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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

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

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 A Izzo et al.
Naunyn-Schmiedeberg's archives of pharmacology, 360(2), 221-223 (1999-09-24)
We have studied the effect of WIN 55,212-2 (a psychoactive cannabinoid agonist), cannabinol (a nonpsychoactive cannabinoid agonist), SR141716A, a cannabinoid CB1 antagonist, and SR144528, a cannabinoid CB2 antagonist, on gastric emptying in the rat. WIN 55,212-2 (0.1-5 mg/kg, i.p.) and
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
Penchal Reddy Nandaluru et al.
Organic letters, 14(1), 310-313 (2011-12-17)
A multicomponent domino reaction that affords 6H-dibenzo[b,d]pyran-6-ones is reported. The overall transformation consists of six reactions: Knoevenagel condensation, transesterification, enamine formation, an inverse electron demand Diels-Alder (IEDDA) reaction, 1,2-elimination, and transfer hydrogenation. Both the diene and dienophile for the key
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