| Size | Price | Stock | Qty |
|---|---|---|---|
| 500μg |
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| 1mg | |||
| Other Sizes |
| Targets |
Target: Cannabinoid Receptor 2 (CB2). beta-Caryophyllene is a selective full agonist of the CB2 receptor (Ki ≈ 150-200 nM), with negligible affinity for the CB1 receptor (>1000-fold selectivity). CB2 receptors are primarily expressed on immune cells and are involved in modulating inflammation, pain, and immune responses. The deuterated standard has no biological activity and is used for analytical purposes.
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|---|---|
| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
In vitro, the labeled standard has no direct biological activity. The unlabeled beta-caryophyllene (1-20 uM) activates the CB2 receptor in CB2-transfected cells, inhibiting forskolin-stimulated cAMP accumulation (IC50 ~150 nM). It also inhibits LPS-induced pro-inflammatory cytokine production (TNF-alpha, IL-1beta, IL-6) in microglial cells and macrophages, reducing inflammation via CB2 activation. No direct cytotoxicity is observed at concentrations up to 50 uM. |
| ln Vivo |
In vivo, the unlabeled beta-caryophyllene (10-100 mg/kg, oral or IP) is orally active and produces anti-inflammatory, analgesic, and neuroprotective effects in animal models. It reduces edema in carrageenan-induced paw inflammation, attenuates mechanical allodynia and thermal hyperalgesia in neuropathic pain models, and reduces ischemic damage in stroke models. It does not produce psychoactive effects because it does not activate CB1 receptors. The deuterated standard is not administered for efficacy studies but is used to quantify beta-caryophyllene in PK studies.
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| Enzyme Assay |
For cell-free assays (LC-MS/MS): plasma, serum, or tissue homogenates are spiked with beta-Caryophyllene-d2 internal standard. After liquid-liquid extraction (e.g., with hexane or ethyl acetate) and centrifugation, the organic layer is evaporated and reconstituted in mobile phase. Analysis is performed by GC-MS or LC-MS/MS. Quantitation of beta-caryophyllene is based on the analyte/internal standard peak area ratio. The deuterated standard co-elutes with the unlabeled analyte, enabling accurate quantification and correction for extraction recovery and matrix effects.
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| Cell Assay |
For cell-based assays: CB2-expressing cells (e.g., CB2-transfected CHO or HEK293 cells) are loaded with a cAMP detection reagent, treated with beta-caryophyllene (0-100 uM, 30 min), and stimulated with forskolin. cAMP levels are measured by HTRF or AlphaScreen. Activation of CB2 is confirmed by inhibition of cAMP accumulation. Alternatively, microglial cells (BV-2) are treated with LPS (1 ug/mL) in the presence or absence of beta-caryophyllene (1-20 uM), and TNF-alpha and IL-6 levels in the supernatant are measured by ELISA. The labeled standard is not used in these assays.
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| Animal Protocol |
For in vivo animal studies: rodents (mice or rats) are administered beta-caryophyllene by oral gavage (10-100 mg/kg) or intraperitoneal injection (10-50 mg/kg). Serial blood samples are collected, and plasma is processed with beta-Caryophyllene-d2 internal standard for LC-MS/MS analysis to determine PK parameters (Cmax, Tmax, t1/2, AUC). For pharmacodynamic studies, animals are subjected to inflammation or pain models (e.g., carrageenan paw edema, formalin test, CFA-induced hyperalgesia). Tissues (brain, liver, spleen, plasma) are collected at various time points and analyzed for beta-caryophyllene concentrations and CB2 target engagement. The labeled standard is used in bioanalysis but not administered to animals directly.
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| ADME/Pharmacokinetics |
PK properties of beta-caryophyllene: After oral administration in rodents, it is rapidly absorbed (Tmax 0.5-2 h) and distributed to tissues, including the brain (crosses the blood-brain barrier due to its lipophilicity). Oral bioavailability is moderate (20-40%). Plasma half-life is 2-5 h. It is extensively metabolized by CYP450 enzymes (primarily CYP2C19 and CYP3A4) to various oxidized metabolites (e.g., beta-caryophyllene epoxide). Excretion occurs mainly via feces and urine. The deuterated standard does not exhibit distinct PK behavior and is used exclusively as an analytical internal standard.
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| Toxicity/Toxicokinetics |
No toxicity data are reported for the deuterated standard. Unlabeled beta-caryophyllene is considered safe and is generally recognized as safe (GRAS) by the FDA as a food flavoring agent. In animal studies, no significant toxicity is observed at doses up to 1000 mg/kg. High doses may cause mild sedation, but no organ toxicity or adverse effects on reproduction have been reported. The labeled compound is for research use only and is non-hazardous for transport.
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| References |
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| Additional Infomation |
beta-Caryophyllene-d2 is a research standard and is not an approved drug. The unlabeled beta-caryophyllene is a natural product found in foods and dietary supplements. It has not received FDA approval as a drug, but it is being investigated in preclinical studies for various therapeutic indications, including inflammatory diseases (arthritis, IBD, asthma), pain (neuropathic pain, inflammatory pain), neurodegenerative diseases (Alzheimer‘s, Parkinson's, multiple sclerosis), and as an anticancer agent. The labeled standard is used for analytical method development and PK studies of beta-caryophyllene and CB2 agonists. It is an essential tool for stable isotope dilution assays in natural product research and phytopharmaceutical quality control.
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| Molecular Formula |
C15H24
|
|---|---|
| Molecular Weight |
204.351064682007
|
| Exact Mass |
206.2
|
| CAS # |
2006272-96-2
|
| Related CAS # |
β-Caryophyllene;87-44-5
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| PubChem CID |
163322627
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| Appearance |
Colorless to light yellow ointment
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| LogP |
4.4
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
15
|
| Complexity |
293
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| Defined Atom Stereocenter Count |
2
|
| SMILES |
[2H]C(=C1CC/C=C(\CC[C@@H]2[C@@H]1CC2(C)C)/C)[2H]
|
| InChi Key |
NPNUFJAVOOONJE-DUOVYBGSSA-N
|
| InChi Code |
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1/i2D2
|
| Chemical Name |
(1R,4Z,9S)-8-(dideuteriomethylidene)-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
|
| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8936 mL | 24.4678 mL | 48.9356 mL | |
| 5 mM | 0.9787 mL | 4.8936 mL | 9.7871 mL | |
| 10 mM | 0.4894 mL | 2.4468 mL | 4.8936 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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