Cannabinol
[6] While some phytocannabinoids have been shown to interact with nociceptive and immune-related signaling via transient receptor potential channels (e.g., TRPV1 and TRPM8), there is currently limited evidence to suggest that CBN acts in this way.This concept describes a widely reported but poorly-understood synergistic effect of certain cannabinoids when phytocannabinoids are coadministered with other naturally-occurring chemical compounds in the cannabis plant (e.g., flavonoids, terpenoids, alkaloids).Exogenous (plant-derived) phytocannabinoids are identified with an asterisk while remaining chemicals represent well-known endocannabinoids (i.e., endogenously produced cannabinoid receptor ligands).In the brain, the canonical mechanism of CB1 receptor activation is a form of short-term synaptic plasticity initiated via retrograde signaling of endogenous CB1 agonists such as 2AG or AEA (two primary endocannabinoids).In contrast, endogenously produced cannabinoids (i.e., endocannabinoids), which also exert effects through CB agonism, are considered eicosanoids, distinguished by notable differences in chemical structure.According to the 2018 Farm Bill,[25] extracts from the Cannabis sativa L. plant, including CBN, are legal under US federal law as long as they have a delta-9 Tetrahydrocannabinol (THC) concentration of 0.3% or less.Although reports are limited, CBN-A has also been measured at very low levels in the cannabis plant, thought to have formed via hydrolyzation of THC-A (see Phytocannabinoid Biosynthesis diagram, below).
cannabidiolcannabinodiolLegal statusIUPAC nameCAS NumberIUPHAR/BPSChemSpiderChEMBLCompTox DashboardECHA InfoCardFormulaMolar massMelting pointSolubility in waterethanolSMILESpsychoactivephytocannabinoidaffinitypartial agonistCB2 receptorsendocannabinoid systemmechanism of actionphytocannabinoidsDelta-9-tetrahydrocannabinolagonistCB1 receptorsreceptorsperipheral nervous systemimmune functionmacrophagesT cellsB cellscytokinesapoptosisANKTM1nociceptivetransient receptor potential channelsanandamideflavonoidsterpenoidsalkaloidsendocannabinoidsligandssynaptic plasticityretrograde signalingendogenouspresynaptic neuronGABAergic interneuronglutamatergic neurondopaminedynorphinoxytocinvasopressinfirst-pass metabolism11-OH-CBNantagonist11-OH-THCbioavailabilityoral administrationCYP450isoformscatalyzedUDP-glucuronosyltransferasesglucuronidationinhalationintravenous administrationCYP2C9CYP3A4Cannabis Sativa Leicosanoidsdouble bond isomersstereoisomersHU-345cannabisEasterfieldcannabis extractin vivoUnited NationsSingle Convention on Narcotic DrugsConvention on Psychotropic Substancestrace amountstetrahydrocannabinolPubChemBibcodeCannabinoidscomparisonCBD-C1Delta-8-THCDelta-9-THCDelta-10-THC7,8-Dihydrocannabinol8,9-DihydrocannabidiolCannabicitranCaryophylleneAlkylamidesEpigallocatechin gallateGallocatecholHexahydrocannabinolPerrottetineneSerinolamide AYangonin3'-OH-THC7-OH-CBD8,11-DiOH-THC11-COOH-THC11-OH-HHC11-OH-Δ8-THC11-OH-Δ9-THCArachidonoyl ethanolamide (AEA; anandamide)2-Arachidonoylglycerol (2-AG)2-Arachidonyl glyceryl ether (2-AGE; noladin ether)2-Oleoylglycerol (2-OG)N-Arachidonoyl dopamine (NADA)N-Arachidonylglycine (NAGly)N-Arachidonoyl serotonin (AA-5-HT)Docosatetraenoylethanolamide (DEA)Lysophosphatidylinositol (LPI)OleamideOleoylethanolamide (OEA)Palmitoylethanolamide (PEA)RVD-HpαStearoylethanolamide (SEA)O-Arachidonoyl ethanolamine (O-AEA; virodhamine)Syntheticcannabinoidreceptoragonists /neocannabinoids1,2-Didehydro-3-oxo-THCO