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Merck

C6888

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
NACRES:
NA.24
PubChem Substance ID:
329775137
UNSPSC Code:
41116107
MDL number:
MFCD00056774

Key Documents

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Product Name

Cannabinol, analytical standard

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

SMILES string

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

InChI key

VBGLYOIFKLUMQG-UHFFFAOYSA-N

grade

analytical standard

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

Quality Level

100

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

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

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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
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
Dayong Lee et al.
Clinical chemistry, 57(8), 1127-1136 (2011-06-17)
Oral fluid (OF) is an accepted alternative biological matrix for drug treatment, workplace, and DUID (driving under the influence of drugs) investigations, but establishing the cannabinoid OF detection window and concentration cutoff criteria are important. Cannabinoid concentrations were quantified in
Spyros P Nikas et al.
Journal of medicinal chemistry, 53(19), 6996-7010 (2010-10-12)
In pursuit of a more detailed understanding of the structural requirements for the key side chain cannabinoid pharmacophore, we have extended our SAR to cover a variety of conformationally modified side chains within the 9-keto and 9-hydroxyl tricyclic structures. Of
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