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=CC(O)=C2C(OC(C)(C)C3=CC=C(C)C=C23)=C1

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

HIDE SMILES / InChI

Molecular Formula	C21H26O2
Molecular Weight	310.4299
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Cannabinoids Delta(9)-tetrahydrocannabinol and cannabidiol differentially inhibit the lipopolysaccharide-activated NF-kappaB and interferon-beta/STAT proinflammatory pathways in BV-2 microglial cells.	2010-01-15	19910459
TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons.	2008-06-11	18550765
The cannabinoid dexanabinol is an inhibitor of the nuclear factor-kappa B (NF-kappa B).	2004-09	15380375
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.	2002-02	11809870
Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands.	1996-09	8819477
Cannabinoid inhibition of adenylate cyclase-mediated signal transduction and interleukin 2 (IL-2) expression in the murine T-cell line, EL4.IL-2.	1996-05-31	8662742
Comparison of the pharmacology and signal transduction of the human cannabinoid CB1 and CB2 receptors.	1995-09	7565624
Molecular characterization of a peripheral receptor for cannabinoids.	1993-09-02	7689702
Metabolism of cannabis. IX. Cannabinol: structure of a major metabolite formed in rat liver.	1971-02-08	5575428

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:07 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:07 GMT 2025`
Record UNII	7UYP6MC9GH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-134455

Preferred Name

English

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

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