Editing Cannabinoid (section)

{{Short description|Compounds found in cannabis}}
{{use dmy dates|date=May 2023}}
{{Cannabis sidebar}}

'''Cannabinoids''' ({{IPAc-en|k|ə|ˈ|n|æ|b|ə|n|ɔɪ|d|z|,|_|ˈ|k|æ|n|ə|b|ə|n|ɔɪ|d|z}}) are several structural classes of compounds found primarily in the ''[[Cannabis]]'' plant or as synthetic compounds.<ref>{{cite journal | vauthors = Abyadeh M, Gupta V, Paulo JA, Gupta V, Chitranshi N, Godinez A, Saks D, Hasan M, Amirkhani A, McKay M, Salekdeh GH, Haynes PA, Graham SL, Mirzaei M | display-authors = 3 | title = A Proteomic View of Cellular and Molecular Effects of Cannabis | journal = Biomolecules | volume = 11 | issue = 10 | pages = 1411–1428 | date = September 2021 | pmid = 34680044 | pmc = 8533448 | doi = 10.3390/biom11101411 | doi-access = free }}</ref><ref>{{cite web |title=Marijuana, also called: Cannabis, Ganja, Grass, Hash, Pot, Weed |url=https://medlineplus.gov/marijuana.html |website=Medline Plus |date=3 July 2017 |access-date=19 February 2020 |archive-date=20 April 2023 |archive-url=https://web.archive.org/web/20230420163636/https://medlineplus.gov/marijuana.html |url-status=live }}</ref> The most notable cannabinoid is the [[phytocannabinoid]] [[tetrahydrocannabinol]] (THC) (delta-9-THC), the primary psychoactive compound in [[Cannabis (drug)|cannabis]].<ref name="lambert">{{cite journal | vauthors = Lambert DM, Fowler CJ | title = The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 16 | pages = 5059–5087 | date = August 2005 | pmid = 16078824 | doi = 10.1021/jm058183t }}</ref><ref>{{cite book|title=Cannabinoids |url=https://archive.org/details/cannabinoidshand00pert |url-access=limited | veditors = Pertwee R |publisher=Springer-Verlag |year=2005 |isbn=978-3-540-22565-2 |page=[https://archive.org/details/cannabinoidshand00pert/page/n11 2]}}</ref> [[Cannabidiol]] (CBD) is also a major constituent of temperate cannabis plants and a minor constituent in tropical varieties.<ref>{{cite web |url=http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1962-01-01_3_page005.html |title=Bulletin on Narcotics – 1962 Issue 3 – 004 |publisher=UNODC (United Nations Office of Drugs and Crime) |date=1962-01-01 |access-date=2014-01-15 |archive-date=2019-04-02 |archive-url=https://web.archive.org/web/20190402062238/http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1962-01-01_3_page005.html |url-status=live }}</ref> At least 100 distinct phytocannabinoids have been isolated from cannabis, although only four (i.e., THCA, CBDA, CBCA and their common precursor CBGA) have been demonstrated to have a biogenetic origin.<ref name=":0">{{cite journal | vauthors = Aizpurua-Olaizola O, Soydaner U, Öztürk E, Schibano D, Simsir Y, Navarro P, Etxebarria N, Usobiaga A | display-authors = 6 | title = Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes | journal = Journal of Natural Products | volume = 79 | issue = 2 | pages = 324–331 | date = February 2016 | pmid = 26836472 | doi = 10.1021/acs.jnatprod.5b00949 | url = https://figshare.com/articles/journal_contribution/5028338 | access-date = 2022-12-02 | archive-date = 2023-01-05 | archive-url = https://web.archive.org/web/20230105025827/https://figshare.com/articles/journal_contribution/Evolution_of_the_Cannabinoid_and_Terpene_Content_during_the_Growth_of_Cannabis_sativa_Plants_from_Different_Chemotypes/5028338 | url-status = live | url-access = subscription }}</ref> It was reported in 2020 that phytocannabinoids can be found in other plants such as [[rhododendron]], [[licorice]] and [[liverwort]],<ref>{{cite journal | vauthors = Gülck T, Møller BL | title = Phytocannabinoids: Origins and Biosynthesis | journal = Trends in Plant Science | volume = 25 | issue = 10 | pages = 985–1004 | date = October 2020 | pmid = 32646718 | doi = 10.1016/j.tplants.2020.05.005 | s2cid = 220465067 | doi-access = free }}</ref> and earlier in [[Echinacea]].

Phytocannabinoids are multi-ring phenolic compounds structurally related to THC,<ref>Pate, DW (1999). Anandamide structure-activity relationships and mechanisms of action on intraocular pressure in the normotensive rabbit model. Kuopio University Publications A. Pharmaceutical Sciences Dissertation 37, {{ISBN|951-781-575-1}}</ref> but endocannabinoids are fatty acid derivatives. Nonclassical synthetic cannabinoids (cannabimimetics) include [[aminoalkylindole]]s, 1,5-diarylpyrazoles, [[quinoline]]s, and arylsulfonamides as well as [[eicosanoid]]s related to endocannabinoids.<ref name="lambert" />