| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
Virodhamine targets cannabinoid CB1 and CB2 receptors, as well as GPR55. At CB1 receptors, it acts as a partial agonist/antagonist, while at CB2 receptors it acts as a full agonist. It is also a full agonist at GPR55 with an EC50 of 12 nM. The compound's mixed agonist/antagonist profile at CB1 receptors and full agonist activity at CB2 receptors distinguishes it from other endocannabinoids. Virodhamine induces megakaryocyte differentiation by triggering MAPK signaling and ROS production.
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| ln Vitro |
Adherence, membrane expansion, and nucleus size are all increased by viteodhamine (50 nM; 72 hours)[1]. Virodhamine (10–40 μM; 72 h) raises TRPV1 and CD61 expression levels[1]. Virodhamine (72 hours) dramatically raises the percentage of high ploidy cells relative to control and inhibits the proliferation of megakaryocyte cells[1]. In megakaryocytic cells, virodhamine dramatically raises the expression of the CB2 receptor protein, ROS generation, and NAPDH oxidase NOX4[1].
In vitro, Virodhamine acts as a full agonist at GPR55 and CB2 receptors with EC50 values of 12 nM and 381 nM, respectively, and as a partial agonist/antagonist at CB1 receptors with an EC50 of 2920 nM. The compound induces megakaryocyte differentiation by triggering MAPK signaling and ROS production. It modulates neurotransmission by activating cannabinoid receptors. Standard in vitro assays include receptor binding studies, cAMP accumulation assays, and measurement of MAPK signaling pathway activation. The compound's unique receptor profile makes it a valuable tool for studying cannabinoid receptor pharmacology. |
| ln Vivo |
Virodhamine (1-10 mg/kg; ip once) restores the nicotine (0.8 mg/kg) and immobilization stress caused anxiety in vivo[2].
In vivo, Virodhamine induces hypothermia, a characteristic effect of cannabinoid receptor activation. As an endocannabinoid found in higher concentrations peripherally than anandamide, it may play physiological roles in peripheral tissues. The compound has been studied for potential applications in Alzheimer's disease and other neurological disorders. However, comprehensive in vivo pharmacological studies are limited. Given its CB1 antagonist/CB2 agonist profile, it may produce distinct effects from other endocannabinoids. Further studies are needed to fully characterize its in vivo activity. |
| Enzyme Assay |
For non-cell-based receptor binding assays, Virodhamine can be evaluated using membrane preparations from cells expressing human CB1, CB2, or GPR55 receptors. Radioligand binding displacement experiments are performed using [3H]-CP55940 for CB1/CB2 or [3H]-LPI for GPR55. Membrane homogenates are incubated with increasing concentrations of the test compound and a fixed concentration of the radioligand at 30°C for 60-90 minutes. Bound radioligand is separated from free by filtration through GF/B filters. Nonspecific binding is determined in the presence of excess unlabeled ligand. Ki or IC50 values are calculated from displacement curves using nonlinear regression analysis.
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| Cell Assay |
RT-PCR[1]
Cell Types: Megakaryocyte cell line Tested Concentrations: 10, 20 and 40 μM Incubation Duration: 72 h Experimental Results: Dose-dependently enhanced the expression level of megakaryocytic marker CD61 and the expression of TRPV1 mRNA. For in vitro cellular assays, cells expressing CB1, CB2, or GPR55 receptors are cultured in appropriate media. For G protein activation assays, [35S]GTPγS binding is measured in membrane preparations. For cAMP accumulation assays, cells are pre-incubated with forskolin to stimulate cAMP production, then treated with various concentrations of Virodhamine. cAMP levels are measured using ELISA or HTRF-based detection. For MAPK signaling assays, cells are treated with the compound and phosphorylation of ERK1/2 is measured by Western blot. For megakaryocyte differentiation assays, cells are treated and differentiation markers are assessed. |
| Animal Protocol |
Animal/Disease Models: Male ICR mice with nicotine (0.8 mg/kg) and immobilization stress induced anxiety[2]
Doses: 1, 5 and 10 mg/kg Route of Administration: intraperitoneal (ip) injection; 1-10 mg/kg; once Experimental Results: Dramatically repaired the working memory impairment-like behaviors at a does of 5 mg/kg and demonstrated significant anxiolytic-like effects against the anxiety-like behaviors at a does of 10 mg/kg. For in vivo animal studies, Virodhamine can be administered to rodents via intraperitoneal injection. Body temperature is monitored using rectal thermometers to assess hypothermia. In models of neurological disorders, behavioral tests (e.g., open field, elevated plus maze, Morris water maze) may be performed. In pain models, nociceptive responses are measured. In inflammation models, inflammatory markers are assessed. Dosing regimens vary depending on the specific model. Blood and tissue samples may be collected for pharmacokinetic analysis. |
| ADME/Pharmacokinetics |
The pharmacokinetic properties of Virodhamine have not been extensively characterized. As an endogenous fatty acid amide, it is expected to be highly lipophilic with good tissue penetration. It is likely rapidly metabolized by fatty acid amide hydrolase (FAAH) and other enzymes. The compound is available in ethanol solution for research use. Comprehensive ADME studies would be needed for full pharmacokinetic characterization. The compound should be stored at -20°C for long-term stability.
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| Toxicity/Toxicokinetics |
The toxicity profile of Virodhamine has not been extensively reported. As an endogenous compound, it is expected to have a favorable safety profile at physiological concentrations. At pharmacological doses, potential adverse effects may include those associated with cannabinoid receptor activation, such as hypothermia, sedation, and cognitive impairment. The compound is for research use only and not for human consumption. Standard toxicological evaluation would include acute and repeated-dose toxicity studies.
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| References |
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| Additional Infomation |
O-arachidonic acid ethanolamine is a fatty acid ester.
Virodhamine (O-arachidonoyl ethanolamine) is an endogenous cannabinoid that acts as a CB1 receptor antagonist and CB2 receptor agonist. It is found in higher concentrations peripherally than anandamide. The compound is a full agonist at GPR55 and CB2 receptors and a partial agonist/antagonist at CB1 receptors. It induces hypothermia in vivo and has been studied for potential applications in Alzheimer's disease and other neurological disorders. Virodhamine is available for research purposes only and is not approved for clinical use. |
| Molecular Formula |
C22H37NO2
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| Molecular Weight |
347.53
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| Exact Mass |
347.282
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| Elemental Analysis |
C, 76.03; H, 10.73; N, 4.03; O, 9.21
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| CAS # |
287937-12-6
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| Related CAS # |
287937-12-6; 1415264-56-0; 443129-35-9
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| PubChem CID |
5712057
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| Appearance |
Yellow to brown viscous liquid
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| LogP |
6.334
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
17
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| Heavy Atom Count |
25
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| Complexity |
408
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCC/C=C/C/C=C/C/C=C/C/C=C/CCCC(OCCN)=O
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| InChi Key |
DLHLOYYQQGSXCC-DOFZRALJSA-N
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| InChi Code |
InChI=1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15-
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| Chemical Name |
2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
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| Synonyms |
virodhamine; O-arachidonoyl ethanolamine; 287937-12-6; 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate; 2-aminoethyl-5Z,8Z,11Z,14Z-eicosatetraenoate;
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| 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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (287.74 mM)
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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 | 2.8774 mL | 14.3872 mL | 28.7745 mL | |
| 5 mM | 0.5755 mL | 2.8774 mL | 5.7549 mL | |
| 10 mM | 0.2877 mL | 1.4387 mL | 2.8774 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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