CANNABINOL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H26O2
Molecular Weight	310.4299
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC1=CC2=C(C(O)=C1)C3=C(C=CC(C)=C3)C(C)(C)O2

InChI

InChIKey=VBGLYOIFKLUMQG-UHFFFAOYSA-N

InChI=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

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20117100 | https://www.ncbi.nlm.nih.gov/pubmed/28169144 | https://www.ncbi.nlm.nih.gov/pubmed/22543671 | https://www.ncbi.nlm.nih.gov/pubmed/2253656

Cannabinol is a cannabinoid isolated from the plant Cannabis that is a metabolite of tetrahydrocannabinol (THC), with potential immunosuppressive and anti-inflammatory activities. Cannabinol acts as a partial agonist at the CB1 receptors, but it preferentially binds to the cannabinoid G-protein coupled receptor CB2, which is mainly expressed on a variety of immune cells, such as T-cells, B-cells, macrophages and dendritic cells. Stimulation of CB2 receptors by cannabinol may both trigger apoptosis in these cells and inhibit the production of a variety of cytokines. In the United States, federal and state laws regarding the legality of cannabis products are confusing and at times contradictory. CBN is not listed in the list of scheduled controlled substances in the USA.

Approval Year

PubMed

Title	Date	PubMed
Cannabinol enhancement of interleukin-2 (IL-2) expression by T cells is associated with an increase in IL-2 distal nuclear factor of activated T cell activity.	2002 Feb	11809870
The cannabinoid dexanabinol is an inhibitor of the nuclear factor-kappa B (NF-kappa B).	2004 Sep	15380375
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.	2008 Jun 11	18550765
Cannabinoids Delta(9)-tetrahydrocannabinol and cannabidiol differentially inhibit the lipopolysaccharide-activated NF-kappaB and interferon-beta/STAT proinflammatory pathways in BV-2 microglial cells.	2010 Jan 15	19910459

Patents

Name

Type

Language

CANNABINOL

Official Name

English

cannabinol [INN]

Common Name

English

3-AMYL-1-HYDROXY-6,6,9-TRIMETHYL-6H-DIBENZO(B,D)PYRAN

Systematic Name

English

NSC-134455

Code

English

CBN

Common Name

English

CANNABINOL [MI]

Common Name

English

6,6,9-TRIMETHYL-3-PENTYL-6H-DIBENZO(B,D)PYRAN-1-OL

Systematic Name

English

6H-DIBENZO(B,D)PYRAN-1-OL, 6,6,9-TRIMETHYL-3-PENTYL-

Systematic Name

English

Cannabinol [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C574