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Submit Review(-)-Cannabidiol
Description: Natural cannabinoid; GPR55 antagonist, weak CB1 antagonist, CB2 inverse agonist and AMT inhibitor
Alternative Names: CBD
Chemical Name: 2-[(1R,6R)-3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1,3-benzenediol
Purity: ≥99% (HPLC)
Biological Activity for (-)-Cannabidiol
(-)-Cannabidiol is a non-psychotropic constituent of cannabis that is anticonvulsive, antihyperalgesic and neuroprotective in vivo. GPR55 and weak CB1 antagonist (IC50 values are 0.445 and 3.35 μM), CB2 receptor inverse agonist and inhibitor of anandamide uptake (IC50 = 27.5 μM). Also inhibits FABPs and a weak agonist at TRP vanilloid receptors (EC50 = 3.5 μM). Reduces inflammation and LPS-induced cytokine production in cultured microglial cells.
Technical Data for (-)-Cannabidiol
| M. Wt | 314.47 |
| Formula | C21H30O2 |
| Storage | Store at -20°C |
| Purity | ≥99% (HPLC) |
| CAS Number | 13956-29-1 |
| PubChem ID | 12302390 |
| InChI Key | QHMBSVQNZZTUGM-ROUUACIJSA-N |
| Smiles | CCCCCC1=CC(O)=C([C@H]2C=C(C)CC[C@H]2C(C)=C)C(O)=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for (-)-Cannabidiol
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 23.59 | 75 | |
| DMSO | 23.59 | 75 |
Preparing Stock Solutions for (-)-Cannabidiol
The following data is based on the product molecular weight 314.47. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.75 mM | 4.24 mL | 21.2 mL | 42.4 mL |
| 3.75 mM | 0.85 mL | 4.24 mL | 8.48 mL |
| 7.5 mM | 0.42 mL | 2.12 mL | 4.24 mL |
| 37.5 mM | 0.08 mL | 0.42 mL | 0.85 mL |
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Product Datasheets for (-)-Cannabidiol
References for (-)-Cannabidiol
References are publications that support the biological activity of the product.
Costa et al (2004) Vanilloid TRPV1 receptor mediates the antihyperalgesic effect of the nonpsychoactive cannabinoid, cannabidiol, in a rat model of acute inflammation. Br.J.Pharmacol. 143 247 PMID: 15313881
Petitet et al (1998) Complex pharmacology of natural cannabinoids: evidence for partial agonist activity of Δ9-tetrahydrocannabinol and antagonist activity of cannabidiol on rat brain cannabinoid receptors. Life Sci. 63 PL1 PMID: 9667767
Ryberg et al (2007) The orphan receptor GPR55 is a novel cannabinoid receptor. Br.J.Pharmacol. 152 1092 PMID: 17876302
Thomas et al (2007) Cannabidiol displays unexpectedly high potency as an antagonist of CB1 and CB2 receptor agonists in vitro. Br.J.Pharmacol. 150 613 PMID: 17245363
Deutsch (2016) A personal retrospective: Elevating Anandamide (AEA) by targeting fatty acid amide hydrolase (FAAH) and the fatty acid binding proteins (FABPs). Front.Pharmacol. 7 370 PMID: 27790143
Dos-Santos-Pereira et al (2020) Cannabidiol prevents LPS-induced microglial inflammation by inhibiting ROS/NF-?B-dependent signaling and glucose consumption. Glia 68 561 PMID: 31647138
If you know of a relevant reference for (-)-Cannabidiol, please let us know.
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Keywords: (-)-Cannabidiol, (-)-Cannabidiol supplier, Natural, cannabinoids, AMT, inhibitors, inhibits, GPR55, antagonists, weak, CB1, CB2, inverse, agonists, Anandamide, Transporters, Monoamine, Neurotransmitter, Non-Selective, Receptors, cb2r, cb1r, FABP, FABPs, fatty, acid, binding, proteins, CBD, Cannabinoid, Non-selective, Cannabinoids, Fatty, Acid, Binding, Proteins, 1570, Tocris Bioscience
5 Citations for (-)-Cannabidiol
Citations are publications that use Tocris products. Selected citations for (-)-Cannabidiol include:
Rodríguez-Muñoz et al (2018) Cannabidiol enhances MOR antinociception, diminishes NMDA-mediated seizures and reduces stroke damage via the sigma 1 receptor. Mol Brain 11 51 PMID: 30223868
Hamtiaux et al (2011) Increasing antiproliferative properties of endocannabinoids in N1E-115 neuroblastoma cells through inhibition of their metabolism. PLoS One 6 e26823 PMID: 22046372
Panja et al (2019) Paraneoplastic cerebellar degeneration: Yo antibody alters mitochondrial calcium buffering capacity. Neuropathol Appl Neurobiol 45 141 PMID: 29679372
Whyte et al (2009) The putative cannabinoid receptor GPR55 affects osteoclast function in vitro and bone mass in vivo. PLoS One 106 16511 PMID: 19805329
Esposito et al (2011) Cannabidiol reduces Aβ-induced neuroinflammation and promotes hippocampal neurogenesis through PPARγ involvement. Proc Natl Acad Sci U S A 6 e28668 PMID: 22163051
Do you know of a great paper that uses (-)-Cannabidiol from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
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Cannabinoid Receptor Ligands Scientific Review
Written by Roger Pertwee, this review discusses compounds which affect the activity of the endocannabinoid system, focusing particularly on ligands that are most widely used as experimental tools and denotes compounds available from Tocris.