A structural analog of capsaicin
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Olvanil

Item No. 90262

Technical Information
Formal Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]-9Z-octadecenamide
CAS Number
58493-49-5
Synonyms
  • NE 19550
  • N-Vanillyloleamide
Molecular Formula
C26H43NO3
Formula Weight
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
0.1 M Na2CO3: 1 mg/mlDMF: 15 mg/mlDMSO: 13 mg/mlEthanol: 31 mg/ml
λmax
229, 281 nm
SMILES
CCCCCCCC/C=C\CCCCCCCC(N([H])CC1=CC(OC)=C(O)C=C1)=O
InChi Code
InChI=1S/C26H43NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26(29)27-22-23-19-20-24(28)25(21-23)30-2/h10-11,19-21,28H,3-9,12-18,22H2,1-2H3,(H,27,29)/b11-10-
InChi Key
OPZKBPQVWDSATI-KHPPLWFESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Olvanil is a structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum genus. It is the amide of vanillylamine and oleic acid. Olvanil acts as an agonist at the vanilloid receptor, VR1, inducing desensitization analgesia in rat and mouse models of pain.1 Olvanil has complex interactions with the cannabinoid system, in that it potentiates the agonist activity of endogenous cannabinoids by inhibiting the reuptake of arachidonyl ethanolamide (AEA). Olvanil is a more potent reuptake inhibitor than AM404, which is commonly used for this purpose (50% inhibition of reuptake at 10 µM versus 12% for AM404 at the same dose).2 Olvanil is also a CB1 agonist, but does not bind to CB2 receptors or inhibit fatty acid amide hydrolase. The overall activity of olvanil in most models is that of an analgesic, but it is unclear how these effects are mediated by VR1, the CB1 receptor, or other components of the endogenous pain sensation system.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Janusz, J.M., Buckwalter, B.L., Young, P.A., et alVanilloids. 1. Analogs of capsaicin with antinociceptive and antiinflammatory activity. J. Med. Chem. 36, 2595-2604 (1993).

    2. Di Marzo, V., Bisogno, T., Melck, D., et alInteractions between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett. 436, 449-454 (1998).