction effects.[4]

It has been classified as a pan-assay interference compound, which binds indiscriminately to many proteins.[5]

See also
  • Dithymoquinone, a dimer of thymoquinone
  • 2,5-Dimethoxy-p-cymene

References
  1. Farkhondeh T, Samarghandian S, Borji A (September 2017). "An overview on cardioprotective and anti-diabetic effects of thymoquinone". Asian Pacific Journal of Tropical Medicine. 10 (9): 849–854. doi:10.1016/j.apjtm.2017.08.020. PMID 29080612.
  2. Khazdair MR (2015-01-01). "The Protective Effects of Nigella sativa and Its Constituents on Induced Neurotoxicity". Journal of Toxicology. 2015: 841823. doi:10.1155/2015/841823. PMC 4641935. PMID 26604923.
  3. Asaduzzaman Khan M, Tania M, Fu S, Fu J (August 2017). "Thymoquinone, as an anticancer molecule: from basic research to clinical investigation". Oncotarget. 8 (31): 51907–51919. doi:10.18632/oncotarget.17206. PMC 5584300. PMID 28881699.
  4. Hosseinzadeh H, Parvardeh S, Masoudi A, Moghimi M, Mahboobifard F (2016). "Attenuation of morphine tolerance and dependence by thymoquinone in mice". Avicenna Journal of Phytomedicine. 6 (1): 55–66. PMC 4884218. PMID 27247922.
  5. Baell JB (March 2016). "Feeling Nature's PAINS: Natural Products, Natural Product Drugs, and Pan Assay Interference Compounds (PAINS)". Journal of Natural Products. 79 (3): 616–28. doi:10.1021/acs.jnatprod.5b00947. PMID 26900761.
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