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Arvanil

N-Vanillylarachidonamide

An Agonist of TRPV1 Channels and a Ligand of CB1 Receptors

Cat #: A-335
Alternative Name N-Vanillylarachidonamide
  • Bioassay Tested
    • Source Synthetic
    MW: 439.64
    Purity: >96% (HPLC)
    Effective concentration 1 nM – 1 µM.
    Structure
    Chemical name (5Z,8Z,11Z,14Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]icosa-5,8,11,14-tetraenamide.
    Molecular formula C28H41NO3.
    CAS No.: 128007-31-8
    PubChem CID 6449767
    Activity Arvanil is an agonist of TRPV1 channels (EC50 = 0.5 nM), a ligand of CB1 receptors (Ki = 0.25-0.5 μM), and an inhibitor of anandamide accumulation (IC50 = 3.6 µM). In vivo it demonstrates vasodilator, analgesic, and anti-inflammatory properties. Arvanil inhibits human breast cancer cell proliferation and the growth of astrocytoma xenograft tumors in mice1-3.
    References-Activity
    1. Melck, D. et al. (1999) Biochem. Biophys. Res. Commun. 262, 275.
    2. Di Marzo, V. et al. (2000) Eur. J. Pharmacol. 406, 363.
    3. Di Marzo, V. et al. (2002) J. Pharmacol. Exp. Ther. 300, 984.
    Shipping and storage Shipped at room temperature. Product as supplied can be stored intact at room temperature for several weeks. For longer periods, it should be stored desiccated at -20°C.
    Solubility Soluble in ethanol and DMSO. Centrifuge all product preparations before use (10000 x g 5 min).
    Storage of solutions Up to four weeks at 4°C or three months at -20°C.
    Our bioassay
    • Alomone Labs Arvanil activates TRPV1 channels expressed in rat C6 glioma cells.
      Alomone Labs Arvanil activates TRPV1 channels expressed in rat C6 glioma cells.
      mTRPV1-C6 cells were loaded with Fluo-3 AM. Changes in intracellular Ca2+ were detected as changes in Fluo-3 signal following agonist application. Normalized fluorescence before and after application (at 20 seconds, arrow) of control solution, 5 nM and 500 nM Arvanil (#A-335), as indicated.
    References - Scientific background
    1. Melck, D. et al. (1999) Biochem. Biophys. Res. Commun. 262, 275.
    2. Sancho, R. et al. (2003) Br. J. Pharmacol. 140, 1035.
    3. Gentile, A. et al. (2016) J. Neuroinflammation 13, 231.
    4. McLeod, R.L. et al. (2006) Cough 2, 10.
    Scientific background

    Arvanil (N-Vanillylarachidonamide) is an agonist of TRPV1 channels and a ligand of CB1 cannabinoid receptors. Arvanil is a structural hybridization between the arachidonoyl group of anandamide (CB1 receptor ligand) and the vanillyl moiety of capsaicin1,2. Arvanil shows an EC50 value of 0.5 nM for TRPV1 receptors, and an IC50 value of 3.6 µM as an inhibitor of anandamide accumulation1.

    Studies have found that arvanil has the ability to induce dose-dependent apoptosis in the lymphoid Jurkat T-cell line2.

    CB1 receptors are important regulators of excitatory and inhibitory synaptic transmission in different areas in the brain. The receptor plays a crucial role in multiple sclerosis disease course and in mood control3.

    TRPV1 receptors are highly expressed in primary nociceptors. These channels can be activated by several stimuli such as heat, acid, certain arachidonic acid derivatives and direct phosphorylation via PKC4.

    Target TRPV1 channels, CB1 receptors
    Last update: 02/01/2022

    Arvanil (#A-335) is a highly pure, synthetic, and biologically active compound.

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    For research purposes only, not for human use
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