Editing Cannabinol (section)

{{Short description|Naturally-occurring cannabinoid}}
{{Distinguish|cannabidiol|cannabinodiol}}
{{Use mdy dates|date=October 2022}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477165540
| image = Cannabinol.svg
| image_class = skin-invert-image
| width = 
| image2 = Cannabinol 3D.png
| image_class2 = bg-transparent
| width2 = 

<!-- Clinical data -->
| tradename =
| pregnancy_category =
| legal_CA = Unscheduled
| legal_UK = Class B
| legal_US = Unscheduled
| excretion = 

<!-- Identifiers -->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 521-35-7
| PubChem = 2543
| IUPHAR_ligand = 740
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2447
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7UYP6MC9GH
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C07580
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 74415

<!-- Chemical data -->
| IUPAC_name = 6,6,9-Trimethyl-3-pentyl-benzo[''c'']chromen-1-ol
| C=21 | H=26 | O=2
| SMILES = Oc2cc(cc1OC(c3c(c12)cc(cc3)C)(C)C)CCCCC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C21H26O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h9-13,22H,5-8H2,1-4H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VBGLYOIFKLUMQG-UHFFFAOYSA-N

<!-- Physical data -->
| melting_point = {{convert|169–171|°F|°C|disp=number}}
| melting_notes = <ref>{{PubChem|2543|Cannabinol}}</ref>
| solubility = Insoluble in water,<ref name="CRC">{{cite book | vauthors = Lide DR |title=CRC Handbook of Chemistry and Physics |publisher=CRC Press |year=2012 |isbn=978-1-43988049-4 |pages=3–90 |url=https://books.google.com/books?id=-BzP7Rkl7WkC&pg=PA3-90}}</ref> soluble in methanol<ref name="Sigma">{{cite web | url = https://www.sigmaaldrich.com/SE/en/product/cerillian/c046 | title = Cannabinol solution, analytical standard, for drug analysis | work = Sigma-Aldrich | id = c046 }}</ref> and [[ethanol]]<ref>{{cite web | work = Biotrend | url = http://www.biotrend.com/spec/BN0125.pdf | title = Cannabinol | archive-url = https://web.archive.org/web/20160522054151/http://www.biotrend.com/spec/BN0125.pdf | archive-date=2016-05-22 }}</ref>
}}

'''Cannabinol''' ('''CBN''') is a mildly [[Psychoactive drug|psychoactive]] [[cannabinoid|phytocannabinoid]] that acts as a low [[affinity (chemistry)|affinity]] [[partial agonist]] at both [[CB1 receptor|CB<sub>1</sub>]] and [[CB2 receptor|CB<sub>2</sub> receptor]]s. This activity at CB<sub>1</sub> and CB<sub>2</sub> receptors constitutes interaction of CBN with the [[endocannabinoid system]] (ECS).

Although CBN shares the same [[mechanism of action]] as other [[phytocannabinoids]] (e.g., [[Delta-9-tetrahydrocannabinol]], Δ<sup>9</sup>-THC), it has a lower [[affinity (pharmacology)|affinity]] for CB<sub>1</sub> receptors, meaning that much higher doses of CBN are required in order to experience effects, such as mild sedation.

It was the first cannabinoid to be isolated from cannabis and was discovered in 1896.