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C6888

Supelco

Cannabinol

analytical standard

Synonym(s):

CBN

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About This Item

Empirical Formula (Hill Notation):
C21H26O2
CAS Number:
521-35-7
Molecular Weight:
310.43
MDL number:
MFCD00056774
UNSPSC Code:
41116107
PubChem Substance ID:
329775137
NACRES:
NA.24

grade

analytical standard

Quality Level

100

drug control

USDEA Schedule I; Home Office Schedule 1; regulated under CDSA - not available from Sigma-Aldrich Canada

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)
veterinary

format

neat

storage temp.

2-8°C

SMILES string

CCCCCc1cc(O)c-2c(OC(C)(C)c3ccc(C)cc-23)c1

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

InChI key

VBGLYOIFKLUMQG-UHFFFAOYSA-N

Gene Information

human ... CNR2(1269)
rat ... Cnr1(25248)

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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

Major metabolite of tetrahydrocannabinol that is not psychoactive, CB2 cannabinoid receptor agonist with immunosuppressive properties.

Other Notes

Component of marijuana from C. sativa

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361d

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
056K1384
127H4158
096H4057
077H4115
066H4003

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S J MacLennan et al.
British journal of pharmacology, 124(4), 619-622 (1998-08-05)
The cannabinoid receptor antagonist SR141716A has been suggested to be an inverse agonist at CB1 receptors in some isolated intact tissues. We found that the basal incorporation of [35S]-GTPgammaS in Chinese hamster ovary cells expressing human recombinant CB1 and CB2
A C Herring et al.
Biochemical pharmacology, 55(7), 1013-1023 (1998-05-30)
Immune suppression by cannabinoids has been widely demonstrated in a variety of experimental models. The identification of two major types of G-protein-coupled cannabinoid receptors expressed on leukocytes, CB1 and CB2, has provided a putative mechanism of action for immune modulation
A C Herring et al.
The Journal of pharmacology and experimental therapeutics, 291(3), 1156-1163 (1999-11-24)
Cannabinol (CBN), an immunosuppressive cannabinoid and ligand for the peripheral cannabinoid receptor CB2, inhibits the cAMP signaling cascade in forskolin-stimulated thymocytes. The objective of the present studies was to further characterize the mechanism of CBN immune modulation by investigating its
Lucio Minuti et al.
The Journal of organic chemistry, 77(18), 7923-7931 (2012-08-24)
Diels-Alder reactions of a range of 1-(alkoxy/alkyl/halogen-substituted phenyl)buta-1,3-dienes with methyl propiolate carried out in a green ethanolic medium under 9 kbar pressure were investigated. The use of high pressure as activating method of the Diels-Alder reactions allows efficient and regioselective
Jonathan A Farrimond et al.
Psychopharmacology, 223(1), 117-129 (2012-05-01)
Increased food consumption following ∆(9)-tetrahydrocannabinol-induced cannabinoid type 1 receptor agonism is well documented. However, possible non-∆(9)-tetrahydrocannabinol phytocannabinoid-induced feeding effects have yet to be fully investigated. Therefore, we have assessed the effects of the individual phytocannabinoids, cannabigerol, cannabidiol and cannabinol, upon
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