Arvanil

Arvanil

Cayman Chemical Item Number 90052

N-Vanillylarachidonamide (CAS 128007-31-8)

Arvanil (CAS 128007-31-8)

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, 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.

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).

Synonyms

N-Vanillylarachidonamide

Formal Name

N-[(4-hydroxy-3-methoxyphenyl)methyl]-5Z,8Z,11Z,14Z-eicosatetraenamide

CAS Number

128007-31-8

Molecular Formula

C₂₈H₄₁NO₃

Formula Weight

439.6

Formulation

A solution in ethanol

Purity

>98%

λ_max

229, 281 nm

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCc1ccc(O)c(OC)c1

Background Reading

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).

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

Size

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5 mg 
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