A structural analog of capsaicin with analgesic activity
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Isomer(s)
90057N-Arachidonoyl Dopamine
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Arvanil

Item No. 90052

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(4-hydroxy-3-methoxyphenyl)methyl]-5Z,8Z,11Z,14Z-eicosatetraenamide
CAS Number
128007-31-8
Synonyms
  • N-Vanillylarachidonamide
Molecular Formula
C28H41NO3
Formula Weight
439.6
Purity
≥98%
Formulation
A 50 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
0.1M Na2CO3: 1 mg/mlDMF: 15 mg/mlDMSO: 13 mg/mlEthanol: 31 mg/ml
λmax
229, 281 nm
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCc1ccc(O)c(OC)c1
InChi Code
InChI=1S/C28H41NO3/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-28(31)29-24-25-21-22-26(30)27(23-25)32-2/h7-8,10-11,13-14,16-17,21-23,30H,3-6,9,12,15,18-20,24H2,1-2H3,(H,29,31)/b8-7-,11-10-,14-13-,17-16-
InChi Key
QVLMCRFQGHWOPM-ZKWNWVNESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $38

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    10 mg

    $71

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    50 mg

    $291

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    100 mg

    $505

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    Product Description

    Arvanil is a structural analog of capsaicin, which is the noxious active component of hot peppers of the Capsicum family. It is the amide of vanillylamine and arachidonic acid. Arvanil induces analgesia in rat and mouse models of pain.1 Arvanil has complex interactions with the cannabinoid system, in that it potentiates the agonist activity of endogenous cannabinoids by inhibiting the reuptake of arachidonoyl ethanolamide (AEA). It is an agonist at CB1 (Ki values of 0.25 to 0.52 μM), but not CB2, receptors, and is resistant to hydrolysis by FAAH.2 The vasodilator, analgesic, and anti-inflammatory properties of arvanil are not clearly explained by its interactions with cannabinoid and vanilloid receptors, suggesting other possible sites of action.

    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 al. Vanilloids. 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 al. Interactions between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett. 436, 449-454 (1998).