A TRPV1 agonist
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Palvanil

Item No. 46656

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]-hexadecanamide
CAS Number
69693-13-6
Synonyms
  • N-palmitoyl Vanillamide
Molecular Formula
C24H41NO3
Formula Weight
391.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/mlEthanol: Slightly soluble: 0.1-1 mg/ml
SMILES
CCCCCCCCCCCCCCCC(NCC1=CC=C(O)C(OC)=C1)=O
InChi Code
InChI=1S/C24H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24(27)25-20-21-17-18-22(26)23(19-21)28-2/h17-19,26H,3-16,20H2,1-2H3,(H,25,27)
InChi Key
SGEUEXJZQFSBNX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $199

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    5 mg

    $448

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    10 mg

    $796

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    25 mg

    $1,741

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    Cayman Chemical
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    Product Description

    Palvanil is an agonist of transient receptor potential vanilloid 1 (TRPV1) and a derivative of capsaicin (Item Nos. 92350 | 10010743).1 It increases intracellular calcium levels in HEK293 cells expressing human TRPV1 (EC50 = 5 nM). Palvanil also selectively binds to the cannabinoid 1 (CB1) receptor over the CB2 receptor (Kis = 3 and >15 µM, respectively).2 Unlike olvanil (Item No. 90262) and arvanil (Item No. 90052), palvanil does not inhibit anandamide (arachidonoyl ethanolamide; Item No. 90050) transport into RBL-2H3 cells (IC50 = >50 µM). Palvanil inhibits the proliferation of MCF-7, EFM-19, and T47D breast cancer cells (IC50s = 2.2, 1, and 1.6 µM, respectively). It increases whole gastrointestinal (GI) transit time in mice and has antinociceptive activity in a mouse model of visceral pain at 1 mg/kg.3 Palvanil (0.05 and 0.1 mg/kg) also decreases immobility time in the forced swim test in rats.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. De Petrocellis, L., Bisogno, T., Davis, B.J., et al. Overlap between the ligand recognition properties of the anandamide transporter and the VR1 vanilloid receptor: Inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett. 483(1), 52-56 (2000).

    2. Melck, D., Bisogno, T., De Petrocellis, L., et al. Unsaturated long-chain N-acyl-vanillyl-amides (N-AVAMs): Vanilloid receptor ligands that inhibit anandamide-facilitated transport and bind to CB1 cannabinoid receptors. Biochem. Biophys. Res. Commun. 262(1), 275-284 (1999).

    3. Szymaszkiewicz, A., Włodarczyk, J., Wasilewski, A., et al. Desensitization of transient receptor potential vanilloid type-1 (TRPV1) channel as promising therapy of irritable bowel syndrome: Characterization of the action of palvanil in the mouse gastrointestinal tract. Naunyn Schmiedebergs Arch. Pharmacol. 393(8), 1357-1364 (2020).

    4. Reyes-Mendez, M.E., Castro-Sánchez, L.A., Dagnino-Acosta, A., et al. Capsaicin produces antidepressant-like effects in the forced swimming test and enhances the response of a sub-effective dose of amitriptyline in rats. Physiol. Behav. 195, 158-166 (2018).